When to Wear a Sweatshirt

Go for a vintage-inspired marled grey sweatshirt like Rashida Jones.

Photo: Frederick M. Brown/Getty Images Entertainment/Getty Images

Until recently, you've thought of sweatshirts as the article of clothing you add puff-paint to and wear over leggings when you're eight ... or the keeps-me-warm-on-the-way-into-the-gym accessory. Though the term sweatshirt brings to mind super-casual circumstances, you'll be happy to know that the trend tides have turned in your favor. With newer designs and aesthetics, this comfy wardrobe staple works really well in a variety of daytime looks.

Vintage Sweatshirt

You've found yourself an amazing, fitted sweatshirt a la 1970s velour tracksuits. Well ... yours isn't velour, but you sort of wish it was. Already boasting a super-cool I-found-this-at-the-thrift-store-before-you-did appearance, you're already the envy of many an onlooker. Pull on some high-waisted slim jeans to keep the look a bit retro and slip into some flat sandals. Your casual, urban look is perfect for coffee with friends on an ideal weather day or a long afternoon in the park with your favorite book.

Boxy Raglan

When you would usually wear an oversized T-shirt to complete your undone-yet-chic outfit, you yawn thinking about wearing another cotton tee. Opt instead for a sportif edge by reaching for a boxy raglan sweatshirt. Look for something with a banded hem that falls near the waist and a 3/4-length sleeve to give this otherwise roomy top a shrunken appearance. Wear over rolled-up boyfriend jeans and wedges or your favorite pumps for a rough-and-tumble meets feminine style.

Thin Sweatshirt

Since you usually dress more on the classic side, too much edginess just doesn't play into your clean, straight-lined look. Shop for a thin sweatshirt that appears less '70s-athletic and more like a stylized long-sleeve T-shirt. Whether you wear it on its own with your favorite bootcut jeans or layer it over a thin T-shirt and a floral mini-skirt, a sweatshirt adds a soft, relaxed touch to your daytime outfit.


Dolman sleeves abound and you can't help noticing all of the slouchy looking, vintage-inspired sweatshirts that bring '80s Madonna videos to mind. Instead of buying a new one, washing it 50 times and trying to cut the collar off for off-the-shoulder magic, find a vintage-inspired one that's ready to wear. To keep a vintage appearance, look for not-so-saturated hues such as grey or faded navy. Throw this on over skinny jeans or pants or, if you find a tunic-length sweatshirt, wear it over black leggings. Very ballet-inspired feminine.

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