How to Dress Your Age: Balancing Style with Maturity

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Look Great At Any Age With Our Advice!

It is likely that you have, at some point in your life, been told to “dress your age.” But what does that actually mean? In this guide, we will explain how to dress appropriately for your age and why doing so can greatly benefit your personal style, confidence, and how others perceive you.

After all, perhaps you’ve seen middle-aged people trying to dress like teenagers, and the effect has been anything but positive. Or perhaps you’ve seen young men in stuffy suits that make them look muddled, not mature. With this guide, you needn’t worry about age-appropriateness ruining your looks ever again!

Photo of Thomas Mann

“One fellow, in a bright yellow summer suit of ultra-fashionable cut, with a red necktie, and a rakishly tilted panama, surpassed all the others in his crowing good humour. But as soon as Aschenbach looked at him a bit more carefully, he discovered with a kind of horror that the youth was a cheat. He was old, that was unquestionable. There were wrinkles around his eyes and mouth. The faint crimson of the cheeks was paint, the hair under his brilliantly decorated straw hat was a wig; his neck was hollow and stringy, his turned-up moustache and the imperial on his chin were dyed; the full set of yellow teeth which he displayed when he laughed, a cheap artificial plate; and his hands, with signet rings on both index fingers, were those of an old man.”

From Death in Venice by Thomas Mann

Avoid these dressing mistakes some older men make!

Why Dressing Your Age Matters

Dressing Your Age Is Harder To Do Now Than Ever Before

The challenge of pinpointing how you should dress at a certain age is manifold: the world has gotten more and more casual, there are more than a few clothing options on the market, clothes have become more affordable, and people in the same age group might have nothing more in common than the number of years they’ve been alive.

However, taking the time to dress your age can offer many important benefits, both in how you feel about yourself and in how others perceive you. Understanding these benefits will help you determine whether or not it makes sense for you to dress according to the conventions of your age.

Illustration of a young man in an ill-fitting suit
Even Classic Clothing, if not properly fitted or suited to your age, can appear odd when worn. In this case, the overly broad shoulders and cut around the chest of this double-breasted suit does not flatter the young, slim frame of the wearer. [Image Credit: Robert Looser, PKZ]

Why You Should Dress Your Age

Nathan has been with the Gentleman's Gazette since mid-2021.

To Cultiaves Your Best Possible Perception

Dressing your age is fundamentally a matter of perception. It is not about you, but rather about how other people see you. Other people will perceive you in a certain light based on what they think your age is and how you dress. The question is, do you care? For most men, the answer is yes. In business, dressing to show that you understand the basic style staple pieces associated with your age makes it clear that you are a self-aware, realistic person: this usually makes future clients more comfortable doing business with you. If you work in an office, a dress code might require you to dress a certain way to fit in, be taken seriously, and get ahead. As you’ve probably heard us say before, there are many benefits to dressing up in an age when most people dress down. The key to dressing your age is to balance how you want to be perceived with your age and maturity.

Kyle in a casual yet timeless look in the Minnesota fall

To Inspires Confidence

As with many Classic Style conventions, dressing according to the standards of your age is not meant to be a punitive requirement, but a helpful guideline. As you grow older, expanding your wardrobe beyond a pair of jeans and graphic tees will help you look more mature and experienced at the same time that you are becoming more mature and gaining experience. Essentially, your clothing choices will more closely match the realities of your life and what you are doing with it. This consummate connection between appearance and development usually inspires confidence, because if you “look the part” of a successful, accomplished person that is your age, you are more likely to feel successful and accomplished, and, therefore, more confident generally.

Jack holding a fence and being himself

To Enjoy the Benefits of Every Age

Life is a journey with many different chapters, and dressing according to the conventions of your age group will provide more opportunities for varied and unique styles. By alligning your clothing according to your age, not only are you benefiting from garments that are more likely to suit the realities of your life, you are able to experience an even wider array of clothing and style options. Why settle for t-shirts your whole life when a tee isn’t the best compliment for an older body, and so many other more flattering casual clothes exist to benefit an older man? Essentially, like seasonal dressing, dressing your age allows you to more fully enjoy all of the unique aspects of your life.

Learn to savor the seasons like Italians do!

Dressing too young for your age can often have the wrong effect

Dressing Your Age is Your Choice

If you have the ability to dress in a style all your own, regardless of your age and regardless of how others perceive you, then embrace it!

If, however, you think that what we have highlighted so far makes it clear that you would benefit from learning how to dress your age, then read on, because this guide is for you. And, even if you prefer to dress in a way different from your age, this guide can help illustrate to you stylish dressing conventions appropriate to every age group.

Dressing Your Age FAQ

What does “dressing your age” mean?

“Dressing your age” refers to assembling and wearing outfits that are consummate with your current stage in life, relative to your age. Conventionally, individual age groups dressed in a somewhat similar overall style because members of that age group were in the same general stage of life. This meant they were at comparable levels professional, had access to similar funds, and had roughly comparable body types. The standards of dressing associated with each age were developed, broadly speaking, to flatter the appearance of men of that age group and to fit in with the activities and standards associated with those age groups.

