28 Cute Casual Winter Outfits

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Whether most of your winter days will be spent inside or you plan to venture out, you probably need something to wear besides sweatpants, PJs, and layers of outerwear. The good news is that you don’t need to buy many more basics than what’s already stocked in your closet to construct stylish, comfortable, and functional looks this season. Most of the outfits here consist of essentials such as live-in denim; tall boots; ribbed knits and sweater dresses; turtlenecks that work as the perfect foundation; and tights, a must-have outfit accoutrement this time of year. Piling on these simple pieces with a trendy coat you’ve invested in is really all you need to do before heading out the door.

If you need a travel outfit for a long drive, we’ve got your back — from cozy sweats to accessories like fuzzy bags and bucket hats. And if you just want to zhuzh up your walk-around-the-block attire, we’re here to offer subtle tips and tricks for making your outfit feel more considered, even on a bleak day when the effort is minimal. If you refuse to slip into a pair of rigid jeans this winter and you’re just trying to look cute in leggings, we promise it’s doable with the right puffer coat, a baseball cap, and a pair of cool lug-sole boots.

Ahead, determine which getups speak to your mood this winter — courtesy of some of our favorite industry creatives — then shop must-have items you’ll need to keep on hand to combat the crisp weather with similar poise.

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