7 "Chill" But Cute Outfits to Wear While You're Home for the Holidays
Listen, I'm not trying to imply that you still care what your high school archnemesis thinks of you anymore. HOWEVER, in case you do, there's nothing like a chill-but-cute outfit that suggests you barely tried but still look amazing to really put her jealousy over the edge—just sayin'.
And even if there aren't any ulterior motives involved, it’s always nice to have an arsenal of easy outfit ideas to wear when you’re home for the holidays… That way all you really have to think about is how many of your favorite spots you’ll get to eat at while still finding time to see all your relatives and friends (the ones you actually like).
That’s where I come in: Today I’ve found seven cool combos that promise all of the above and more, using pieces you likely to already own. To see for yourself and shop them along the way (because there’s always room for one more sweater), just keep scrolling.
1. Stylish Sweater + Jeans
The fashion sweater says I know what's trendy, while the jeans say I can keep it casual.
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2. Puffer + Jeans + Snake Boots
Polished snake-print boots are the perfect complement to the streetwear-inspired puffer.
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3. Sweatsuit + Sneakers
Sweatpants alone may not do much for your look, but throw in a matching sweatshirt and you suddenly have yourself a really cool outfit.
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4. Pajama Set + Mules
Roll out of bed and onto the streets in style with a chic PJ set and low-heeled mules.
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5. Oversized Cardigan + Loose Trousers + Boots
This combination is especially effective when you stick to a neutral palette.
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6. Turtleneck + Midi Skirt + Boots
When you want to look just the slightest bit dressed up but still "chill."
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7. Sweater + Slacks + Sneakers
Last but certainly not least, pair your work slacks with your favorite sweater-and-sneaker combo for an unexpectedly polished look.
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Next: Seven things that are probably taking up way too much of your closet space.
Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.
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