What are the benefits of dressing your age?

There are three broad benefits to dressing your age. The first is that, in fulfilling the conventional appearance of your age group, you will be better able to inspire confidence in others that you are secure about yourself and your age and recognize the realities of being the age that you are. This awareness generally imparts a more positive perception than those in denial about their age. Secondly, dressing according to age conventions that have, for centuries, benefited men in your age group will usually help you feel more confident, no matter how old you are: these traditions arose for a reason, and “if it ain’t broke, don’t fix it!” Finally, dressing your age encourages you to experiment with a wider range of styles that are suited to your particular time of life. Essentially, like seasonal dressing, dressing your age allows you to more fully enjoy all of the unique aspects of your life.

Do you have to dress your age?

No, you do not. While there are many benefits to dressing your age, the choice is entirely your own. If you are not concerned with how others perceive you or want to encourage a very particular perception, and you are confident enough to pull it off, you can dress according to the conventions of any age group you desire, regardless of your actual age.

Is it better to dress to appear younger or older than you are?

When you are younger, dressing to appear older might make you feel more mature and confident. When you are older, dressing to appear younger might make you feel more vigorous and adventurous, and also more confident. Ultimately, what matters is that you dress in a way that makes you feel confident, regardless of what age you are. In many cases, dressing according to the standards of your actual age is a great way to achieve this.

How do I dress well at any age?

Dressing well requires a combination of impeccable fit, versatile styling options, awareness of formality, and confidence in your personal style. Fortunately, we cover all of these topics here at The Gentleman’s Gazette. Taking care to also follow the conventional dressing standards of your age group will also help you look great at any age, and that is exactly what this guide will teach you how to do.

How To Dress Your Age

Be Guided By These Fundamental Questions

When you are determining how best to dress your age, asking yourself the following questions will help you frame what “age-appropriate” dress means and looks like for you. Taking the time to truly consider these questions while planning an outfit will ensure that your ensembles appear unique and creative, and not just copied from age-restricted styles or conventions.

Ask Yourself…

1
Preston thoughtfully considering an idea.

How do I want people to perceive me?

Do I want to look older, younger, my age? Do I want to appear successful, artsy, exotic, mysterious, etc.? Make this your primary consideration when choosing what to wear.

2
Photo of a man in a white suit

Do I want to stand out or fit in?

Decide what your goals are for your style; is it to be the best-dressed guy in the room? Is it to look confident in the office? Is it to look like you fit into your environment?

3
OLYMPUS DIGITAL CAMERA

What do I want from my wardrobe?

 Is it to be up-to-date and trendy? Is it to have a wardrobe that stands the test of time?

4
Chris and Kyle in simple minimalist outfits

How do I want to feel when I get dressed?

Is it youthful, mature, dapper, or confident? Do I want to be taken more seriously?

Style Conventions By Age Group

Having pondered the above considerations, you are now better prepared to decide how you can incorporate the styling conventions of your age group into your personal style. Below, you will find our generalizations and tips on how to dress well according to the standards of your age group.

This advice is intended to be helpful, not constraining, so if you disagree with a point or find that it does not work for you, do not fret. None of these guidelines will work perfectly for everyone, but every tip will provide you with useful insight as you determine what works best for you.

Dressing Your Age: Young Men (Under 25)

Leverage Your Youthful Appearance

Illustration of three men, including two young men
The styling of young men is often influenced by the look of their elders but with a more casual air suitable to youth.

As you now have the money and capacity to fully control your own wardrobe, you finally have the chance to completely shape your own style. You can get away with pretty much any look at this age, but if perception matters to you, now is the best time to start building a wardrobe that works for you, rather than against you. You may not see the point of dressing up, but if being taken seriously is important to you at this age, consider doing it more.

A photograph of William Faulkner

“It’s terrible to be young. It’s terrible. Terrible.”

William Faulkner

At this age, you can take advantage of your youthful appearance to experiment. On the other hand, you want to be taken seriously as a newly-minted adult. Unless you’re going to a job interview, a wedding, or a funeral, you should not feel the need to wear a jacket and tie every single day. Instead, here are some tips for successfully mixing youth with maturity-boosting style.

