How To Wear a Men’s Sweatshirt

Lester Fangonilo - October 5, 2021


Sweatshirts don’t appear to be the most stylish clothing item you’ll find in anyone’s wardrobe. If you’re feeling the cold, though, it’s a perfect choice - a no-brainer.

We all love a good sweatshirt. It’s useful, laid back, and casual - it can easily take off the pressure of having to decide what and how to wear. However, what you need to understand is that sweats aren’t only functional. When pairing it with the right clothing item, layering it, or wearing it as it is, you can go from casual to stylish in no time with a sweatshirt. 

Here is a comprehensive guide to wearing a men’s sweatshirt with style.

Ways to Wear a Men’s Sweatshirt

Whether you’re dressing up or dressing down, wearing a men’s sweatshirt is fashionable, as long as you know what you’re doing. If you have a jacket, pair of jeans, shorts, and good pair of sneakers, you can rock that sweatshirt without breaking a sweat.

Sweatshirt + Jacket Combo

There are plenty of looks and styles to go with a sweatshirt. From the variety of colors alone, you can mix and match it with a jacket to produce an entirely different look.

  • Bomber jacket

 This is perhaps our favorite way of styling a sweatshirt. Anyone can pull off a bomber jacket, and wearing one with your sweatshirt takes virtually no effort. The sweatshirt-bomber jacket combo is perfect for achieving the smart casual look with a little edge. 

You can pick out a plain bomber jacket in black or navy to keep it minimalist. Wear under it a great-looking sweatshirt, like Oliver Cabell’s Crewneck Sweatshirt in Oatmeal Heather, your favorite jeans, and a pair of sneakers.

  • Leather jacket 

If you want to appear edgy and rugged, nothing works better than leather. Wear a sweatshirt with a leather jacket, and you can transform from an average Joe to a Hollywood action star. The lowly sweatshirt gets a major upgrade with an excellent leather jacket.

You can combine a light-colored sweatshirt with a black leather jacket, or a black sweatshirt, with brown leather. Of course, great-looking black jeans would complete the look.

  • Overcoat

If you want a step up your fashion during the winter months, wearing your sweatshirt with an overcoat will achieve that goal. An overcoat makes any winter clothing item smarter. Aside from being masculine, it’s a classic piece of clothing so you can never go wrong. 

Wear a dark-colored overcoat over a light-colored sweatshirt so that the colors can complement each other. 

Sweatshirt  + Bottoms

If you want a pain-free route to style, simply wear a sweatshirt and pair it with your favorite jeans. You can go from casual to smart casual depending on the kind and color of the sweatshirt you pick and of course, the kind of jeans that go with it.

Want to go full casual? Grab your favorite solid-color jeans and pair them with a plain gray crewneck sweatshirt. That way, you appear smart and approachable. 

What if it’s the summer season and you’re doing a long of lounging? 

Pair your sweatshirt with shorts. You can wear them at home at your Zoom meetings or outside for your daily grocery shopping. 

Another great combination with your sweatshirt for those aiming for a sporty, streetwear, or active look is joggers. Select a dark-colored crewneck sweatshirt to go with gray sweatpants, and you’ll achieve the sports luxe look without trying too hard. 

If you’re gunning for the look of professionalism, wear slacks with your sweatshirt. Complete the look with loafers.

Dressing Up

Sadly, sweatshirts are quite overlooked in the dressing-up business. However, the reality is that men’s sweatshirts are actually versatile items that can grant you leeway to express your style. You can look the part of the smart, no-nonsense professional or the relaxed but preppy everyman. Of course, this stylishness comes with something other pieces cannot - comfort. 

So how do you dress up using a men’s sweatshirt?

Layering: Sweatshirt over a Shirt

If it’s extra cold during the winter months, then layering a sweatshirt over a great T-shirt is a good idea. You can choose between tucking it in to go more street or you could just untuck your shirt. Having your shirt peeking under that sweatshirt makes it edgier.

Of course, if you still want to look smart even with the layering, use a button-up shirt instead of a tee. Have the collar exposed for more flair. Pick a great color palette, preferably similar ones, if you want to look clean and contrasting colors if you want to stand out. 

Layer the bottom with slacks to say you like respect protocol without stressing too much over it. Wear it with loafers and for finishing touches, go for simple but elegant jewelry. Make sure your accessories don’t overwhelm the look since you want the sweatshirt to be highlighted.

Wearing a Sweatshirt in the Summer

Men’s sweatshirts and cold season are not mutually exclusive. You can still manage to look stylish during summer nights wearing a lightweight and comfy sweatshirt. Here are tips on how you can rock a men’s sweatshirt even during summer.

  • Buy only lightweight sweatshirts that are suited for the warm weather. At first glance, two sweatshirts can look alike. However, when you read the fine print, the materials actually tell you which climates they’re more suited to. As a rule, wools and cashmeres are not lightweight and breathable - so scratch those as a possible men’s sweatshirt for the summer. Instead, go for sweatshirts made of cotton, light linen, and rayon.
  • If you want to look preppy, you can wear your sweatshirt around your shoulders or your waist. It makes you look both casual and stylish while being completely practical. You can breathe under the warm summer air when outside and you can also deal with cooler temperatures when indoors during the summer seasons. 
  • When the beach beckons, sweatshirts are a fashionable outfit to those bonfires. It’s not always hot every hour of every day during the summer.  As a matter of fact, in some climates, the night air during the summer is chilly. Therefore, when you’re out partying over a bonfire, don a sweatshirt and pair it with shorts.  
  • Wear a sweatshirt for summer outdoor exercises. Workouts can be intense during the summer - and sweatshirts are a perfect way to up that intensity. Not only will they induce sweat;  they will also absorb sweat that reduces discomfort and overall makes those workouts more enjoyable. They’ll look great on you, too!


So there you go - some tips on how to rock that men’s sweatshirt!

To summarize, a men’s sweatshirt is anything but basic. When used with style, they can be a versatile piece of clothing that works in both cold and warm seasons. So the next thing you need to do is buy one and make it a staple in your wardrobe.

You can buy great-looking and ethically-made men’s sweatshirts from Oliver Cabell.