How to Dress for Your Age

Society always stresses that we must dress our age, but how can we even be sure what that means?

When we’re young, we’re always told to dress more professionally; older men are bombarded with marketing showing mainly men in their twenties.

Thankfully, it isn’t tricky to stay age-appropriate as long as you know some fashion fundamentals.

Why Dressing for Your Age Matters

It may be unfair, but people make up their minds about you almost as soon as they meet you. So your first impression is everything and dictates how future interactions will go.

How you dress says tons about you. Dressing appropriately confirms to people that you take yourself seriously and are capable and competent.

Also, it’s important to dress well in a style appropriate to your age. That’s a quick way to demonstrate you are where you should be in life and have the experience to understand how things work.

You don’t want to misrepresent yourself. If you dress too young for your age group, people may decide you look foolish; dress too old, and they may worry that you’re pretentious.

As you age, your appearance naturally morphs. Unfortunately, not all styles work with each stage, so it’s vital that you alter your wardrobe each decade.

How to Dress Your Age in Your Twenties

Ah, your twenties. This is a time when you can get away with nearly any style; practically everything looks good on you!

Still, it’s critical to set your tone with your clothing. You are discovering who you are and experimenting with much in your life.

That should include your style. Your twenties are a time to build up your wardrobe and invest in a few long-term pieces.

Introduction to Suits and Formalwear

Although it’s natural to dress in the more trendy styles of the day in your twenties, you should stick with traditional styles for suits.

While I understand the rebellious nature of young men, properly wearing a suit still means that you’ll do it in a manner that’s appropriate. On top of all, the suit should be well-fitted and colors well coordinated.

One or two modern designs in your closet for fun occasions are fine. But you should fall back on the classics for business and other formal events.

Embrace neutral suit colors. For example, charcoal is a superb color for one of your first suits.

So is a navy suit. Both colors show maturity but can be really versatile, allowing you to play with your formality a bit.

A white dress shirt is practically mandatory if you’re dressing for a professional setting. However, swap out the white for a light blue dress shirt when you can loosen your mood a bit.

In the market for a second suit? Now you can add a fun blue suit for more celebratory events.

Casualwear You Can Embrace in Early Adulthood

You can get away with a lot in your fashion choices at this stage of life, but you don’t ever want your look to be a total mishmash.

Too many eclectic choices in one ensemble look sloppy and careless; it just doesn’t work. Preppy or grunge? Either is fine, but don’t mix elements of both in one look.

Fitted t-shirts, flannel shirts, fitted jeans, khakis, and a decent blazer all make up a terrific foundation for a casual wardrobe.

These basics allow you to switch gears from super laidback to a more smart-casual approach to socializing.

Dark slim-fit jeans with a graphic t-shirt under a hoodie are an iconic outfit for a day of relaxing that you can’t ever go wrong with.

Add a knit cap for some personality and maybe one other accessory, like a casual watch. These show that you make deliberate style choices.

How to Dress for Your Age in Your Thirties

Your thirties bring more responsibility to your life. These require commitment and focus, so it’s time to put away childish things, including your clothes.

Reflecting on your new-found maturity in your dressing choices does some of the hard work for you of showing people how responsible you are.

By now, you have a pretty good grasp of your personal style. This is the time to build on that and expand into some fun, new, grown-up territory.

Formal Attire for Established Men

Your days of youthful fashion experimentation are over, but that doesn’t mean that you can’t begin some new fashion exploration.

Mark your formal flair by incorporating patterns into some of your garments, such as dress shirts and ties.

Raid your closet and dump your old suits that read too young and trendy. But definitely keep the classics if they still fit you well or can be altered to a suitable fit.

Buh-bye to super contemporary cuts, and hello to your charcoal suit. This is also an ideal time to add another professional suit; if navy is missing from your wardrobe, what are you waiting for?

If you only own brown dress shoes, you should invest in a sharp pair of black dress shoes, preferably black whole-cut Oxfords. These will cover your most formal needs.

Proper Third-Decade Casual Attire for Men

Relaxed styles are still acceptable in your thirties, but it’s time to start adopting smart-casual looks into your wardrobe.

Jeans are still perfectly fine, but you should upgrade them to a more polished-looking pair.

You can switch for chinos and pair them with a solid t-shirt and an unstructured blazer or a crewneck sweater for a preppy but laid-back outfit.

To smarten up the outfit for a business casual look, switch your jeans for some light-colored chinos. Round out this outfit with some killer dark-colored Chelsea boots.

A tailored fit is still imperative, even in casual dressing. However, that doesn’t mean you should go directly for super slim-fitting cuts.

Slight tapering at your waist and straight legs are perfect.

Do you want to go beyond the basics? Check out my dedicated guide on how to dress better in your 30s.

