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5 Ways To Wear A Sweatshirt Without Looking Like A Slob



Ladies, I’m about to make some dreams come true. You know those days when you’re torn between your desire to wear sweats and your desire to look cute? Well, I’m going to fill you in on a trade secret: You can have it all.

Trendy hoodless sweatshirts are everywhere right now and while I’d never turn down a chance to wear this gem, the plain gray sweatshirt is sort of my jam. Why? Because there are so many fun ways to wear it and unlike the more bold takes on the sweatshirt trend, this one is really easy (and fun!) to dress up.

So sit back, relax and enjoy. I’m about to show you how you can wear a sweatshirt for your next night out at da club.

For class: Keep it simple. This weather is perfect for a lightweight sweatshirt paired with frayed denim shorts and some cute oxfords. The trick to avoid falling into the I-look-like-I-rolled-out-of-bed-and-went-straight-to-class trap is to resist the urge to wear sweatpants or leggings on the bottom.

For brunch: ¬†Add black skinny jeans and a black leather jacket if it’s not too warm outside. This is a great hangover outfit because it allows you to be comfortable and also tell the world you’re in a dark place. Booties – with a bit of a heel if you can handle that – are the ideal footwear here.

For a nice dinner: Layer your sweatshirt over a button-down – you can let the bottom of the shirt hang out below for a more undone look or you can tuck it in to be a bit more polished. Add either a pair of pants or a skirt, maybe a fun statement necklace and let your footwear take the look the appropriate level of dressiness – so heels are a good idea for a nicer restaurant, boots may be okay for something more casual.

For when you’re trying to be super trendy: Top off leather sweatpants or shorts with your gray sweatshirt – this will neutralize the look, plus the textures play off of each other in a really cool way. You can totally cop the downtown vibe if you pair these together. Cage sandals and a chunky necklace round out this look.

For a night out: Have you always wanted to wear a feather skirt but never had the guts? Why not try it with a gray sweatshirt? It’s a great way to make the skirt look a bit less over the top. Not into feathers? Try a tiered miniskirt or anything else that resembles a tutu. The key here is to temper a sort of crazy bottom with the ultra casual top. You can top off with a fun jeweled necklace and don’t get too crazy with your shoes.

    I'm a Chicago-based writer and graduate of the Medill School of Journalism who has written for sites like,,,,, Racked, Thrillist and The Huffington Post.