Tips for Dressing Well When Under 25

  • Experiment! At this stage in your life, you can take bigger risks while looking for a style that really resonates with you.
  • Start having your clothes altered. Your body shape will likely change in the future, but now if the time to start learning about fit. Almost any garment can be improved with alterations. To learn more, check out our alterations guide here.
  • Start learning to put your own style preferences first. Regardless of the look you like, now that you are an adult, you should learn to dress for your own purposes rather than for other people’s, including your family and friends. Unless you’re not adhering to basic rules of decency and etiquette, don’t let mean-spirited comments about your style change what you wear.
  • Keep your pants well-fitting, modern, and simple. Chinos, dark wash denim, and cords will make you look mature but still youthful. Avoid fit extremes such as super-tight pants and excessively baggy tops, which will make you look insecure. Experiment and learn what cuts, colors, and fits flatter you the best.
  • Button-down shirts are your friend. Particularly in checks, plaids, and stripes, which are youthful patterns that will help balance out the more mature silhouette of a button-down. Tuck it in for a more mature look, or leave it untucked.
  • Skip the rips, tears, paint splatters, and acid washes. If you like those kind of details, our style probably isn’t for you, and they will make you look younger than you are.
  • Buy your first watch. Nowadays, watches are fun accessories rather than necessities, but they will make a youthful appearance look more mature in an instant. Check out Timex, Fossil or Nixon, but make sure to keep the case size proportional to your wrist. We recommend 42mm and under, and smaller if you have thin wrists. If you want to wear something more youthful, consider a chronograph or sports watch, even if you’ll never use it.
Photo of a young Frank Sinatra

Classic Style Icon of this age

Frank Sinatra

Frank Sinatra was a style icon his entire life, and that included his teenage years when he first began performing. Young Sinatra encapsulated everything that is fun and youthful about dressing well: he experimented with bold colors and unique garments that still appeared neat and flattering on casual occasions, and he knew how to dress up when it was expected of him.

Dressing Your Age: Early-to-Mid-Twenties

Embrace Seriousness without Sacrificing Style

1960s fashion illustration of younger men's fashion
Even as you’re getting older, you can stay young at heart.

At this age, you’re likely to start experiencing a need for more professional clothing. Being young is no longer an excuse to be underdressed, and at this age it will start to be held against you. You’re either in college or getting that first big job; now it’s time to dress for the career you want.

There’s no excuse for not owning a suit anymore. You’ll need one at some point, even if you work in a casual environment like a workshop or design studio. You’ll also need a blazer. Aside from that, the recommendations above for teenagers will work well too. Slowly begin to transition into a more mature style if you can, but it doesn’t mean having to dress like your dad. Here are some tips:

Consider this when buying your first suit!

Tips for Dressing Well in Your Early-to-Mid-Twenties

  • Buy your first suit. If you don’t already have one, that is. Get your first suit if you don’t already have it. Forget black. The adage that every man needs a black suit is a myth. Instead, opt for navy or charcoal. Patterns are easily remembered, so unless you’ve already built up a collection, skip them for now. If it is your first suit, consider a single-breasted suit with a notch lapel. If it’s your second or third, add a touch of sophistication and class with a double-breasted suit and a peak lapel.
  • Get a blazer, too. You might not be comfortable wearing a suit on a regular basis, but a blazer is much more versatile and relaxed. A good blazer will leave you prepared for pretty much every dress code you come across.
  • Lose the Velcro wallet. You may not have a big budget at this age, but you should upgrade to a leather wallet. It’s a small part of your overall look, but a youthful wallet can sink your other attempts to appear more mature. A quality wallet, though a big investment, should last you for the next decade.
  • Reserve your Nikes for the gym. When it comes to shoes, athletic shoes will absolutely make you look younger. Even if you still like to wear casual sneakers on the weekend, separate your gym shoes from your casual shoes. Upgrade your non-gym casual shoes to look at least a bit more formal than trainers, such as boat shoes or clean, simple leather sneakers.
  • Upgrade to classic hats. Sure, a baseball cap has it’s uses, but start thinking of hats as a way to accentuate your style rather than hide your bedhead. Try a flat cap. It adds a touch of maturity to your outfit, and your teachers won’t get mad at you if they catch you wearing it in the hall. Reserve the ball cap for the most casual and athletic pursuits. Wear it front facing with the bill curved, and the stickers and tags left where they belong: in the trash.
  • Buy a messenger bag, and throw out your college backpack. A backpack will immediately make you look youthful, so it’s time to give it to your little brother and upgrade to a messenger bag. Even if it’s made from the same material as your backpack, it’s a step up in maturity.
  • Start building a dress shoe collection. Be sure to read our article on the top three pairs you need. For casual shoes, there are also many options, so start looking for ones you like.
Alain Delon smoking in Rome 1969

Classic Style Icon of This Age

Alain Delon

When he first started making films, French actor Alain Delon was hailed as “the most beautiful man alive.” Embracing his youthful appearance, Delon favored simple and drapey clothing that emphasized his good figure without drawing undo attention to it. Rather than layering on bold items to attract every eye or squeeze himself into skin-tight clothing, he took advantage of the natural positive points of his age with clothing that allowed him, and his personal look, to speak for itself.

Dressing Your Age: Mid-Twenties to Late Thirties

Leverage Your Cachet While Enjoying Relative Youth

Illustration of 1930s outfits
Plenty of exciting new style oppurtunities await you as leave your youthful years behind!

