How to dress your age

How to Dress Your Age

In this guide, we’re going to discuss how to dress appropriately for your age and transition into the next stage of your life effortlessly without being noticed.

We’ve all seen the middle-aged man wearing oversized track pants hanging from his hips and a jersey that looks like he borrowed it from his dad. We know we saw this kind of man because he stood out to us. We noticed him. And it wasn’t for a positive reason.

George Clooney happy to look his age with salt and pepper hair

George Clooney happy to look his age with salt and pepper hair

Why It’s Important

The fact is that the saying “you’re only as old as you feel” really doesn’t apply to your appearance. Because unless you’re willing to wear a sign that says “I feel 20”, most people will look at the salt and pepper hair and crows feet and be able to guess your approximate age in seconds. It’s nothing to be ashamed of. You earned those crows feet. They’re not wrinkles; they’re battle scars like a tiger’s stripes that show you’ve taken life by the horns.

No one ever looked at George Clooney or Richard Gere and said: “Wow, that gray hair looks terrible.”

But, we can easily argue that if Clooney or Gere wore the clothes that Justin Bieber or another teen pop star wore we’d likely scratch them off our list of well-dressed men.

The exceptionally rakish Parisian dandy Massimiliano Mocchia Di Coggiola

The exceptionally rakish Parisian dandy Massimiliano Mocchia Di Coggiola

Dress Your Age, But Only if it Suits You

Some men, especially our readers, are such rakish gentlemen that offering suggestions on how to dress your age is like giving style advice to Massimiliano Mocchia Di Coggiola. It makes no sense.

Some men have the unique ability to dress in a style all their own, regardless of their age. This article is for the rest of us. After all, we cannot break the rules until we’ve mastered them.

This look works fine for teenagers or early twenties but nothing later

This look works fine for teenagers or early twenties but nothing later

Under Twenty

If you’re past the age where your mom picks out your clothes, but you’re not quite out of high school yet, you can pretty well get away with a sloppy dressed down grunge look or a bow tie. You’ve got some options. However, if style is important to you, then chances are the only time those sweat pants come out is in gym class or on game nights at home while playing Call of Duty with your bros.

If you want to maintain a youthful appearance but dress better than your friends, focus on casual layering. Unless you’re going to a job interview, a wedding or a funeral, you don’t need to throw on a jacket and tie. Instead, here are some tips to make you the best-dressed guy at school.

Tom Selleck with chest hair protruding from his shirt

Tom Selleck with chest hair protruding from his shirt

  • Stick with chinos over denim jeans, or cords in the fall and winter. Slim but not skinny trousers are your friend and separate you from the masses. Colors like burgundy, navy, and stone will work well for you and give a youthful hip appearance, but still be professional enough for that part-time job delivering pizza on the weekends in your mom’s Volvo.
  • Button down shirts are your friend. Particularly in checks, plaids, and stripes. Leave the top button undone or go West Coast prep with Johnnie Oh’s tweener shirts that let you go unbuttoned without looking like a 1970’s Tom Selleck. Don’t get too bold, but feel free to add pops of color.
  • Take off the ball cap and put on 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.
An older man wearing baggy and sagging jeans

An older man wearing baggy and sagging jeans

  • Add sweaters to layer colors which adds some texture to your still-teen physique that will pass off as muscle. Solid v-necks over your button-down or even a Henley will work well. Colors like olive green, navy and burgundy work well, and thinner Merino wool sweaters look more youthful. For a preppy look, consider a thicker lambswool knit sweater with a shawl collar and toggles instead of buttons. It will add a touch of class and definitely win points for prom king.
  • When it comes to shoes, lose the Nike’ and consider a pair of Chukka boots or casual walking sneakers from Sperry Top-Sider. They’re just as comfortable but far more stylish than running shoes which should be reserved for athletics only.
  • As far as watches and jewelry goes, feel free to throw on the Fossil or Nixon, but make sure it’s not ridiculously huge. A watch that’s under 42mm will look better and ideally you want something 40mm or smaller. If you want to wear something more youthful, consider a chronograph or sports watch, even if you’ll never use it.
Bold flat cap is ideal for young men

Bold flat cap is ideal for young men

Early to Mid Twenties

You’re either in college or getting that first big job: the career as your father will call it. 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:

