sweaters

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Perhaps the only thing better than scarf season is sweater season. I mean, if you haven’t noticed, we kind of love sweaters here at The Gloss. Let’s just say it: sweaters are the perfect piece of clothing for fall. They keep you warm and cozy (honestly, some sweaters can feel like pajamas), and they’re still totally appropriate for pretty much any social or professional situation—you just have to style them the right way.

(Related: How to Dress Up Your Favorite Sweatshirt)

My favorite kind of sweater, by far, is of the oversized variety. I love feel like I could go into hibernation in my clothes if I needed to, and oversized sweaters allow me that option. The problem: even if you select the right size (which is, of course, key in selecting any piece of clothing), you still run the risk of looking like your sweater is swallowing you whole. But it doesn’t have to be like that! The right styling techniques can make even the bulkiest of sweaters look chic and street style-ready, and I can show you how to do it. For the purposes of this article, I’ve selected one sweater for all of my looks: the Island Ferry Dark Grey Sweater ($48) from Lulu*s. I’m a big fan of the low back on this one, but these looks for crewneck sweaters, too.

Read on to read our oversized sweater styling tips!

oversized sweater for work

If you’re going to wear something bulky to the office, you need to keep everything else neat, polished, and slim. Fitted ankle pants are always appropriate, and the print keeps things interesting without being too trendy. The heels keep the look from being too casual, and, of course, you can never go wrong with a bold (yet still understated, if that makes sense) statement necklace and structured, professional tote.

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oversized sweater for brunch

This is my absolute favorite thing to wear to hungover and/or boozy brunches on the weekends. It’s the easiest thing in the world to throw on a big sweater and a pair of jeans, and adding a long necklace and sheer lip tint keeps things looking polished.

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oversized sweater for a date

This, in my mind, is the ultimate cool-girl style. It’s not something I would have thought of on my own, but when I was in college, this is pretty much what every girl wore in the fall, and I absolutely adored the look. Dress it up for a date with stacked-heel boots (and tights if it’s cool outside!), a statement necklace, and some delicate rings. The best part? This look actually goes best with a messy ponytail or topknot, so you don’t even have to worry about styling your hair.

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oversized sweater for travel

I couldn’t make an oversized sweater style guide without including a travel section, because we all know that every girl in the world loves her sweaters and leggings at airports or for long car rides. The leather paneling on the leggings elevates the whole look, the backpack holds everything you need, and the scarf and tank tops are must-haves, because you never know if you’re going to get too hot or too cold while you’re traveling. Better to be safe than sorry, you know?

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