Dressing the (Younger)Man

A lot of my readers are younger men and today I want to specifically help you out. As I’m sure you’ve noticed around you, the majority of high-school and college-aged guys dress pretty poorly. The benefit to you is that it doesn’t mean you have to bring your A game everyday or invest a massive amount into a new wardrobe to be able to outdress your peers. It’s not too tough when most of them look like this.

college guys in sweat pants

As I addressed in my post on helping older men dress well, age plays a huge factor in what a man can and cannot wear. There are certain things (like a fedora) that really only look good on men when they’ve reached a certain age and others (like neon colors) that have an early expiration date. Younger men have a lot more leeway when it comes to eccentricity and peacocking but should still stick with the fundamentals of classic style. Here are some good guidelines:

  • Fit is still king. You can wear a graphic T-shirt and holey jeans as long as they fit right.
  • An older man’s High/Low should be as dressy as you get. Obviously there will be exceptions that call for more formal clothing (formal weddings, funerals, church, job interviews) but you don’t want to be the overdressed guy. If you’re younger than a junior in college dressing up too much comes across as either geeky or overly affected. When your peers are wearing sweats and T’s you can get away with slim jeans and a button up instead of wearing a suit to class.
  • Embrace trends cautiously (but still embrace them). This advice applies to all men but younger guys have more freedom for jumping on trends. Jewelry, loud colors, short jackets, and others are all much more acceptable if done in small doses. Only have on one or maybe two trendy items at a time. You should be able to show that you’re current instead of looking like a try-hard fashion model.
  • Shoes are key. Stick with low profile sneakers or desert boots. You don’t need to be rocking a pair of Aldens to contrast everyone else’s Seinfeld sneakers and flip flops. 
  • Untuck your button-up shirts. But, make sure they’re casual button-ups and are supposed to be worn untucked. Tucking in your shirt is for older guys and more formal situations.
  • Know that style is more than just your clothes. Pay attention to things like backpacks, gym bags, and school supplies. None of them will make or break your style but they’re all things that can be used to top off your look.
  • Ditch the hoody. Instead you should be wearing  a sweater (cardigan, V-neck, crew neck) or a blazer. You can go with a navy sportcoat year round or wear something seasonal like tweed in the cooler months and linen in the spring and summer.
  • Don’t make a big deal out of your clothing. It should be a natural expression of who you are. If you geek out on a date about how stoked you are to get your new APC jeans no one will want to hang out with you. That’s what the Internet is for.
  • Wear school gear in classic ways. Buying a scarf or a vintage-logo baseball hat to wear to the games is going to look a lot better than all the overly-branded stuff schools are selling now.
  • Get in shape. You will never have cheaper, easier access to gym equipment than you do in college.
  • Wear V-neck T’s or henleys instead of crewnecks. Showing a bit more of your neck and chest will help you look more masculine and confident. Just don’t get into man cleavage territory.
  • Trade out the baseball hat for a driving cap. You can still throw it on when you slept it but it looks much more intentional.

young casual stylish man

These rules are all pretty simple, but stick to them and you’ll be able to look your age, but like you’re ready to start taking over the world as well.

PS. Did you know I do private style consultations? I can help you dress better according to your budget and your needs.

Topman US

Meet The Author


Tanner is the founder and primary author of Masculine Style. He lives in Salt Lake City, Utah with his wife and two kids, and helps run Beckett & Robb – a men’s clothing company built around custom suits and shirts.

  • Thank god, I’m already doing most of what you said. I should probably switch out my pair of skinny jeans though. Ha.

  • Also, sneaker wise do Vans get your tick of approval for young guys?

    • So long as you either skate or ride a bike, or you wear the old-school versions.

  • Peter Phoenix

    Respect for putting in a post for the younger guys (I’m 21). I’ve been working on my wardrobe for a while now and it’s been making slow improvements thanks to you!

  • Robert Espe

    So, how young is “young”? You’ve addressed young, and old, but there is quite a bit in between, and where exactly are the lines?

    • There’s a more discinct line between young and old than old and older. I’d say once you’re done with college, working a career, more than 25, made journeyman, etc. is when you need to start dressing for the respect you’ll demand as a man and not to just look stylish.

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