Upon leaving your 20s and entering your 30s, you’re likely settling down. You have real bills to pay and mature relationships in your life. You’re working hard on your life goals, and you’re getting some traction. You’re maturing, and it may be tough, but you like it because your dad thinks of you as an equal, rather than lecturing you for having your shirt untucked. Even though you may have established your style by now, it’s still important keep evolving and considering how your style should serve your goals.

Tips for Dressing Well in Your Mid-Twenties to Late Thirties

  • Reevaluate your entire closet. In your thirties, you probably have some things in your closet that have been there since your teens or early 20s. Before starting, revisit the questions above, and then start editing. Note where you have gaps and garments that are just ok, and mark them for replacement. Throw away or donate clothes that no longer fit.
  • Start ordering custom shirts. By now, you’re probably tired of the shortcomings of OTR dress shirts. They just…aren’t quite right. Get yourself measured and start experimenting with custom dress shirts. Once you land on a great fit, you’ll probably never buy another shirt at the store again.
  • Add pops of bold colors to show you’re still young. A salmon v-neck in the summer or Go-To-Hell pants on the golf course will show you’re not settling for just the basics.
  • Kid-proof your wardrobe with our guide on clothing tips for dads.
  • Buy some classic sunglasses. You are now past the age when you can wear a latest sunglass fad, so it’s time to look for some sunglasses that won’t be out of style in 2 years. Consider Persols, Aviators, Clubmasters, or classic round frames. And please, only wear athletic sunglasses when exercising – it’s weird seeing a grown man wear Oakleys at brunch.
  • Bring your shoe collection to the next level. Once you’ve got the necessary three pairs of dress shoes, add more unique pairs in dyed leathers or with broguing for a more rakish look.
  • Start investing in higher-quality clothes. At this age, you’re probably feeling a bit more financially secure, so now is the time to start investing in higher-quality pieces in your wardrobe. We highly recommend buying quality outerwear, which can be enjoyed for decades if classicly styled and well cared for. Consider a Chesterfield, a Harrington jacket, a Burberry trench coat, a Covert coat, or a paletot coat.
  • Up your neckwear game. Consider some bow ties and neck ties when dressing in casual attire. Both work well with v-neck sweaters and cardigans. You can also add unexpected, Old World panache with ascots or scarves.
  • Challenge yourself to make new combinations. As you begin to get older, it’s easy to put on what you know that works. From time to time, make the effort to put together a new combination of elements to keep the skill alive.

Marcello Mastroianni had been acting since he was 14, but it was not until he reached his mid- and late thirties that he attained international acclaim. Perhaps this was because Mastroianni understand how to leverage his appeal at the critical intersection of time between being a young man and a more mature man: the oft-dread “middle age.” Mastroianni embraced this period, emphasizing in his style the liminal dichotomy between playful, youthful vigor and sedate, seasoned maturity.

Marcello Mastroianni

Classic style icon of this age

Marcello Mastroianni

Marcello Mastroianni had been acting since he was 14, but it was not until he reached his mid- and late thirties that he attained international acclaim. Perhaps this was because Mastroianni understand how to utilize his appeal at the critical intersection of time between being a young man and a more mature man: the oft-dread “middle age.” Mastroianni embraced this period, emphasizing in his style the liminal dichotomy between playful, youthful vigor and sedate, seasoned maturity.

Dressing Your Age: Forty to Sixty

You’ve Learned from Experience, Dress Accordingly!

Illustration of Various suits overcoat from Apparel Arts fabric display patterns
Just because you’re getting older, it doesn’t mean that you’re getting less stylish!

It is critical to remember that in your 40s, 50s, and 60s, you are, relatively speaking, still young, but with all of the benefits of being a mature adult. You’re working on your life goals, and you’ve known for a long time what works for your body and what doesn’t. You’ve got some favorites in your closet as you’ve invested in classics over the last few decades.

A photograph of Cary Grant

“There’s no point in being unhappy about growing older. Just think of the millions who have been denied the privilege.”

Cary Grant

Dressing at this age can be on auto-pilot, but times have changed and so should your look. Ageism in the workplace is real, with 21% of those over the age of 40 reporting falling victim to it, even though the median age of the US workforce is 42.2. Even though it should be incumbent upon the workplace to combat age discrimination, keeping your look fresh is one way you can affect how people perceive you.

