10 Ways To Get The Skater Boy Look and Pull It Off

Skater Boy 1

The skater-boy look is trendy once again. This iconic style, many remember from the 90s, has gained recent popularity thanks to social media apps like Instagram, TikTok, and Snapchat. The skater boy aesthetic is prevalent among middle, high, and college students, who love the skater style.

This list contains tips and inspiration you need to get that skater-boy style and pull off the look.

10 Ways To Look Like a Skater-boy

Skater boys are taking the fashion world by storm with their unconventional styles and outfits. Here are the ten ways to look like a skater boy:

1. Skate Style Starts With Your Shoes

When it comes to putting together a skater boy outfit, it all begins with the shoes on your feet.

For years, shoe brands like Nike, Adidas, Converse, DC, and Vans have released sneakers designed for skaters. Now, some of the most popular shoes on the market are skate shoes because of the rise of the skate style.

Here are the best:

  • Vans Slip-On
  • Vans Old Skool
  • Vans Sk8-Hi
  • Nike SB Stefan Janoski
  • Nike Blazer Mid 77
  • Nike Dunk Low
  • Nike SB Dunk
  • Adidas Daily 3.0
  • Converse Chuck 70
  • Converse Chuck Taylor All Stars
  • DC Court Graffik

If you're debating on which skate shoes are best for you, it comes down to preference.

Shoe brands like Vans and DC design their sneakers for consumers who skateboard. If you want to fully embrace the authentic skater style, purchasing a pair of DC or Vans shoes is a good choice.

Nike, Converse, and Adidas are all stylish and trendy shoe brands. If you're trying to achieve the skater-boy aesthetic while not skateboarding, these are the shoes you will want to wear.

2. Wear Skater-boy Clothing

The most important part of looking like a skater boy is wearing the proper clothing. Typically, skaters like baggy clothes and are fearless in incorporating different colors, textures, and materials into their fits.


Many skaters will layer their outfits by wearing a baggy sweater or oversized shirt. Throwing on a loose-fitting sweater is an excellent way to add depth to your skater-boy outfit. 

Hoodies, zip-up sweaters, crewnecks, and half-zip sweaters are cool, stylish, and a terrific way to add layers to your attire.


When it comes to tops, skater boys have a few different options. There is the standard t-shirt, graphic t-shirt, long sleeve t-shirt, or v-neck. All these styles have a nice look, and choosing which one to wear, really comes down to personal preference. 

Right now, a boxy-fit shirt is trendy among skaters since it has a baggy look.


Straight-leg jeans, skinny jeans, sweatpants, shorts, joggers, or baggy cargo pants are part of the skater-boy aesthetic. Deciding which pants to wear depends on the look that you are trying to achieve.

Wearing cargo pants or straight-leg blue denim is best if you want loose-fitting pants. A classic pair of skinny jeans or joggers will look great if you prefer a more fitted look.

Choosing the right pants style depends on your body type and the look you like best. Fashion is subjective, so no matter what style you choose, you will look like a skater boy.

3. Get a Skater-boy Haircut

To look like a skater boy, you will need to have the right hairstyle. Getting a skater boy haircut is easy, as skaters have many different hairstyles.

Hairstyles are constantly changing. However, a few haircuts are particularly popular among skater boys right now.

Here are a few different skater-boy hairstyles:

  • Middle Part
  • Messy Undercut
  • Skin Fade Crop
  • Buzz Cut
  • Mullet

Ask your barber for a skater boy haircut. Everyone has a different head shape and hair texture, so choosing the hairstyle that suits you best is a good idea.

If you're unsure what hairstyle to choose, there is nothing wrong with trying a haircut out for a few weeks. Trying out different hairstyles is the best way to find a haircut that suits you right and gives you that skater-boy aesthetic.

4. Wear Popular Skate Brands

A big part of looking like a skater boy is wearing popular skate brands. One of the cool things about today's fashion trends is that many skate brands are a big part of the mainstream style.

Skaters tend to wear streetwear brands, athletic brands, denim brands, and skate brands. If you can incorporate some popular skate brands into your wardrobe, you will be one step closer to looking like a skater boy!

Streetwear Skater Brands:

Streetwear brands like Supreme, Palace, and Dime are trendy among skaters. These brands make a variety of graphic t-shirts, sweaters, skateboard decks, and more. If you're trying to get that skater-boy aesthetic, you will want to incorporate streetwear brands into your outfits.

Sportswear Skater Brands:

Since skateboarding is a physical activity, many skaters wear sportswear brands like Nike, Adidas, and New Balance. Sportswear brands have become so popular among the skating community that Nike and Adidas have shoes and clothing specifically designed for skaters.

Denim Skater Brands:

Since skateboarding was invented, denim has been a big part of skaters' outfits. Right now, Levi's and Dickies are the pants that skater boys across the United States are wearing. The Levis 511 and Dickies men's original 874 have that baggy style that skaters love.

Skate Brands:

To look like a legit skater, you will want to wear skate brands. Skate brands like Polar, Obey, Noah, Thrasher, and Vans are very popular among skateboarders and staples in the skate-style world. Wearing skate brands is a great way to take your outfit to the next level and fully embrace skate culture.

5. Layer Your Outfits

A popular trend among skater boys is to layer your outfits. Whether you wear sweatshirts, jackets, or a hoodie, a layered outfit is a great way to incorporate your own personal style into your outfit.

