How to Wear a Sweatshirt in Style This Season

by Jamie Wilson

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

Need to know how to wear your sweatshirts in style this season? Check out our quick and easy style guide and learn how to liven up this classic wardrobe essential.

Sweatshirts have long been associated with sporty types but have evolved into a versatile wardrobe necessity. They’re not just designed for keeping us warm and toasty on cool wintry nights, they’re pretty practical too. Now, where would we be without our quick fix sweatshirts?

Men’s Sweatshirts

Before we take a closer look at how to style this key piece in every man’s autumn/winter wardrobe, let’s refresh our memory on the essential and vital colours in which you should own a sweatshirt. Whether you prefer plain clothing or you want to add interesting designs, these are the absolute must-have tones. No matter how obvious it might be, here are the foundational sweatshirts. Here we go.

Grey Sweatshirt

There’s a preppy element to plain sweatshirts that is often underestimated. Just because they have the same feel of a hoodie, it doesn’t mean that sweatshirts are just for casual or sporty occasions. Wear a shirt underneath your sweatshirt or wear a classic peacoat over it and you’ll be channeling that collegiate charm in no time. Men’s grey sweatshirts look great with joggers and jeans alike, so getting your hands on one of these bad boys is essential.

Black Sweatshirt

The beauty of crew neck sweatshirts in general is that you can usually throw them over anything. This design’s versatility is immediately enhanced thanks to black’s adabtability. That’s the meeting of a style and colour that will go with any piece of clothing you decide to wear. Jeans, trousers, trainers you wear it, the sweatshirt will be the perfect companion.

White Sweatshirt

Just like every man needs a substantial arsenal of white T-shirts, we can say the same thing about white sweatshirts for men. In this case, it’s always good to experiment with interesting branding and logos. With the right graphics on your side, you’ll be stepping up your street style game in no time.

If you’re a fan of the oversized fit, be careful when wearing white. No one wants to look like the Michelin man. However, as long as you keep an eye on the proportions and thickness of your sweatshirt, there’s no way you can mess it up.

Who’s Wearing it Well

Sweatshirts for men are perfect for styling up on those casual days. Kanye West layers up a grey tee with a simple plain men’s grey sweatshirt and finishes his look with a pair of light blue jeans and Chelsea boots. Grey on grey is a pretty strong trend that keeps coming back onto the runways quite often. As long as you integrate different shades of grey, it will always be a successful combination. Just avoid having every tone of grey matched to perfection.

Drake keeps his look simple with a black and white motif on his sweatshirt. You can style it up with a pair of chinos or skinny jeans and your favourite pair of Nike trainers for an effortlessly cool daytime look.

On the Street

We found a good mix on the street of how you style your sweatshirts. You don’t need to stick to plain and simple when it comes to mixing up your look. Why not make a statement? If you opt for a bold printed sweatshirt, don’t stop there. Add a splash of colour with your jacket or accessories and finish your look with a pair of blue jeans and boots.

If you’re going for more of a skater-look, team a simple grey sweatshirt with dark navy jeans and a black trench coat. Don’t forget the shoes, finish off with some white trainers like these ones from Asics.

Denim can add a different take on any style. Go for an edgier more alternative look and add a blue denim jacket over a black sweatshirt for men with skinny jeans and black trainers or plimsolls.

Dressed Up

When you think of sweatshirts you wouldn’t normally link them with being formal appropriate or something you’d wear to dress up but there are a multitude of ways you can smarten up this classic for any type of occasion.


Why not upgrade your sweatshirt for smarter occasions or even the office and ditch the suit and tie by layering up a dark grey sweatshirt, or any colour of your fancy, with a formal button down shirt underneath. You can dress up your look by adding some smart shoes, or dress down with some slip on trainers.


Whether you’re heading to the gym or out with friends, the sweatshirt is a quick fix that you can throw on for any occasion and still be on trend.

Street Style

If you want to look effortless but still bang on trend, pair a crew neck long sleeved sweatshirt with jeans and some classic Chelsea boots. Once you find a sweatshirt you love, it’ll be hard not to find yourself matching it with everything, and anything, you own. Why not dress down in a more casual baggy sweatshirt teamed with your favourite pair of jeans? You’ll still look stylish even when lounging about at home, with barely even lifting a finger!

If you want a slightly more smart casual look, wear with jeans and some smarter shoes. Mix up the colours and pair a sweatshirt with either dark or light coloured jeans and some smart brogues or loafers.


Sweatshirts have evolved a hell of a lot in the fashion world over the last few decades. It all began in Alabama in 1920 with an idea from budding football player Benjamin Russell Jr. He offered a more practical cotton jersey solution to the issues associated with wool jerseys worn by athletes at the time. Wool jerseys were just plain uncomfortable, itchy, prone to shrinking, and made any physical exercise worse with the heat.

They evolved into an aid for athletes, starting off fairly plain with the sole purpose of providing comfort, not style, usually made of thick fleecy cotton. They do exactly what they say they do on the tin, absorb sweat, which is ideal for athletes and sport enthusiasts.

Surfers, skaters, and hip-hop stars began to take to the streets adopting sweatshirts into their own style. With a wave of cool, edgy people wearing them, sweatshirts exploded into a cultural phenomenon. Almost everyone was wearing, or at least owned one, but this time it was for style not just for comfort.

How to Wear A Sweatshirt in Style This Season

  • Men’s sweatshirts are an essential and versatile element that you can work into most outfits. Don’t be fooled by their sporty texture.
  • Make sure that you own at least one in a key colour such as grey, black and white. It might sound obvious, but it’s not something to be dismissed.
  • Formal doesn’t necessarily mean uncomfortable or stiff. Dress up your sweatshirt by wearing a shirt underneath it. Finish everything off with a pair of tailored trousers and formal shoes such as brogues.
  • When it comes to building the perfect effortlessly cool casual outfit, there are so many options to choose from. You can’t go wrong with teaming your sweatshirt with skinny jeans and a pair of statement sneakers.
  • Let’s not forget to thank football player Benjamin Russell Jr. for introducing these cotton jerseys as a replacement for woolen ones.

On That Note

You can still look stylish in a sweatshirt whether you’ve opted for a more casual sporty street look or ramped it up a notch with tailored layers for a more formal look. With the cold nights still making us dream of summer, sweatshirts are perfect for keeping warm and looking on trend every time. If you go for a bold printed sweatshirt, don’t be afraid to make a statement with colour. But if you decide to play it safe and go for neutral tones and keep to the classics, there are plenty of ways to mix up your look and still feel comfortable.

Feature image from Pinterest

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