A great graphic sweatshirt needn’t be fussy, but it should definitely be perfect. It should have a killer design, something that pops on its own but also plays nice with bold sneakers and a suave hat.

It should be slim enough to easily slide under a tweed blazer or lightweight parka, but never tight or constricting. It should be butter-soft, but also structured enough to maintain its shape after a few years of wear. Most importantly, it should give off the vibe that you are both very cozy and super polished—a man who takes his leisure seriously.

A lot people tend to think of a sweatshirt as a heavier version of a T-shirt, and while that POV is totally valid, we’ve found that when you consider them the same way you do sweaters (sporty, but still a little dressy), your styling options go through the roof.

As always, it’s all about using more expressive pieces to anchor your look and then surrounding them with easy to wear basics like chinos and blue jeans to make your own statement. Join us as we explore some under the radar sweatshirt styles that are casually cool in all the right ways.


BLOCK IT
Pay homage to the golden era of sportswear by rocking an ‘80s-inspired color blocked Champion hoodie. For a nice upmarket touch, look for one with fancy embroidery on the front. When styled with some fitted dark denim and a pair of on-trend retro Nike Cortez running shoes, this is an untouchable look.


ARTS + LEISURE
Flex your taste in music and style by rocking a hoodie from your favorite band or label. Or better yet, kick things up a few notches by investing in a limited edition collaboration, like this epic white hoodie from NYC beatmasters Fool’s Gold and legendary downtown photographer Ricky “Homeboy, Throw in the Towel” Powell. It features an ill portrait (shot by Powell, natch) of god MC Kool Keith hanging out at dearly missed hip-hop superstore Fat Beats back in ‘99. That’s wearable culture, y’all.


DIY OR DIE
From Gucci to Etsy, handmade and DIY clothing is huge right now. Rock this trend the right way by purchasing a unique custom embroidered sweatshirt from an actual mom-and-pop business, like this handsome applique version from Brooklyn-born underground clothing kings Leisure Life. In addition to supporting a sustainable fashion line (all of the letters for the sweats are made from recycled fabrics), you also get a beautiful, one-of-a-kind piece handmade with love by a real person—the definition of affordable luxury.


SWAG U
You don’t need to be fancy to dress smart. Take a page from rakish rebels like Jean-Michel Basquiat and rock a heather grey collegiate style sweatshirt with some relaxed fit jeans and a loose fitting overcoat. And while modern brands like APC and Asos offer cool modern iterations of this classic piece, we would advise you to dig around on eBay for an authentically vintage version. Word from the wise: Don’t settle for your safety school this time!


TWO TONE
While we wouldn’t steer you towards a lot of the other 90s inspired trends (Seinfeld sneakers, anyone?), rocking a contrast collar sweatshirt will make you the Zack Morris of dressing jiggy. To really nail the look, style your two-tone sweatshirt with some white chinos, wild style socks and a pair of sporty penny loafers. Too dressy for you? Simply pair with light denim and a white sneakers for a foolproof minimalist kit.