Simple and Stylish Outfit Formulas You Can Rely on All Winter

By Jordan Julian
Gap
Gap
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For a lot of people, the arrival of winter means the joy of the holiday season, the magic of a first snowfall, and the unparalleled comfort of snuggling up under a fuzzy blanket. But it also brings about a unique struggle when it comes to getting dressed each day — the age-old battle between warmth and style. If we could go back and give our younger selves one piece of advice, it would be to bring that jacket out, even if it might ruin an outfit. After all, nothing truly ruins an outfit like shivering and crossing your arms over it because you are turning into a human popsicle waiting to get into a bar. But we digress.

Luckily, Gap has an endless array of winter pieces that are equal parts comfortable and cute. Between trendy sherpa and luxe velour, you'll wonder why you ever dreaded getting dressed to go out in the cold. Below, we break down four foolproof outfit formulas that you can recycle all winter long. Staying warm has never looked so cool.

A Sweater and Coated Jeans
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A Sweater and Coated Jeans

The sleek, shiny appearance of the Gap Mid Rise Vintage Slim Coated Jeans ($80) adds an unexpected edge to classic denim. In other words, these bottoms look like super-flattering leather pants but feel like your comfiest skinny jeans. Pair them with a simple cozy sweater, like the Gap Cable Knit Sweater ($65). This is one of those outfit formulas that can be styled to work for most occasions — wear it with boots and a puffer for an everyday look, or heels and a wool duster coat for a fancy dinner.

A Sherpa Jacket and Relaxed Denim
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A Sherpa Jacket and Relaxed Denim

This 'fit is inspired by those effortlessly cool people you pass on the sidewalk and have to fight the urge to ask where they got, well, everything they're wearing. The centerpiece of the look is the Gap Oversized Sherpa Shirt Jacket ($148). Wear it with a fitted turtleneck, like this one ($40), and the Gap High Rise '90s Loose Jeans With Washwell ($70). Top it all off with a basic ribbed beanie ($25).

A Cozy Cardigan and Leggings
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A Cozy Cardigan and Leggings

This year, fashion was all about elevated loungewear, like the Gap Cozy Boucle Cardigan ($90). It's basically the softest robe ever, but you can absolutely wear it outside of your house. Keep the comfy theme going with the Gap Basic Leggings ($30) and shearling-style ankle boots ($55). This outfit is ideal for lounging or running errands, but it also works if you're headed to a workout class. Just throw the cardi over your favorite activewear set.

A Matching Sweat Set
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A Matching Sweat Set

Life's too short to worry about when and where it's appropriate to wear sweatpants. The answer? Anytime and anyplace you want, especially if you opt for an adorable matching set. We're currently obsessing over the Gap Velour Crewneck Sweatshirt ($50) and coordinating joggers ($50). You can wear this look with any jacket, but we're partial to the Gap 100% Recycled Relaxed Heavyweight Midi Puffer Coat ($198).