Young Men’s Style: 4 Tips To Look Older & Cooler Without Overdoing It (Works For The Older Guys, Too)

I received an email a few weeks ago with a great question.

A young man named Nick wanted to know how to dress well as a teenager when everyone around him at school dresses ultra-casual—think basketball shorts, cargo shorts, T-shirts, and hoodies.

Nick wants to dress sharp with a more grown-up style. Maybe rock some chinos, an OCBD, or a stylish sweater. But he isn’t sure how to pull it off. Plus, he’s worried about his new style standing out too much.

Sound familiar? Probably, because I get this same question from grown men who work in casual office environments, too. They’re sick of looking like they just rolled out of bed and straight into their cubicles. They want to dress up a bit for the office, but without sticking out like a sore thumb.

This is not a problem exclusive to teenagers. The earlier you learn to take control of your style and do so with confidence, the better off you’ll be in the long run.

But I get it. It’s easy for me to tell you, “Just do it!” But putting it into practice? That’s a whole different thing.

In this article, I’m sharing four tips on how to dress well for all you teenage guys out there struggling with your style. That means you, Nick!

Are you a reader in your 20s, 30s, or older? You should still read this article.

These tips apply to men of all ages, especially when you want to dress sharper than the casual crowd around you.

Tip #1: Change Just One Item

Let’s say your current go-to school outfit is basketball shorts and a navy hoodie. You can take that oversized, shapeless hoodie and step it up with a navy sweater instead.

We’re not talking anything too crazy or different. You can even keep the basketball shorts (for now… though you probably won’t want to if your top half is already looking super sharp). Just by changing one item—ditching the hoodie for a fitted sweater, for example—you’re already starting to elevate your look.

What if you tend to wear a plain cotton T-shirt? Change it up by adding a chambray shirt on top. The resulting look is still casual, but adds interest. And it’s a good way to experiment with layering without looking too formal.

The goal is to keep swapping out one item in every outfit. Eventually, you’ll develop a new wardrobe full of upgrade pieces that elevate your style. And since you’re doing it a little at a time, the change won’t be as shocking.

Here are a few more examples of one item swaps you can make to improve your high school style:

Basketball shorts are fine at the gym, or, you know, when you’re actually playing ball… but if you want to grow up your style, stick to a pair of fitted chino shorts when you’re off the court.

Logo and graphic tees not only dress down an outfit, they make you look younger. Nothing wrong with that, but if you’re trying to elevate your look, go for a simple polo like this one.

This isn’t your dad’s farty golf polo. The material feels like a cotton T-shirt. The little details (the fit, the collar) make you look older and more refined, and dare I say, cooler. And if you’re not comfortable with a polo yet, a second runner up would be a plain, well-fitting (not oversized) T-shirt.

I know baggy, oversized stuff is having a moment, but if you want to have a more grown-up style, stick with a more classic look (e.g., pants that actually fit you well, that follow the shape of your leg without being suctioned to it, like a standard straight or slim cut).

Bonus points if you go with a pair of dark wash jeans with no fades, tears, or whiskers. These are the most dressed up you can get with a pair of jeans.

Tip #2: Take Your Time

This is not a race. You want a smooth transition into your new style – not a sudden crash.

A subtle style transition that takes shape over the course of several weeks or months is best. Nothing too jarring or obvious. No sudden changes from shorts and a hoodie to a suit and tie.

Think of your goal as updating your style with as much subtlety as possible. You want people to be impressed by your style, not surprised by it. The perfect reaction is: “That looks great on you!” You want to avoid: “What are you wearing?!”

So move slowly and steadily towards your goal – resist the urge to sprint.

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Tip #3: Embrace Trends

You’re young. You’re in high school. You deserve to enjoy the way you dress. This is the perfect time to embrace trends and try out any new style you think looks cool.

Let’s be honest – one day (much too soon) you’ll feel like you’re too old to pull off the trendiest fashions. So take advantage now while you can.

What’s hot in the music, movies, and celebrity culture you love? Is there a specific artist or star whose look you’d like to try for yourself? Go for it!

If you decide you don’t love it, you can always go back to the classics. But you just might find your favorite new outfits this way. When you’re young, having fun with fashion is all about experimenting with trends and discovering your favorite look. Don’t be afraid to be the trendsetter at your school.

Quick note to the older guys: Yes, you can experiment with trends too. Try thoughtful but out-of-the-box details that update your style and show that you’re paying attention to what’s on trend in the menswear world.

An example of this would be camp collar shirts for casual outfits, and looser (but not baggy / sloppy) pleated, tapered trousers for smart casual looks.

Tip #4: Chill Out, People Really Don’t Care

Reality check: Everyone is caught up in their own world. They’re all obsessed with themselves. It’s true in high school. And it will still be true when you’re older and at the workplace.

So just go all in on the styles you love. Wear what you want and what you like. People don’t really care. But you’ll feel so much more confident and relaxed when you’re wearing something you love.

It’s true, some people will make negative comments. But that nonsense is really a reflection of their own lack of confidence. When you stand out for looking your best, the naysayers are naturally going to worry about their appearance. Their negativity comes from a fear that you’re dressing better than they are… which you probably are.

Or maybe they’re your buddies, but they’re teasing you. Guess what? Your buddies would tease you anyway. If it’s all in good fun, and not mean or malicious, that’s just what guys do. But really, if they’re true friends, they want what’s best for you and for you to be happy. And yes, that includes wearing stuff that you love and feel great in.

You’re Young (Or Young At Heart)! Enjoy It!

Experiment with your style while you’re still a young man. Get to know yourself as a person in the process. You can easily dial it back when you decide you’re not so into that last outfit you tried. No worries.

Eventually, you’ll nail down a solid personal style—one you can continue to craft and improve on as you get older. That way, you’re already ahead of the game with your grown-up style.

Which tip did you find most helpful? Which tip do you want to implement today?