How to Dress for Your Age in Your Forties

There are many upsides to approaching middle age, but unfortunately, there are also fewer styles you can get away with now.

Your looks and shape begin to change, so you need to pay attention to how dressing fits your body type.

Once you hit your forties, it’s best to avoid wearing:

• Ripped and faded jeans
• Hoodies
• Graphics on t-shirts
• Logos anywhere
• Sporty sneakers (unless playing sports)
• Super trendy fashions
• Unfitted clothes: either super tight or baggy

Formal Attire for Men at the Height of Career

It’s time for another wardrobe addition! If you have already started playing with patterns in your dress shirts, consider expanding that pattern love to your suits.

A light windowpane or pinstripe pattern conveys confidence and authority. Still rely on a dark background for your suit to keep it more dressy, but the detail of the print adds a nice classy touch.

Wear a white dress shirt with your patterned suit. This keeps your suit conservative and highlights your print. Don’t forget to accessorize! A watch and a pocket square give your ensemble intentionality.

You shouldn’t be afraid to out-dress younger men. Add colors and personality to your outfits and embrace your style with confidence.

As your body changes with age, pay close attention to your suit tailoring. Clear your closet of suits that don’t fit perfectly, or bring them to a tailor if they can be adequately adjusted.

Or, invest in a couple of made-to-measure suits to get that perfect fit and personalized detailing. Above all, choose high-quality fabrics to elevate your look.

Casual Attire Appropriate for Mature Men

At this stage, dressing casually without looking slovenly becomes more challenging. Casual outfits require more effort.

Your wardrobe should include a lot of neutrals. Use bolder shades to accent your outfits.

This intelligent use of color prevents you from appearing like you’re trying to dress younger. Chinos and a patterned dress shirt make a perfect casual outfit when paired with loafers or brogue shoes.

If that doesn’t feel relaxed enough, a polo shirt and dark jeans are another worthy casual outfit.

If you’ve begun to develop that middle-aged spare tire, don’t give in to the temptation to hide it with super baggy clothes. That will only have the opposite effect and emphasize your excess baggage.

How to Dress for Your Age in Your Fifties

By now, you’ve truly settled into yourself. You have the confidence that you need to be able to back up your fashion choices.

You’re totally comfortable with yourself, and you know what styles you like.

If you don’t have a tailor by the time you reach your fifties, what are you waiting for?

This is when you want to pay even closer attention to getting that fit that makes your clothes look as if they were cut just for you.

Formal Attire for Accomplished Men

Your closet is likely full of some beautiful suits by now. You probably don’t need to change the style of what’s already there, but now you should start expanding your styles.

Add some sophistication with a couple of double-breasted suits. Or consider investing in some vests and waistcoats for another dash of elegance.

A nice grey suit accompanied by a dress shirt and a navy tie is a stunning combination of color and culture.

Complete the effect with black derby shoes. This is the best time to embrace a debonair attitude.

Casual Attire for Men in Their Golden Years

Your clothes should be comfortable when you’re in relaxation mode, but comfort doesn’t need to look sloppy.

Lightweight sweaters, like crewnecks and cardigans, are a dignified way to be comfortably laidback. Pair them with dark chinos, which convey a dash of effort.

You can tweak your casual outfits and make them sharper with a bold-colored button-down shirt with an open collar.

You can match them with khakis and toss on a tweed blazer or sport coat when you need to spruce up your look.

Invest in a casual suit or two. You can keep these handy for last-minute social outings.

How to Dress for Your Age in Your Sixties

Congratulations! You’ve gained wisdom. Your sixties aren’t old age; they’re years of experience. You’ve also earned the right to assert your fashion sense confidently.

You don’t need to change much. You’ve already reached perfection, right? (But remember the importance of tailoring! That never changes, no matter which decade you’re celebrating.)

There Are Still Opportunities to Dress Up

If you’re retired, you may find you have fewer reasons to throw on a suit. However, when you do, pull out all the stops. You can’t ever go wrong with a three-piece suit.

But, first, determine if there’s a dress code to dictate how formal you need to go, and let the color of your suit reflect your formality. The darker it is, the dressier your suit is.

Next, include a white dress shirt with a subtle pattern and a colorful tie. Take Jordan Peterson as an example.

Has your hair gone grey? Dark, rich suit tones make a gorgeous complement to your new coloring. Try navy or burgundy.

Casual Attire for Men in Their Senior Years

One of the (many) bright sides of retirement? You have more time to dress how you want to.

Loosen up your casual attire. You can still incorporate dress shirts, but best opt for button-down ones.

Flannel is never a wrong choice. You can still wear t-shirts, but be mindful that they’re a good fit. You still want to avoid baggy clothing.

Cotton pants are a comfortable, conservative choice; consider chinos or cords. If you prefer elastic waist pants, go for it!