Had COVID hadn’t turned 2020 into the craziest year I’m not sure I would have thought to do a post on sweatshirts. Sweatshirts have always been afterthoughts tucked away in a drawer that I would only break out and wear on cold trips to the gym. Now that we’re living in a world where we’re playing 2020 Apocalypse Bingo (who had murder hornets?), we’re all doing and wearing things we wouldn’t have worn or done otherwise.

I recently bought my first sweatshirt. Sweatshirts are like umbrellas for me. I rarely buy them, I accumulate them. It made me notice how fashion has responded to this strange year by offering a wide range of clothing meant for a more casual lifestyle. I am going to show you how to style a sweatshirt by sharing five different looks. If you’re looking for where to buy some stylish sweatshirts, also be sure to check out the additional styles at the end of this post.


Outfit #1


This Zella wrap sweatshirt, also available in plus size, is both chic and functional. It’s perfect cool early fall days outdoors and for brisk walks to the gym. I styled it with a long sleeve striped t-shirt from Halogen, black ponte pants from Spanx, a pair of black wedge sneakers, and a burgundy bag from Cuyana.

Outfit #2


This sweatshirt from FRAME is so un-sweatshirt-y looking and easy to style in an elegant manner. I styled it with a pair of burgundy wide leg cropped pants from Vero Moda, a pair of flat python waterproof loafers from Blondo, a grey crossbody from ALLSAINTS, and colorful huggie hoops from Kendra Scott.

Outfit #3


This sweatshirt from Boden with a pair of satiny joggers from Ted Baker and finished the look with flats from Birdies. This look is elegant yet rife with comfort.

Outfit #4

casual tops

This easy sweatshirt from Old Navy has a cute split back that adds some novelty to a basic casual look. I styled the sweatshirt with olive slim leg cropped pants, flats in taupe, and an olive tote, all from Everlane.

Outfit #5

casual tops

What I like about this sweatshirt from Rag & Bone is it looks more like a v-neck sweater than a sweatshirt making it easier to achieve comfort and style at the same time. Additionally, with people looking to machine wash more and dry clean less, a sweatshirt like this is much more wearable than a sweater.

I styled the sweatshirts with a pair of cropped mini bootcut jeans, leopard calf-hair flats, silver hoop earrings, and a black leather hobo bag.

Shop for Sweatshirts

Ready to add some sweatshirts to your wardrobe? Check out these additional styles.