3 New Ways to Wear Your Old Sweatshirts

Your collegiate self is gonna be stoked


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

Sweatshirts Man Repeller 11

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.

Get more Fashion ?
  • Devon Alexandra

    Long live the crewneck sweatshirt! Staple of my student wardrobe that makes me look like slightly less of a slob…

  • Camille Barron

    As evidenced by my blog name, I am always looking for ways to rewear things, so this article is right up my alley. Thanks for the tips & photos!


    Camille, a Nashville-based blogger

  • Harling Ross


  • I too am familiar with the sweatshirt/shorts/flops combo. Good times. Love these looks!

  • crln lr

    Sweeeeeet styling, great shots! 🙂

  • As evidenced by my blog name, I am always looking for ways to rewear things, so this article is right up my alley. Thanks for the tips & photos

  • Cristina

    1. How do all these spammers get real names? Can you please do an in depth look info creating spam accounts and how robots give them real names?
    2. Ummm… these old sweatshirts look nothing like my old sweatshirts but I could probably try my Gilmore Girls sweatshirt with some wide leg pants lol

    • Amelia Diamond

      they are also now getting VERY fun head shots. i just deleted one who was wearing ski goggles! love an athletic spammer.

  • Molly Weinberg

    I have been looking for those pink sunnies forever!! Definitely getting a pair!

    • Elizabeth Tamkin

      do you see the price? ace.

  • Barbara Mo

    you’ve probably heard this a million times but you’re such a diaamond when it comes to styling, Amelia.

    • Amelia Diamond

      i soak up compliments that involve last name puns like a sponge. i cannot get enough! thank you barbara mo 🙂

  • This should be five new ways to wear your old hoodies. I was just about to take my old sweatshirts out of the Donate pile but you have not succeeded in sparing them that fate.

  • Fashionably Sparkly

    Just got a pair of red lace pajama pants and I already know how I’m going to wear them… 😉 thank you!

    Fashionably Sparkly

  • Nicole

    hi guys/Amelia !! A couple months ago Leandra did a story in which she wore a sweatshirt tucked into a very small skirt & I asked her to share her sweatshirt-tucking secrets to which she asked if we would like a tutorial. Just wanted to throw that back into the mix by saying yes I really would still like a tutorial ✋✋

  • Jo Ho

    These outfits are ridiculous, who wears a corset over a sweatshirt, actually who wears a corset at all? Silly!