  • 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 gray. Something simple that doesn’t have a pattern to it. That way if it is your only suit, people won’t be able to discern that quickly. Patterns are easily remembered, so unless you’ve already built up a collection, leave the windowpane at the store. 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.
  • For casual wear, leave the jeans for the workshop. Instead, go with the chinos, dress trousers, and other casual slacks. There’s a broad range on the market, so get creative. Make sure you focus on fit and quality.
  • It’s time to grow up and lose the velcro wallet. Buy a gentleman’s wallet. A high-quality one that will last your lifetime. Pick up a good watch. It doesn’t have to be a Rolex, but leave the Nixon and Fossil at school. Focus on a classic dress watch if you’ll only wear one and make sure it can alternate between black and brown leather bands. That or start to collect.
  • If you still like the old band t-shirts you wore while playing the drums in your parent’s garage; you can still get away with them. For now. But wear them ironically. Pair them with stylishly washed jeans or contrasting chinos. Add a zip-up sweater over top without a hood and mostly unzipped. You’re young still and if you have kids, you’ll be the cool dad on the block. Just keep in mind that only lasts until you’re about 28 or 29. Then it’s time to retire the band shirts and use them as rags as you desperately try to restore the Camaro you drove back in high school. Some things just belong in the past.
  • When it comes to shoes, now is the time to buy some dress shoes. Be sure to read our article on the top three pairs you need. For casual shoes, there are also many options. Just avoid the Converse, Sketchers and other brands you see the young whippersnapper’s wearing these days. You’re not in high school anymore.
Dressing too young for your age can often have the wrong effect

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

Mid Twenties to Late Thirties

You’re likely settling down. Maybe you’re still dating, or you’ve met the one. You may even have a kid or two. You’ve moved out of the dorms; you’re either in an apartment you’re kind of proud of, with a liquor cabinet that has more than just cheap beer and Schnapps in it. That or maybe you bought your first house. You’re in the suburbs, and you likely drive a car that doesn’t wake up the neighborhood when you pop it in drive. 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. Here are some tips to transition into the mature suburbanite you’re slowly becoming.

  • The button down is still great. If it’s reserved for weekend barbecues and block parties. Start focusing on dress shirts now. Polos can be worn with shorts on the golf course and dress shirts paired with sweaters, suits or by themselves.
  • Focus on textural components in your clothing rather than visual. Avoid the bold colors you once wore and instead add pops of sprezzatura with knit ties or a Grenadine tie that works perfectly with most of your jackets. Opt for a blazer over a sweater and add a repp tie to show you’re still young. If you work in an office, suits are your friend. Build up a collection of the basics and add blazers and patterns to compliment the base collection.
  • 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 can still hang out with the guys.
  • If you have kids, be sure to read our feature on clothing tips for dads.
  • Begin to build that shoe collection. Once you’ve got the necessary three dress shoes, feel free to add more unique pairs in dyed leathers or with broguing for a more rakish look.
  • The same sweaters and chinos work, but now is the time to add charcoal and other gray sweaters to the collection.
  • Consider some bow ties and neck ties when dressing in casual attire. Both work well with v-neck sweaters and cardigans.
  • In the summer, consider sailing shirts like the ones from Saint James which add an air of sophistication to an otherwise casual outfit. Paired with boat shoes or driving mocs, you’ll be the most dapper dad on the boardwalk.
Ben Affleck looking mature and yet still young with his kids

Ben Affleck looking mature and yet still young with his kids

Forty to Sixty-Five

You’re still young. There’s no denying it. You go to work every day. You likely hit the gym a few times a week for a tennis match or a swim. Perhaps you spend weekends golfing or sailing in the summer. You’re the most comfortable age there is. You’ve got the house, the car, a family. Or, you live the life you want to live and are hopefully very happy with it. Be sure to check out our in-depth interview with David Evans from the Grey Fox.

The clothing doesn’t change drastically, but it becomes slightly more reserved. Here are our tips:

  • Avoid the bold colors like pink, bright green and lilac. Instead, focus on the classics like gray and navy. Use patterns instead of colors to accentuate your look. A bright pop of a red pocket square in the breast of a light gray double-breasted suit will pair sublimely with an equally sophisticated – and yet dashing – tie.
  • Consider odd combinations. Leave the gray trousers at home and wear your suit jacket with navy dress pants.
  • Add tweeds to your winter and fall wardrobe. Whether it be a tweed flat cap or a jacket, it will showcase your maturity and stability as a gentleman who is comfortable looking his age.
  • Avoid layering with sweaters. It looks great on younger guys or older guys, but it can age you quickly if you don’t do it well.
  • Use bright socks or a bolder pattern in your pocket square to add some youthfulness to your appearance. Just make sure it’s not over the top.
  • Stick with classic colors for your casual wardrobe as well. A navy, burgundy or even a white polo shirt will be far more stylish than a rugby polo shirt.
  • If you enjoy adding color to your outfits, consider burnt orange, dark purples, olive greens to enhance your look.
  • When it comes to casual footwear, look at loafers and mocs. Boat shoes work well in the summer, but sneakers are best left for the gym.
Richard Gere has long been considered a sex symbol due to his salt and pepper hair

