How To Dress For Your Age (20s, 30s, 40s, 50s+)

September 17, 2021 By Jamil 0

Shakespeare talked about “the seven ages of man.” Happily, we guys only need to dress for one of these ages at a time!

There’s a certain dignity to dressing your age… and there are consequences to violating this rule.

A 45-year-old overweight man with graying hair wearing board shorts and a graphic tee oftentimes looks like a joke. But so does the college student attending lectures in a $3000 bespoke 3 piece suit.

In both cases, neither man is dressing his age. Although it’s possible to make these outfits work they just look better when key factors like environment, career, message, and age are taken into account.

Casual dress for the young man

Young men can usually wear just about any style as long as they’re willing to really own it. That means no half-measures — funky, bright-colored trousers mean a mix-and-match look in the rest of the outfit; don’t pair them with plain black dress shoes and a pressed white dress shirt. You’ll confuse people.

#1 Pick one theme

When you put an outfit together, you want to aim for a look that can be described in one word. (This is good advice for all ages, but especially helpful for young men, whose experimental wardrobes tend to be more varied). Do you look at outfits with a ‘preppy’ or ‘grunge’ theme? How about a ‘hipster’ look? If you’re looking like a little from each all at once, you probably need to change some items around.

#2 Vary your look

Style for 20 year old guys should be about experimenting, figuring out the kind of image you want for yourself. If you’re a college student who wears khakis and a polo shirt every day, I highly encourage you to go outside your comfort zone. Play around a little. I’ve never met a stylish young man who didn’t have a wide variety of tops and trousers (to say nothing of accessories) in their closet.

Varying the look from day to day keeps yourself from being pigeonholed. Dress sharp one day in a tucked-in dress shirt, slacks, and a dark blazer, then switch to bright corduroys and a henley under a denim jacket the next. And so on.

#3 Accessorize

What’s the difference between a guy in jeans and a hoodie versus a guy in jeans and a hoodie with a leather bracelet?

Quite a bit, actually.

Having an eye-catching accessory somewhere in an outfit makes it clear to people that you have self-control and you’re wearing a deliberate ‘look’ rather than some mismatched pieces grabbed at random out of your closet.

This is especially important for casual outfits, which can look like classic youthful sloppiness if you’re not careful. Sharp-looking accessories mean that even if the older generation doesn’t like your style, they must concede that it is a style.