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.
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.
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.
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.
- 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.
- 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.
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.
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.
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.
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 without being over the top. A 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.
Tips for Staying Young
- Use bold colors and patterns to accentuate your youthfulness.
- Wear chinos, denim jeans, and cords with casual attire.
- Walking sneakers, driving mocs and boat shoes are perfect for the summer.
- Use bolder accessories like socks, neckwear and pocket squares to accentuate outfits.
- Sweaters such as cardigans with collars and zip-up sweaters will take years off your look.
- Consider D-ring belts, rope belts, and other casual belts to appear more youthful.
- Leave shirts untucked to look younger. Consider polos, button downs, and sailing shirts.
Tips for Looking More Mature
- Add layers using v-neck sweaters in monochromatic colors.
- Avoid bold colors and stick with classics like navy and gray.
- Opt for dress shirts instead of button-downs or casual shirts.
- A dressier belt on a casual outfit will add maturity.
Consider tassel loafers your go-to casual shoe.
- Simple, understated, yet elegant accessories in yellow gold add maturity every time.
- Hats like the Homburg, trilby, flat cap and fedora add a touch of elegance.
- Choose bow ties over neck ties and wear them casually as well as with business attire.
- 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.