3 New Ways to Wear Your Old Sweatshirts

I had to take a quick sweatshirt hiatus after college. Anything fleece-lined and hooded with a kangaroo pocket gave me a schlubby feeling. It reminded me of snooze buttons, laundry days, flip-flops and going-out tops. It reminded me of Uggs. Finals. Warm beer.

But, as with so many things in fashion, the (self-projected) stigma began to ease. Flip-flops, going-out tops and Uggs have all had recent, triumphant return, after all. Why not the most comfortable thing in my wardrobe? Hoods didn’t have to remind me of greasy-haired hangovers! In fact, hoods could inspire a whole new way of looking at my wardrobe — one that fits in perfectly with the cold-to-chilly-to-warm transition of spring.

Let’s Louie Vuitton-don a hoodie and get right into it.

Start With the Classic Combo: Sweatshirt + Shorts

Sweatshirts Man Repeller Feature

Topshop sweatshirt, Uniqlo shorts, Charlotte Olympia shoes, SUNGLASS.LA sunglasses

The sweatshirt/shorts combo brings me back to iced coffee and bagel runs during summer break (is that even what you call it anymore??). Back in the day, I would wear this mind-blowing combo with the aforementioned flops, further accessorized with oversize sunglasses, my Samsung Chocolate phone and my Saturn Vue car keys. I just really needed to bring you into that moment with me.

Anyway, to channel the youthful euphoria of running totally unnecessary errands just because you’re bored, try this: a turtleneck — because it’s still chilly — under a hoodie, with NON-DENIM shorts in a similar-but-clashing color scheme, and big old platform shoes for fun.

Next, Dress Up the Pajama Pants You Planned to Wear to Class

Sweatshirts Man Repeller 9

Champion sweatshirt, Yuliya Magdych skirt over Elizabeth and James pants, Gucci shoes

This one’s easy: pajama-like pants — but ones too pretty to actually sleep in, flatform shoes to avoid dirty-pant-pooling, a sweatshirt and a skirt that’s meant to be buttoned or, conversely, worn as a waist-cape. Bring sunglasses with you just in case you feel a lecture nap coming on; just explain you’re out of contacts and these are prescription.

Graduate With a Corset

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Tibi corset over American Apparel sweatshirt, Ulla Johnson pants, Gucci shoes, Jessica Biales rings

In the world of sweatshirt dressing, this is Advanced Placement — but you’ve been hand-selected. You’ve got this. The key: big, wide pants in khaki. They will keep the Kardashian korset/waist-training comparisons at bay. If you don’t even care, congratulations! That’s called Senioritis. You’ve got it bad, which means you, my friend, look wonderful.


Special thanks to our model Kira Shipway, follow her on Instagram @kiraship. Market assistance by Elizabeth Tamkin; photos by Seher Sikandar, check out her website here and follow her on Instagram @rehes.

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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