Skip to main content

The Manual may earn a commission when you buy through links on our site.

Men’s fashion tips: How to style a sweatshirt for every occasion

Wear the ultimate casual shirt for every occasion

Man in rose sweatshirt, rose boots, and light denim
KC Stone / The Manual

The sweatshirt is one of the quintessential garments in a man’s wardrobe. Let’s be honest: we all love the opportunity to get home from work or a long day, ditch the professional suit or the business casual wardrobe, and opt for the cozy crewneck sweatshirt. Of course, it is easy to wear one of these garments while lounging around the house and binging the Fast & Furious franchise. But just like the underrated hoodie, they are suitable for so much more than simply lounging. This article will show you how to wear one of these men’s fashion classics in virtually every situation.

And don’t worry, we won’t leave you hanging on where you can find the garments in the images and how you can steal the looks. For instance, here is where you can steal the above look if you are so inclined.

Sweatshirt – Athletegy Supima Team Sweatshirt in Rose is the modern upgrade to the sweatshirt. Not only is the color contemporary and all the rage but it is made by athletes, so the comfort is without equal.

Jeans – Devil Dog Boot Cut in Ash is a great pair of jeans that will be your go-to no matter what the day has in store for you. Made by the best with the best in mind, you can never go wrong with Devil Dog.

Boots – Red Wing Dusty Rose Heritage Boots are their foray into fun holiday fare with a released rose-colored boot perfect for Valentine’s Day. However, this boot looks great on any Wednesday, not just the one made for date night.

Man in green sweatshirt and black joggers
KC Stone / The Manual


This may be the most common way to wear a sweatshirt when you go out. It seems like it is easy to simply throw a sweatshirt on and leave the house. If you are gearing up for the big game and realize you don’t have everything you need for the dip, there is no reason to get glammed up. Just throw a sweatshirt on and take off. But there are other things you can do to keep it casual while also making it look like you are dressed on purpose. For instance, swapping the boring sweatshirt for something with a little more personality, like this American Giant piece, gives your look more depth. Swapping the boring denim out for a good pair of joggers is a way to add a little life to your last-minute trip to the supermarket. Also, if you just happen to run into someone you have a crush on, you look like you are more put together and less like you just mowed the lawn.

Steal the look

Sweatshirt – Dave Ortiz Inside Out Collection is sold out, but here is a great replacement: American Vintage Unisex Crew in Brass gives you the same uniqueness and pop of color.

Joggers – DUER No Sweat Jogger in Black will be some of the most comfortable pants you wear, and they will look as great as they feel. This is the definition of comfortable style.

Shoes – Suaves The Zilker in Heather Gray are perfect for your last-minute outing to the store. Forget putting on socks; these feel just as great without them.

Watch – Praesidus Rec Spec is a throwback to a 1960s Seiko that found its use on the wrists of Vietnam soldiers. Now, it is the perfect conversation starter to upgrade your casual outfit.

Glasses – Tomahawk Shades Neuralyzers in Matte Black give you the perfect cap to any outfit, especially the ones calling for black accessories.

Man in rose sweatshirt, joggers, and burgandy shoes
KC Stone / The Manual


Athleisure is all the rage now. While we used to wear suits to work every day and never leave the house without being dressed for any occasion (never forget your fedora), we have now adopted the practice of using clothing initially designed for athletic activities for everyday wear. Athleisure companies leaned in hard and now provide garments for you to wear almost anywhere. Sweatshirts lend themselves quite well to athleisure, and this Athletegy sweatshirt paired with some athletic joggers and sneakers will always be a great look. Keep in mind that athleisure gear should be kept separate from your actual gym gear. Athleisure is also the best fit if you want to wear hoodies out on the town as well.

Steal the look

Sweatshirt – Using this Athletegy sweatshirt accomplishes two things. One, it shows how well this rose-colored shirt looks with navy pants. And two, it displays how versatile a sweatshirt can be.

Pants – Avi Pro Jogger in Saphire Blue is the perfect athleisure pant. It may be made specifically for pickleball, but these pants are about to be a rage as big as the game itself.

Sneakers – Kizik Milan in Merlot is a great addition to this look. Not only does the merlot color play well off the navy and the rose, but it also separates the look from a gym outfit to a great streetwear look.

Watch – Citizen Promaster Dive Automatic brings the blue together with the classically striking blue dial. And, of course, every outfit is better with the right watch.

Glasses – Tomahawk Shades The Recruiter will be the most versatile sunglasses in your collection. Because they are clear, they could go with virtually ANY of these outfits…but here, they looked the best.

Man in white sweatshirt, jeans, and boots
KC Stone / The Manual


Let’s talk about wearing a sweatshirt but still wanting to be the talk of the event. If you want to wear your sweatshirt in a more elevated style, the key is to let the rest of the outfit do the talking. Go a little more basic or clean with the sweatshirt, like this cream-colored piece from Express. Then, you can choose to go a little more basic with the denim or go all out with some patterned dress pants. The key is to find some pieces to stand out and add color. For instance, a unique and elevated shoe or a watch with a pop of color like this outfit will keep you looking fantastic without having to go all out. Comfortable luxury combined with stylish subtly is the pinnacle of being a great sartorialist.

Steal the look

Sweatshirt – The Express piece is long gone, as this has been a staple in the wardrobe for two years now, but the Banana Republic French Terry Sweatshirt can pick up the slack.