Learn how to dress well over 40 from David Evans, the Grey Fox

Tips for Dressing Well from Forty to Sixty

  • Slim down the fit of most of your garments. While we don’t advocate chasing trends at any age, taking into account some of the macro level trends of the day will help you keep your look youthful. At the moment, slim cuts are in, so wearing a slim – not tight! – cut on your jackets, pants, and sweaters will immediately update your look.
  • Toss or alter garments that no longer fit you. In the ’80s and ’90s, workwear was much looser, and by today’s standards, they look oversized. Tailor any puddling pants to have no break or a slight break; pleats may be your thing, but toss or donate any pants that are too generous around the seat and thighs. If the shoulder seams of your jackets hang over the edge of your shoulder, add those to the pile too.
  • Update your glasses. Glasses have a unique power to make you look both mature and youthful when done right. If you’ve been wearing the same frames for 5+ years, it’s time to update them!
  • Update your dress shirts. There is no need to go out and buy a new rack of dress shirts in bold florals, but if you are relying heavily on classic white and blue, updating your shirts to add some small patterns like checks will add freshness to your look.
  • Avoid the “old guy” office uniform. If you work for a big company, there is probably a contingency of men between 40 and 65 that wear the company “uniform” every day. Try something new but still work-appropriate.
  • Keep your denim recent. Denim is particularly unforgiving when it comes to looking dated, so try to update your denim regularly at this age. That means NOT buying the same brand, wash, and cut every time you shop, nor does it mean you have to buy ripped, whiskered jeans with embroidered pockets. For a classic look, invest in dark wash denim that’s been properly hemmed (or pin-rolled)
  • Reevaluate your neckwear. Like with other aspects of your wardrobe, neckwear like ties and bow ties can age poorly. It’s time to consign or donate your 80’s and 90’s ties and add some stripes, neats, and bow ties in classic patterns and widths. While you’re at it, double check if you need a short or a tall tie; they weren’t widely available 20 years ago but sizing is great for solving the issue of the too-long or too-short tie.
  • Freshen up your haircut. This could be a tough one; at this age, you probably know exactly what you like and what looks good on you. Even though you might not have changed your hair in a decade, we highly recommend giving it a go; it’s a crucial part of having a youthful aesthetic. If you wear a classic side part, for example, consider shortening the sides. Even if your hair is thinning, you can try many excellent Classic hairstyles.
  • Use color carefully, but don’t avoid it. Chatreuse sports jackets should be a thing of the past for you, but color is still your friend. Employ classics like pastels in summer and jewel tones in the colder months. Use bold colors as an accent in accessories and you can’t go wrong.
  • Don’t give in to the temptation to go the “comfort” shoe route if you don’t need to. We understand that feet have their own needs, but when it comes to footwear, dressier styles will make you look more polished and youthful than obviously youthful styles. So skip the Vans and look for loafers, mocs, chukkas, and pretty much any other boot. Boat shoes work well in the summer, but sneakers are best left for the gym.
  • Find a style role model. Sometimes it’s hard to pin down what youthful but mature looks like…exactly. If you’re struggling to do it just from this list, find a guy out there who’s style you like, and find ways to model your style after theirs.
  • Finally, try something new. Even though you’ve gone through all the steps above, it never hurts to try something new, especially at an age when you could probably change nothing and still be fine. The point is, practice using your change “muscle” by getting out there and trying something new. How about a leather jacket, a richly colored shoe, or a summer blazer?
Cary Grant wearing an ascot in To Catch A Thief

Classic Style Icon of this age

Cary Grant

Few men aged as well as Cary Grant did. With a film career spanning decades, Grant managed to stay just as attractive in the 1960s as he had been in the 1930s. He achieved this by carefully and thoughtfully planning every aspect of his ensembles for maximum appeal. Looking good as you age may require a bit more work and attention to detail, but as Cary Grant shows, that hard work will definitely pay off.

Avoid these style mistakes that make you look older!

Dressing Your Age: Sixty and Older

Fully Enjoy Your Golden Years with Style

Illustration of a younger man and older man in summer suits
Don’t forget to pass on a few of the style secrets you learned as you aged to the next generation!

At this age, you’re likely retired or looking forward to it…or maybe you never want to retire at all! You spend your days on the golf course, playing cards with friends, or traveling the world. Just because you’re getting older doesn’t mean you need to trade in the Oxfords for Velcro shoes! You can still look your age and remain fashionable and comfortable at the same time, but the goal is to avoid falling into certain traps. Start by reviewing the age 40-60 category above – all those suggestions are still relevant for you. Here are a few extra tips to consider as you celebrate a few more birthdays.

Frank Sinatra With Collar Pin

“You only go around once, but if you play your cards right, once is enough”

