How to Dress Like a Skater

If you frequented skate parks in the 1990s or 2000s, you probably don’t need this article telling you how to dress like a skater. Back in the early 2000s, I was one of those kids at the skate park every week. I was horrible at skating but would try my hand and hang out with my other skater friends in our flannel shirts, Vans shoes, and backpacks. We thought we were the raddest kids around, and to be honest, you’ll still catch me in flannels and a pair of Vans — once a skater kid, always a skater kid.

Whether you’re looking to mix up your personal style or throw together a quick Halloween costume, read on to find out how to dress like a skater.

Dress Like a Skater 101

Skate Shoes

Forget the new flock of electric skateboards. Today we’re focusing on the more classic skater style and the simplicity of a deck, trucks, and four wheels. We’re starting from the bottom.

Are you a Vans or a DC kid? Vans were the hallmark of 1990s and early 2000s skate culture, and the grip, comfort, and style made them an excellent choice for wearing all day, to school, to the mall, or the park. Your favorite pair of skate shoes back then was probably caked in shoe goo because of how we tore through them, but a pair of flat, rubbery soles are the perfect start to skater style.

Baggy Pants

Next up is pants. In the summers, it is all about denim men’s shorts when it comes to style. If it is a little chilly out, donning a pair of chinos or baggy pants are the way to go. You can even add a wallet chain for a little extra flair.

No matter which pants you choose, make sure you can move in them. Skaters need to be able to throw back an ollie or a kickflip and have the freedom to move. Skater pants aren’t tight fitting.

skater on the beach

Big Ol’ Shirts

Up top, donning a tee from your favorite skate shop or company is, of course, the best option, and on top of that, you’ll want a hoodie or a flannel shirt.

I’m more of a flannel person myself. As a young skater, I used to go to Goodwill and look for the largest, coziest flannel I could find and rock that at the skate park. You don’t’ have to go with thrift, but a dark-colored button-down shirt is essential to a skater look.

If you aren’t excited about the idea of flannel, a hoodie will do just fine and will probably keep you a hair warmer. Make sure whatever you choose moves with you.

Packs and Shades

Lastly, a classic American-made backpack and sunglasses round out your skater attire; you might even throw in a beanie for good measure. These accessories will complete your look, whether you’re off to skate or just want to get sink into some nostalgia.

Skate on, friends, and have a radical day!