5 Easy Tips for Dressing Like an Adult (2023 Men’s Guide)

The other day I spotted a young couple in the subway. They appeared to be somewhere in their late 20s to early 30s.

It was a beautiful Saturday afternoon, so I assumed they were spending the day together.

The young woman was smartly dressed in a wool turtleneck sweater, loose fitting knit trousers, modest heels and a nice handbag. A classy New York outfit perfect for brunch or lunch in a nice Manhattan bistro.

The young man, on the other hand, was wearing ill-fitting faded jeans, a red sweatshirt/long sleeve t-shirt with some type of graphic on it, running shoes, which have seen better days, and a multi-colored nylon backpack.

“What’s wrong with how he was dressed?” you might say.

There’s nothing wrong per se with his outfit, but in comparison to his partner, he was dressed like your average 13 year old boy.

I believe the only time you could get way with dressing like a 13 year old is if that 13 year old is your son and it’s something like ”Father and Son Dress Alike Day.”

If not, then it’s definitely time to upgrade your wardrobe. If this sounds like you and you feel you’re ready to start dressing like a mature man, then keep reading.

Here are 5 simple things you can do to elevate your look from frat boy to a stylish adult.

Upgrade Your Jeans and Shorts

For a long time I wore jeans practically every single day. Truth be told, they were the only pair I had. Sound familiar? Lots of guys wear nothing but jeans, sweatpants and in the summer, shorts.

Now there’s nothing wrong with jeans or shorts, as long as those jeans are not worn out, full of holes and bunched up at the ankles.

A nice pair of tailored, dark wash jeans will go a long way.

Want to bring it up a notch? Try a nice pair of chinos. In the winter, throw on a pair of wool trousers and in the summer, a pair of linen pants are perfect.

These upgrades are very simple and easily elevate your look from frat boy to mature man.

Oh, and please leave the sweatpants for the gym. 😉

Upgrade Your Footwear

Men love to wear sneakers. Heck, some of us wear them way after they should have been tossed out.

Now I’m not saying you need to completely stop wearing sneakers, but unless you’re trying to look like Steve Jobs, leave the running shoes for the track and switch them out for a pair of simple minimalist sneakers.

Something like Greats’ Royale, Koio’s Capris, or any other type of minimalist style sneakers, preferably in white or black.

Want to bring it up a notch? Switch to a pair of comfortable Chukka boots or loafers.

Both work well with a pair of jeans, while giving you a more stylish look.

Upgrade Your Shirt

I get it, you’re a Marvel or Star Wars fan and you want everyone to know. Hey, I’m a fan, too, but let’s leave the graphic t-shirts for when you’re attending Comicon.

It’s time to move away from those graphic t-shirts and move on to something more mature. Think collar and buttons. An Oxford Cloth Button Down (OCBD) shirt is perfect.

The OCBD goes great with everything from jeans to chinos. It looks great with the sleeves rolled up for a lazy Sunday brunch look or with a tie and blazer for a bit more sophisticated look.

If that’s moving too fast for you, try a polo shirt or even a henley.

Think of these two as the more stylish version of the t-shirt. You get the same feel as a t-shirt, but the addition of a collar and/or some buttons and you now have a more stylish look.

Upgrade Your Headgear

One piece of clothing that I feel definitely gives a man a more juvenile appearance is a baseball cap, even more so when worn backwards.

To elevate your look, replace the baseball cap for a stylish flat cap. Is there anyone more stylish or bad ass than Thomas Shelby from “Peaky Blinders?”

Want to turn it up a notch further? Try a fedora. The right fedora can give you that sophisticated Don Draper from “Mad Men” look or, if you’re really daring, that rock and roll look of Johnny Depp.

If you’re just not quite ready to get rid of the baseball cap altogether, stick with a simple solid color baseball cap with either no graphics or very minimalist graphics.

And for Goodness sakes, whatever you do, do not wear it sideways or backwards. This screams frat boy or 80s rapper.

Upgrade Your Backpack

Personally, I haven’t used a backpack since my college days.

My bag of choice, until about a year ago, was a leather messenger bag. A messenger bag, whether leather or canvas, gives you more of an adult look.

It’s also easier to wear on those days when you’re wearing a blazer. A nice leather bag, preferably with a removable shoulder strap, works well in and out of the office, too.

Now if you prefer a backpack, look for something with a clean, minimalist design. Avoid nylon backpacks with multiple zippers and go for something cleaner, like Aer’s Day Pack or Carl Friedrik’s Bowen Backpack.

Both are simple, yet very stylish choices.

Aer is better for minimal, streetwear type aesthetics, while Carl Friedrick is great for rugged, preppy and refined looks.

Closing Thoughts

So basically, that’s all it takes to upgrade your look. Now you may say, “I like the way I dress” or “My wife/girlfriend has no problem with the way I dress.”

Well, that’s fine. My intention is not to make you feel bad about how you dress or mock you in any way, but I can tell you that once you do decide to upgrade your look, things will change.

So go ahead and implement these 5 simple changes into your wardrobe today and see how simple it is to go from frat boy to stylish adult.

Welcome to adulthood.