How to Dress Your Age: Balancing Style with Maturity


Dressing appropriately for your age – what exactly does that mean? In this guide, we’re going to explore how to dress appropriately for your age–and more importantly, for how you want to be perceived.

We’ve all seen men middle aged men dressed like teenagers, and the attention they are likely to receive isn’t positive. Dressing your age, as a concept, has always been around, and it assumes that there is a “right” way to dress at every age. But is that really true anymore?

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

Dressing Your Age: Does it Really Matter?

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.

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? Is it important to you to be perceived in a certain way?

For most men, that answer to that question is yes. In business, for example, wearing a Rolex watch can signify your success, and may make future clients more comfortable doing business with you – even if you don’t like Rolex. If you work in an office, a dress code might require you 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.

Dress Your Age, But Only if it Suits You

The exceptionally rakish Parisian dandy Massimiliano Mocchia Di Coggiola

Some men, especially our readers, are stylish gentlemen that offering suggestions on how to dress your age is like giving style advice to Massimiliano Mocchia Di Coggiola. These men have the unique ability to dress in a style all their own, regardless of their age and regardless of how other perceive them. They’ve decided what they like and they want to only wear that! That doesn’t work for everyone. For the rest of us, here is some food for thought regarding dressing your age.

Sven Raphael Schneider, in a seersucker suit and white brogues, knows that style knows no age

Start by Asking Yourself These Questions:

How do I want people to perceive me?

As older, younger, my age, successful, arty, etc? Make this your primary consideration when choosing what to wear.

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?

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?

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?

Young Men Under 25

If you’re past the age where your mom picks out your clothes, you finally have the chance to shape your own style and wardrobe. 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.

Short Tie 1930s style by Ethan Wong, the Teenage Gentleman

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 don’t need to throw on a jacket and tie. Instead, here are some tips to successfully mixing youth with maturity-boosting style.

This look works for teenagers or early twenties, but anything older will make you look like you’re trying too hard

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 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.

Early- to Mid-Twenties

Our Content Director and YouTube host, Preston, is in his mid-twenties

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.

A great business casual outfit minus the sunglasses

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:

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 regularly 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 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 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 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.

Mid-Twenties to Late Thirties

Sven Raphael Schneider in green Baracuta G9 Harrington Jacket with Chino

At this age, 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.

Tanner Guzy from Masculine Style and Sven Raphael Schneider from Gentleman’s Gazette

Reevaluate your entire closet. At this age, you probably have some things in your closet that have been there since your teens or early 20’s. 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 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 peices 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.

Challenge yourself to make new combinations. As you begin to get older, it’s easy to put on what you know what works. From time to time, make the effort to put together a new combination of elements to keep the skill alive.

Forty to Sixty

You’re still young, but you’re 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. 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.

A Portrait of the Grey Fox, David Evans

For more insights into dressing over 40, be sure to check out our in-depth interview with David Evans from the Grey Fox.

Jason Statham looking confident even without a full head of hair

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 80’s and 90’s, 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. It’s no surprise

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” everyday.

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 pinrolled)

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. If you’re not sure what to do, ask your stylist, or (eek!) find a new one to make suggestions.

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?

Sixty and Older

Dr. Churchwell in light gray flannel suit

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 once you’re a cadidate for Medicare:

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

Don’t overcompensate – it’s obvious and unflattering. I doubt very much that people look at Donald Trump’s hair and wish they, too, looked like that. Overcompensating for you genetic luck usually ends it being even more painfully obvious that it was before! Much better to be a hip bald guy who owns it than an looking desperate and insecure. 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, etc,

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 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!

Lino & Co don’t let age factor into their love of style


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.

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