Richard Gere has long been considered a sex symbol due to his salt and pepper hair

Sixty-Five and Up

You’re likely retired or looking forward to it. Perhaps you’re a snow bird and go away for the winters. You spend your days on the golf course, playing cards with friends, or perhaps you volunteer. Of course, many who grew to love their profession may still work as long as possible. 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. Here’s how:

  • Now is the time to add sweaters back under your blazer. It will match your age well but also keep you warm and comfortable if the temperature drops. If you get too warm, just take off the jacket. A forest green v-neck under tweed often looks dashing. Think British Country style.
  • Shoes need to be more comfortable, but you can still have fun. Instead, look at orthotics that can be placed inside the shoes, rather than buying orthotic shoes.
  • If you require assistance walking, leave the plain brown cane and tennis balls at Walmart. Check out places like ElderLuxe for stylish walking sticks that look, but aren’t more fashionable than functional.
  • Dress pants may be more comfortable than the weight of chinos or cords. And they look good whether you pair them with a jacket or just a sweater.
  • Consider vertical striped shirts that elongate your body. This becomes especially helpful as we get older and begin to hunch over slightly.
  • Make your accessories more versatile. A plain gold watch like a Cartier Tank will look effortlessly stylish and commanding without being over the top. A signet ring can also enhance your style.
  • Avoid the bold patterns in neckwear. Instead add sprezzatura with a boutonniere, fine peccary leather gloves in the winter, or a lovely cashmere or alpaca scarf.
  • Don’t be afraid of layering. If you find you get colder faster, layering is the best way to ensure you always remain comfortable.
  • Lighter casual trousers will make you look younger but not immature. White trousers in the summer or a pale blue for a pop. You can also stick with stone, creams, and beige.
  • If comfort is an issue, reserve suits for important functions. Instead, wear softer and less restrictive apparel. A smoking jacket or a sack sports jacket that’s fuller through the chest may offer more comfort than a well-fitted business suit.
  • Shoes are another way to emphasize style. Consider wingtips, brogues and even multicolored dress shoes to add style to your outfit. You can also use bold fashion socks.
Dont dress like your kids

Dont dress like your kids

Tips for Staying Young

  1. Use bold colors and patterns to accentuate your youthfulness.
  2. Wear chinos, denim jeans, and cords with casual attire.
  3. Walking sneakers, driving mocs and boat shoes are perfect for the summer.
  4. Use bolder accessories like socks, neckwear and pocket squares to accentuate outfits.
  5. Sweaters such as cardigans with collars and zip-up sweaters will take years off your look.
  6. Consider D-ring belts, rope belts, and other casual belts to appear more youthful.
  7. Leave shirts untucked to look younger. Consider polos, button downs, and sailing shirts.
A perfect way to add youth for an older gentleman

A perfect way to add youth for an older gentleman

Tips for Looking More Mature

  1. Add layers using v-neck sweaters in monochromatic colors.
  2. Avoid bold colors and stick with classics like navy and gray.
  3. Opt for dress shirts instead of button-downs or casual shirts.
  4. A dressier belt on a casual outfit will add maturity.
    Consider tassel loafers your go-to casual shoe.
  5. Simple, understated, yet elegant accessories in yellow gold add maturity every time.
  6. Hats like the Homburg, trilby, flat cap and fedora add a touch of elegance.
  7. Choose bow ties over neck ties and wear them casually as well as with business attire.
  8. A double-breasted jacket with peak lapels will look rakish and mature at the same time.


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. What tips do you have for dressing your age? Be sure to send us a picture in your favorite outfit.

How to Dress Your Age
Article Name
How to Dress Your Age
The ultimate guide on how to dress your age from the teen years to senior years with tips and tricks to dressing young and adding maturity.
Gentleman's Gazette
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28 replies
  1. Mariano Torrespico Ortíz says:

    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.

    • Manuel Ramirez says:

      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. Sir DySart says:

    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. Tom says:

    “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.

  4. Michael says:

    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.

  5. Robert says:

    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.

    • Harvey Pincis says:

      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.

  6. Simon says:

    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….

  7. Tom says:

    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.

  8. Alan says:

    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!

  9. Andrew says:

    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.

    • Sven Raphael Schneider says:

      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.

  10. Lowell Davis says:

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

  11. Mark in OZ says:

    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.

  12. W. Mandelbaum Esq. says:

    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.

  13. Ran23 says:

    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.

  14. Harvey Pincis says:

    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.

  15. The Earl of Flinders says:

    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.

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