Frank Sinatra

Tips for Dressing Well When Over Sixty

  • Don’t overcompensate – it’s obvious and unflattering. Overcompensating for your genetic luck, like covering up thinning or graying hair, can make those features even more painfully obvious. It is usually much better to be a confident bald guy who owns it rather than imply that you’re embarrassed about your age by hiding it. Embrace the hair you have, whatever color it may be!
  • Care less about what other people think! Congrats, you’ve made it through the bulk of your career, and now it’s time to reap the rewards. One of those rewards is the right to care less about what other people think. We still recommend dressing appropriately for major occasions such as weddings, funerals, board meetings, and the like, but when you feel like doing things your way, go for it, because you’ve earned it!
  • Reevaluate your shoe needs. As you age, your feet and their needs will change. For some men, stiff Goodyear welted shoes may no longer be comfortable. Instead, look at orthotics that can be placed inside the shoes, rather than buying orthotic shoes, or opt for shoes with less structure, such as loafers or Chukka boots.
  • Edit your wardrobe every five years, and change it as your body changes. As we age, our bodies change, and wearing well-fitting clothing is always a good look.
  • Keep your accessories simple and classic. A plain gold watch like a Cartier Tank will look sleek and sophisticated, especially paired with simple gold cuff links or a matching collar bar.
  • Don’t be afraid of layering. If you find that you get colder faster, layering is the best way to ensure you always remain comfortable. Keep your layers slim fitting, and the look will still be fresh.
  • Keep investing. Even though you may think you have a complete wardrobe, it’s important to keep refreshing your collection as things wear out, go out of style, or no longer have a use for you. Don’t forget to add new and different garments as well!
Illustration of older men in youthful styled 1960s outfits
Sometimes, more youthful-appearing clothing can help you feel younger!
Dr. Andre Churchwell with Panama hat, and striped suit other accessories

Classic Style Icon of This Age

Dr. Andre Churchwell

Few older men are better known for their exceptional personal style than Dr. Andre Churchwell. Bold, brilliant, and beautiful, Dr. Churchwell’s ensembles exude dandy panache but with a dignity befitting his age and status. This balance is achieved by relying on Classic Style conventions to guide every outfit while remaining true to Dr. Churchwell’s personal spirit and comfort: it is clear that every ensemble is genuine and nothing is affected. The results are wonderfully distinctive looks that, while they could work on a younger man, appear truly perfect on Dr. Churchwell.

Conclusion

There are many ways to look younger or older, depending on what you’re trying to achieve. For most of us, the goal isn’t that, but more so to just look our age. We hope that the secrets we have shared in this guide will help you look your very best, no matter what your age!

What tips do you have for dressing your age?

Outfit Rundown

Raphael in an office- and age-appropriate ensemble.
Raphael in an office- and age-appropriate ensemble.
Two-Tone Knit Tie in Red and Navy Blue Changeant Silk - Fort Belvedere

Fort Belvedere

Two-Tone Knit Tie in Red and Navy Blue Changeant Silk

Purple Carnation Silk Boutonniere Buttonhole Flower

Fort Belvedere

Purple Carnation Silk Boutonniere Buttonhole Flower

Pale Yellow Linen Pocket Square with Yellow Handrolled X Stitch - Fort Belvedere

Fort Belvedere

Pale Yellow Linen Pocket Square with Yellow Handrolled X-Stitch

Monkey Fist Knot Cufflinks - Vermeil Sterling Silver Yellow Gold Plated

Fort Belvedere

Monkey Fist Knot Cufflinks – Vermeil Sterling Silver Yellow Gold Plated

Grey Socks with Light Grey and Black Clocks in Cotton - Fort Belvedere

Fort Belvedere

Grey Socks with Light Grey and Black Clocks in Cotton

Today Raphael is wearing a blazer taken from a navy blue suit. It’s double-breasted, has a faint windowpane, and is from Ralph Lauren Purple Label, via eBay. He pairs it with an unusual striped shirt in yellow and a dark stripe to add a little more boldness to the ensemble. He has a two-tone red and navy silk knit tie from Fort Belvedere, which he pairs with a yellow linen pocket square with yellow X-stitches from Fort Belvedere. Note how well this slight contrast highlights the stripes of his shirt.

Raphael’s boutonniere is a dark purple-pinkish carnation that goes well with his tie. His pants are custom-tailored in a sharkskin mid-gray fabric with inverted double pleats to accommodate Raphael’s larger thighs and posterior. His trousers have cuffs, also called “turn-ups,” because, in a lightweight fabric like the one he is wearing, cuffs help hold the pant leg down for a clean and elegant break that does not ride up.

Raphael’s grey socks with grey and black clock detailing are great for a little bit of contrast to the pants, and the clock design creates visual interest while remaining office-appropriate. He pairs them with black semi-brogue Oxfords.

The cufflinks Raphael is wearing are Gold Monkey Fist cufflinks from Fort Belvedere. They’re very timeless, and Raphael personally designed them because he never liked the silk knots that were available, but he liked the nautical theme. He wears a ring in 14-karat yellow gold that matches his cufflinks and features a citrine stone. He acquired it from a vintage flea market in Boston.

Overall it’s a very classic office outfit; however, because of his colorful shirt and tie, it appears considerably more youthful than if he were to wear the same thing with a striped red tie and a light blue shirt, or perhaps a white shirt. Those options would, in turn, appear more professional.

Reader Comments

  1. Thank you, for a very, very necessary article about being a Man, regardless of the life-season. I shall show this to my catastrophic friends (wife, children, sedan) and remind them that adulthood is better than superannuated adolescence.