Jeans – Mugsy Toasties Flannel Lined Jeans are the perfect companion for your cold days, and since they feel like sweatpants masquerading as jeans, they will keep you dangerously comfortable at the party. Seriously, I wouldn’t wear them when you are driving; you may fall asleep.

Shoes – TAFT Dylan Boot in Salt is precisely what the doctor ordered when you are looking for a piece to make a statement alongside your sweatshirt. They are stunningly gorgeous, and if your jeans are putting you to sleep, people will be waking you up to compliment them.

Watch – Citizen Promaster A -T, with its striking green dial, is the pop of color that your outfit needs, and virtually every other outfit needs it as well.

Glasses – Prive Revaux The Maestro in Havana is yet another eye-catcher. The tortoiseshell color works with almost any earth-toned outfit and fits in nicely with this basic outfit with trendy edges.

Man in black jeans, sportcoat, and sweatshirt
KC Stone / The Manual

Date night

Making a great first impression is hard enough without having to worry about being uncomfortable. Of course, a sweatshirt may not be what you first think of when you think of a great look for a first date, but it can be. And we can prove it. If you do it right, a casual sports coat over most things will elevate your look to date night quality. This black and gray ensemble looks just as good for late afternoon coffee or drinks as it does for the after-six dinner date. Pro tip: A sweatshirt with a tweed jacket can be quite toasty, but don’t do this if it gets hotter than 80 degrees.

Steal the look

Sweatshirt – L.L. Bean Comfort Camp Crewneck Sweatshirt is the basic you’re looking for. And the gray color keeps it a blank slate, so you can dress it up or dress it down.

Jacket – If you want a look that is the same as above, you can shop around or save time and opt for a bespoke option instead. Alton Lane is one of the best out there and can get you a great tweed look with the elbow patches. Or anything else you want to try.

Jeans – DUER Performance Denim in Black Relaxed Taper reminds you that just because you may be nervous about meeting someone for a date doesn’t mean you can’t be comfortable. Paired with a sweatshirt, you will be calm and relaxed all night.

Boots – Amberjack The Boot in Obsidian is the classic low-profile look you need for comfort, class, and memorability. You may be wearing a sport coat, but that doesn’t mean you have to wear dress shoes; keep it casual but elevated with a cap toe.

Watch – Citizen Promaster Skyhawk A – T, with its blacked-out look, is one of the sharpest watches you will find. Any outfit needs a great watch, and Citizen is one of the best at great watches.

The sweatshirt is a casual garment but one that can be versatile if you know what you are doing. Hopefully, you have the knowledge you need to go out and rock the casual in elevated ways.

Editors' Recommendations

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
The hottest men’s denim trends: How to update your casual wardrobe
Check out these looks if you want stylish jeans for men
jeans stacked on store shelf

No matter the season or the current trends, denim will always be an essential part of your wardrobe. Whether it’s in your jeans or jackets, denim is essential for any closet, and 2024 will be even more significant for this classic piece. While everyone has their opinion on the baggy versus skinny denim debate, the truth is that this year will see trends explore wider and more classic denim pieces. Focusing on denim jeans, these pieces will get baggier and wider but still have a timeless sense that makes them worth the splurge. Investing in the right denim pieces means having quality items in your wardrobe for years. 

With many fashion trends seeing a bolder look recently, these denim trends aren’t holding back. Many of these trends are based on the return of older fashion eras with a bit of a modern twist to them. While some denim trends might need more courage to pull off, some are perfect for a more traditional look. With head-to-toe denim looks a current fashion must-have in your wardrobe, it’s time to start looking at what 2024 holds for all of your denim pieces. 

Read more
The 3 types of suit lapels (and how to know which is right for you)
Let professional tailor Jeffrey Appelson teach you about lapels.
Gray sport coat on rack

A man's suit is one of the most elegant pieces in his wardrobe. It is what you wear to land new business. You slide one on when you are attending a momentous occasion like a wedding. You choose your black or charcoal suit when you have an after-6 pm event. And you choose the same when you mourn loved ones at a funeral. Suits are our best friend, our constant companion as we go through life. Of course, that means you have to get to know your favorite tailored garment. There are a dozen things to understand and learn when you are just starting out, and one of the most important parts of the suit to learn is the lapel.

The lapel is the front and center of the suit. While the shirt and tie create the arrow pointing to your face, the lapels form the framework that can either make you look formidable and confident or sheepish and disappear into the crowd. Of course, we could tell you all about our experience with suit lapels, but as always, we would prefer to speak to someone in the industry and let you hear it from those who make them. We sat down with 13-year industry veteran Jeffrey Appelson, owner of Jeffrey Scott Bespoke Suits out of Princeton, New Jersey, to get his take on the feature.

Read more
The 5 tweed pieces every man needs in his closet
How to wear tweed, jackets, blazers, and more
man wearing tweed jacket

If you want to add sophistication and elegance to your closet, one of the easiest ways is by adding high-quality materials and fabrics. One of these materials, tweed, is known for its elegant texture that can add a significant touch to your wardrobe. While many will know classic pieces like tweed coats or blazers, there are plenty more pieces that you can add this material to. 

Everyday tweed pieces are easy-to-add pieces that can help make your casual items seem much more expensive than it is. Being sturdy and thick, tweed also gives you the benefit of being a long-lasting material that, with proper care, will last for many seasons. If you’re looking to splurge on timeless items that add to your style, you can’t miss a good tweed piece. 

Read more