10 Winter Outfits to Wear This Season

Every year without fail, once mid-November hits, my penchant for throwing on jeans and a sweater day after day suddenly loses its appeal. The staple duo I couldn’t wait to jump into at the beginning of the season no longer feels as exciting as it did just a couple months back. My trusty stockpile of denim? My carefully curated stack of knits? They’re no longer the fuel that drives me to jump out of bed on a chilly winter morning.

But there’s a reason we all gravitate toward these two cold-weather essentials. Together, they make for an easy, comfortable, fail-safe formula to rely on throughout the chilliest days of the year. Luckily, though, putting your winter safety net on pause doesn’t mean giving up all of your go-to comfortable outfits. If you, too, have been feeling less than inspired by your usual jeans-and-a-sweater combinations, then it may be time to give your cold-weather defaults the much-needed break they deserve.

Whether trading your cozy knits for statement outerwear or swapping your staple jeans for tailored trousers, there are plenty of comfortable outfit combos to explore this season that are a little more inspired. Ahead, I’m sharing 10 winter outfits to get you through your next wardrobe slump.

10 Winter Outfits That Aren’t Jeans and a Sweater

1. Leggings and a Sweatshirt

Lately, I’ve been into dressing up my leggings. Just when I thought I had the concept nailed, I came across this image and realized that I have a bit more room to grow. As a knee-high boot enthusiast, I’m shocked that I’ve yet to style them with a pair of leggings. But it doesn’t just stop there: The oversized tote, ball cap, and coat in this look work to level up the otherwise casual sweatshirt and leggings.

2. A Fur Jacket and Maxi Skirt

As if I needed any more reason to yearn for a fur jacket this season, this outfit just sealed the deal. Can’t be bothered to find the right top? No worries. In this look, the jacket is the top. And with the laid-back accessories, like the coordinating ball cap and sneakers, it’s the evidence needed to prove that yes, you can wear your festive fur far beyond the holidays.

3. Loafers and a Fitted Blazer

By now, I’m sure you’ve noticed the increase in fitted blazers across your For You Page. The trend was solidified earlier this season, and continues to rise in popularity as a welcome reprieve from the oversized styles of late. When styling, you’ll find that the dramatized silhouette does most of the work for you—just add a few accessories and a luxe pair of flats or loafers.

4. Tights and a Pair of Shorts

Before you write this look off entirely, just know that it’s a lot more practical than you think. In fact, I’ve worn more shorts this season than I have pants. The main reason being that I wasn’t quite ready to swap my summer favs, but also because it gives me all the more reason to wear my knee-high boots on a consistent basis. Paring your shorts with tights and/or boots is the unexpected combo that warrants a few head-turns, but still keeps you comfortable throughout the day.

5. Trousers and a Henley

As a stylist, something I have to remind clients of is the power of a simple tee. On the days when finding the right top becomes too difficult of a feat (or you’re sick of wearing sweaters), opt for a high-quality tee. In the colder months, I swap my usual short-sleeve crewnecks for more insulated long-sleeves—Henleys included.

6. A Button-Down and Trench Coat

No matter the season, a healthy stock of button-downs is a must. Wear them over a swimsuit, in place of a jacket, or layered under your favorite sweater—the styling possibilities are endless. But for the purpose of today’s dilemma, I find that one can never go wrong with a simple tuck of a button-down layered underneath a traditional piece of outerwear. Bonus points for a coordinating denim-on-denim ensemble.

7. Tights and a Mini Skirt

Personally speaking, the quickest way to get over a winter wardrobe woe is to throw on a mini skirt and tights. Walking through my Manhattan neighborhood in this little number was the confidence boost I needed to tackle the rest of the season with vigor.

8. Trousers and a Leather Jacket

In my opinion, it doesn’t get more classic than this. Trousers—a style once exclusively reserved for the workplace—are now the it-girl pants of choice, seamlessly taking the place of our everyday denim. In the same vein of leaning away from the workwear aesthetic, try going for something unexpected up top, like this leather jacket.

9. A Summer Dress and Chunky Scarf

Since saving this outfit last week, I’ve been actively trying to forget it. Update: I can’t. So excuse me while I scour the internet for a sheer coat. However, the key takeaway here is the art of winterizing your summer staples. Just know that the next time you see me, I’ll be sporting a midi dress with a chunky scarf—cute dog included.

10. Track Pants and a Wool Coat

Track pants—an unexpected trend this season—have slowly taken the place of our usual elastic-waist, satin pants this time of year. Although they still offer the same versatility as a silk pair, the striped add-on gives the look a sudden dose of it-girl energy. Whether you’re in the fashion crowd or not, sporting a pair of these buzz-worthy bottoms screams, “look out, world, I’m with them.”

ABOUT THE AUTHOR

Tinsley Crisp, Fashion & Beauty Staff Writer

Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.