    1. I agree with your great advice. I have Instagram babyboomersstylings to show how I dress at age 62 and now 63. Our age group knows better than anyone else how we dress out of respect for people we encounter that day. As the old rule applies as well, first impression offers itself only one time period. Keep the articles coming. Great job!

  2. I found this article both beguiling and irritating to read. While I agree implicitly that men in their 30’s … actually no man, period, should wear pants that sag & show their unmentionables, it is clear that Throughout this article there is a overt tone of ageism. The author is giving advice based upon his own belief systems of what’s what and what one should wear. True men’s fashion is what one wears one’s self with confidence, not what GQ tells you to wear in a photographed curated outfit on page 4. Ridiculous. Beau Brummel was his own man, women wanted him and men wanted to be him. If you want to play it safe & suppress what makes you feel good ( but what may not be in the “rules”) then this is a great article for you. Just remember; The man makes the clothes, the clothes do not the man make. The picture of the older more mature dapper gentleman as an example of dressing “too young” was a fail. I thought he looked great, and what’s more, one would have to see how he wears his clothes. What’s attractive to people aren’t the clothes, it’s confidence. The illusion people have, is wearing a suit and ‘feeling good’. Wearing a certain style that gives off a certain ‘command’ & it makes them ‘feel’ good. How many times have we seen a classless cad in a well tailored suit, I ask you? Or you see a gent very well dressed, and it’s clear that much of it is affectation because there’s no real confidence in what one wears. When one feels the confidence of being a gentleman, having integrity, having benevolence… People. Will. Notice. The clothes are only a footnote. I’ve seen plenty of handsome ‘dads’ with their children here on the streets of NY dressed in the same way you warned NOT to dress if you’re not early twenties. The key here, is balance. The photo of the mature gentleman is perfect, I might lower the hem in his jeans because for me, high water pants destroy the silhouette of a gent. For the younger photos, I might tell a dad to replace the pants with pants that fit and don’t sag, keep the rest(hat too) and wear a nice blazer. The point here is; ill fitted clothing does not flatter anyone no, matter the age. (High water pants, or baggy joggers on a young or mature man). Follow your instinct, and make sure your clothes fit proper. And remember chaps ; The man makes the clothes, the clothes do not the man make.

  3. In seriousness, would a pinstripe gray or navy qualify – or should it be solid for a first suit?

  4. “Perhaps you spend weekends golfing or sailing in the summer.” This smacks of the “17 Careers for Stylish Gents” article. I think men of any status and income can be stylish, but not all can afford these types of hobbies, even when in their 40s. I’m sorry.

    And why should a gentleman over 40 avoid pink. Many men, some into their 60s, wear pink dress shirt and it looks great.

    To me “dress shirts” are shirts to be worn with a tie. When going tieless a button down collar shirt (which may be an OCBD or “sport shirt”) is much better.

    Finally, that example of shoes to add a youthful touch…I don’t see many youths wearing shoes like that, so I don’t really understand the suggestion. Not particularly good looking shoes, IMHO.

  5. Thank you for a valuable guideline and insight to dressing sensibly for my age, 65+.
    Since being influenced by Carnaby Street fashion in the mid sixties it’s been a real passion to always retain, just a tiny sprinkling of style.
    A dash of style always takes the monotony out of something we must do every day of our lives.

  6. Delar Sir. You didnt mention the odd waist coat under the jacket. The cheapest way to ad style for the grown up man. Cost nothing in second hand shops.

  7. I am a 14 year old who wears suits and sport coat combinations to school. I have more ties than most adults do. I have a 1930-40s inspired style. I am doing thepolar opposite of dressing my age.

    1. Thats fine Robert. At school, a suit WAS our uniform so it felt natural. As a coda, I wore a blazer for rowing, but the tone was formal. My suggestion (at 61) is to wear what you like. Enjoy what you like and be yourself. You will wear it better than conforming to any rules.

  8. Nice article.

    Dress hats are also good for middle aged or. older gents. Good for hair loss or just looking stylish. That is real hats, not baseball caps….

  9. Being well dressed and stylish is important at all ages.. But it’s important that we all interpret our own style, once the basics are known.

  10. Pathetic attempt at pushing someone else’s views on others. If you look younger than you are then screw what this says. Older but fit and attractive gentlemen have more leeway with fashion and can get away with more. I am proof of this.
    But a suit makes them wet!

  11. Interesting tips… BUT. As always with something that is pronounced “classic” (clothes, cars, architecture…), there’s one question: where exactly is the cut-off point where anything new doesn’t count? Why is the preppy style that was born and evolved in the affluent student circles some decades ago considered good taste and the clothes popular among today’s campus crowd deemed universally bad? Sounds kind of snobbish. And let’s face it, some things, however classic they may be (like top hats), look hopelessly outdated.

    1. Classic is something that has evolved over time for specific reasons. Is it totally subjective? Absolutely!
      Some things are more flattering than others.

      In my experience, a nice outfit with a classic suit will earn you compliments no matter what country you visit.