A look you'll often see on skateboarders is a polo t-shirt topped with an oversized hoodie. This look has that baggy style that so many skaters love. Mix this with a pair of Levi's jeans and some Nike Air Force 1s, and you've got a layered skater-boy outfit.

If you're not a fan of baggy clothing, you can't go wrong with a graphic tee layered with a bomber jacket. Wear some skinny jeans and a pair of Vans Classic sneakers to top this outfit off. This outfit has a more fitted look, the perfect mix between functionality and style.

6. Accessorize Your Outfit

A skater-boy outfit is only complete with accessories. Skater boys use accessories to level up and add character to their outfits. Here are the different ways that you can accessorize your skater-boy aesthetic:


Adding jewelry to your outfit is a good idea, whether it's a watch, rings, bracelets, necklaces, chains, or piercings. Silver or chrome chains and rings are popular among skater boys.

The cool thing about jewelry is that there are so many different options. Feel free to try something totally different and purchase an unconventional piece of jewelry.


Among skater boys and in mainstream fashion, many guys have started to wear different styles of bags. Of course, there is the classic backpack. However, you'll see skaters with crossbody bags, satchels, and fanny packs.

Brands like Palace, Vans, and Supreme each sell their styles of crossbody bags designed for skaters.


A snapback, beanie, baseball cap, bucket hat, or trucker cap are all excellent styles of hats skater boys often wear. If you need more time to style your hair or want to try something different, feel free to put on a hat.

Hats are a big part of skate style and street fashion. As a guy, putting on a hat is the most efficient thing you can do when leaving your house in a rush. A few hats for middle school, high school, or college are a good addition to your wardrobe.


It may not seem obvious, but there are a few ways to accessorize your footwear. The first thing you can do is change the laces. By putting on different colored laces, you'll have your unique style, and your shoes will look like no other.

Another way to accessorize your shoes is by wearing fun socks. Socks with a unique design will draw attention to your shoes and add layers to your outfit. Skater boys like to wear socks with designs because it's a great way to express themselves through their clothing.

Alternative Accessories:

Alternative accessories like keychains, lanyards, sunglasses, and a belt are some accessories that you should consider adding to your skater-boy outfit. These accessories are a great way to express yourself and accentuate your personal style.

Many streetwear, sportswear, and skateboard brands sell keychains and lanyards. If you want to represent your favorite brand, consider buying one of those accessories.

7. Embrace Skate Culture

Embracing skate culture is a big part of getting the skater-boy look. By understanding the culture, you will be ahead of the curve on the latest trends among skaters and understand skater lingo.

An essential part of skate culture is understanding its roots and history. Skate culture began in California during the 1960s when surfers wanted to practice their tricks on land. Over the years, skate style built itself on being different, focusing on individual expression and being rebellious.

Another part of embracing skate culture is immersing yourself in the music that skaters enjoy. Even though “Sk8er Boi” by Avril Lavigne is the most famous song about skaters, this song does not represent the skateboarding community.

Skaters will listen to several genres of music, such as Rock, Punk, Pop-punk, Grunge, and Hip-hop. By immersing yourself in the music that skaters enjoy, you will better understand skate culture.

8. Learn To Skate

You can skip this step if you only want to assemble a skater-boy outfit. However, if you plan on thoroughly embracing the skater-boy look and skate style, then learning how to skate is a good idea.

The good thing about skateboarding is that there's a low barrier to entry. Learning how to get on a skateboard and ride around can be achieved after a few hours of practice.

Where skateboarding gets tricky is when you're trying to learn tricks. If this is the case, the best thing you can do is check out your local skate park and learn from others.

Other skaters are usually kind to new skaters and are more than willing to help. A skate park is also a great place to meet others in the skate community and better understand skate culture.

9. Pay Attention to The Details

There are a few minor details that many skaters do to level up their outfits. Pay attention to the little details and incorporate them into your style to really look like a skater boy.

One thing that almost every skater is doing right now is cuffing their pants. By cuffing your pants, you can also show off your socks and kicks.

When skaters are putting together an outfit, they don't strive for perfection. Not striving for perfection means it's okay to wear ripped clothing or clothes that don't look clean. As a skater boy, wearing some clothes that look worn in will add depth to your outfits.

Skater boys will do little things, like wearing different colored shoe laces and tying their hoodie laces together. These small details are a great way to add your own personal style to your skater-boy outfit.

10. Don't Try Too Hard

There is nothing more unlikeable among the skating community than someone trying too hard. If you go to a skate park and pretend to be someone you're not, skaters will call you out and label you a “poser skater.”

There's nothing wrong with embracing skate culture and enjoying the skater-boy aesthetic. However, don't pretend you're an actual skater when you are not!

Final Thoughts on How To Get The Skater Boy Look

Skate style is a popular fashion trend, so there is no reason you shouldn't incorporate the look into your outfits. Wearing skate-style shoes, baggy pants, or a skater-boy haircut are excellent ways to level up your wardrobe and add layers to your personal style.

This article was produced by Wealth of Geeks.

Author: Ethan Schattauer


Ethan is the founder of whattowearmen.com, a lifestyle website that provides practical fashion and style tips for men of all ages. Ethan’s mission is to to help men look and feel their best, with relatable and helpful advice.