      Of course, if societies decided to wear sleeves reaching our ankles and everyone said, that’s awesome, and the norm, then that would be it. And we would consider that classic.
      Even the fact that we wear clothes in areas around the equator at all, makes no sense if you think about it.

      At the end of the day, it is all about social norm. If you show a picture of someone in sweatpants, next to the same person in a suit, and you ask who earns more, who is more intelligent, who is more elegant, who is better dressed.
      Chances are more people will say the guy in the suit is.

  12. The photo of the older gentleman at the train station was probably intended to be humorous; but, actually, I think he makes it work!

  13. A most interesting read showing great points of view for the times in which . My only gripe here is the modern day use of the word ” kids ” to describe our glorious offspring . We humans produce children ; goats have kids , cats have kittens and faols have chicks and Old Macdonald had a farm.

  14. At the risk of committing Dandiacal blasphemy, IMHO, DiCoggiola is a master of costume, not style. He not only does NOT dress for his age, he doesn’t dress for this age. He looks like he obtained his wardrobe at Oscar Wilde’s estate sale.

  15. I live in a smaller city where on a Sunday summer morning at Costco, 95% of the men from 16-66 were all in cargo shorts and t-shirts. I was in khakis and a Navy Polo. I did almost run into one man in khaki shorts and a Polo. If I dress like that to go grocery shopping my wife has a fit. I still put on a tie once a week and visit my stores.

  16. I am unsure of the premise to this article. Most of the offerings have been very well reasoned and the article on Spectator shoes was very useful for me – I had a pair, hand made in Georgia – the country, rather than state a couple of weeks ago.
    Surely the point is to wear what feels right. i.e. if you feel right in what you wear, it will look right. I wear very classic tailored suits etc., my erstwhile colleague favoured avant-garde. Our tailor must have wondered how we were friends as our tastes differed so much, however, both of us felt good in what we wore, as it fitted our individual personalities. Having grown up with my (British) grandparents and having been to Prep and later Public (British = Private) school, wearing classics was the most natural thing in the world.
    My colleague was/is in a different mould, but thats fine. He is he and I am me. In a double-breasted suit quite possibly he would feel uncomfortable and vice-versa.

    Mostly your offerings are excellent and even on subjects I know, offer great insights into the more technical aspects that are useful.

  17. A well-rounded piece, deftly treading the tightrope of sartorial opinion, where virtually any suggestion can be opposed by independent opinion.

    I believe we (that is the more sartorial ‘we’) dress differently in order to find physical form for our self-expression: for some this is limited to our clothing, a few lucky ones can add lifestyle (classic cars, period houses, jetset lifestyle) and some commit heavily on improving the self (confidence development, public speaking and the like).

    I applaud this article for having the nerve to tackle such an emotive, wide-ranging and subjective topic.

    By engendering such a range of responses the article is the catalyst for gentlemanly discussion that clearly demonstrates a knowledgeable community enjoying a healthy and informed debate.

    To the critics of the article (apart from the obvious trolls) you are entitled to your opinions and I certainly agree with some: the joy is that we are having the debate at all!

    I am old enough to recall when only the super rich or the insane would be accepted as wearing anything other than the social norm of the time…

    Good health to you all.

  18. I always wear a sport coat or blazer when I board a plane, (I’m 75 so I’m old school), and I usually get upgraded to first, I think the flight attendants are happy to see someone dress up for a change. The “I’m with stupid tee shirt doesn’t cut it in first anymore

  19. Very thoughtful post. Men must dress up as per their age if not it will not be well received. In public places like hotels, parks, hospitals, when we see men above 50 with a t-shirt and jeans, we see it as odd. Thank you for the beautiful message.

  20. A very thoughtful post. Very true that men must dress according to their age. In public places like, parks, hotels, hospitals, when we see men above 50 with a t-shirt and jeans, we feel odd. Thank you for the beautiful message shared.

  21. This is the best mens fashion guide for all ages to look stylish and trendy with the latest trends. Fashion is not limited to age or size, it is for everyone.

  22. Please woman…im sure thatsbwho wrote thid bc they always disguise themselves when secretely changing the sppecies of man. Ever ponder such a thought to why women are pushing the idea of vegan? Think about it…1 of the things women have observed about men as overall we are larger and perhaps some of us…maybe all of us are stronger physically then women. (I said some) so if you slowly take away our strength and confidence then our species is slowly being captured and brought to bow before the feet of the woman who seek money power and emotional flares everywhere in between. Like screaming on the playgrounds as kids. Why do they always do that? Emotion and external internal bursting makes them feel noticed. Women…the moment you over come the male population the world will end. There will be no time to celebrate. Just stick to dressing yourself.

    The Captain

  23. It is likely that you have, at some point in your life, been told to “dress your age.” But what does that actually mean? In this guide, you will know how to dress appropriately for your age and why doing so can greatly benefit your personal style, confidence, and how others perceive you.

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