By 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.
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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.
The Everygirl
Crewneck Sweatshirt
Amazon | 47
Yankees Baseball Cap
Longchamp
Travel Bag
8 colors available
Sam Edelman
Leather ‘Sylvia’ Boots
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.
Free People
Faux-Fur Peacoat
2 colors available
Bloomingdale’s
Cashmere Midi Skirt
2 colors available
Madewell
Patent Leather Bag
3 colors available
Converse
Run Star Trainers
12 colors available
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.
Babaton
Fitted Blazer
10 colors available
Ann Taylor
Fitted Jacket
Madewell
‘Vernon’ Loafers
Anthropologie
Swirled Square Post Earrings
2 colors available
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.
Hyacinth House
Tweed Knox Shorts
J.Crew
Long Faux-Leather Trousers
SHEERTEX
Sheer Tights
Sam Edelman
Leather Ballet Flats
7 colors available
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.
Free People
Henley
9 colors available
Madewell
Ribbed Long-Sleeve Tee
4 colors available
Maeve
Faux-Suede Trucker Jacket
Abercrombie & Fitch
Tailored Wide-Leg Pants
10 colors available
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.
Levi’s
Western Shirt
2 colors available
J.Crew
Oversized Shirt
2 colors available
GAP
Trench Coat
2 colors available
GAP
Suede Slouchy Tote Bag
2 colors available
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.
SPANX
Wrap Mini Skort
4 colors available
Reformation
Relaxed Mini Skirt
5 colors available
Sam Edelman
Leather Loafers
11 colors available
J.Crew
Hinge Cuff Bracelet
2 colors available
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.
Pilcro
Oversized Faux Leather Jacket
Urban Outfitters
Faux-Leather Jacket
5 colors available
Abercrombie & Fitch
Tailored Wide-Leg Pants
10 colors available
Madewell
Multi-Keeper Belt
2 colors available
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.
Damson Madder
Shirred Midi Dress
Conditions Apply
Slip Midi Dress
4 colors available
Mango
Fringed Wool-Blend Scarf
4 colors available
ASOS
Fluffy Tassel Scarf
6 colors available
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.”
Quince
Italian Wool Coat
7 colors available
Eloquii
Striped Track Pants
3 colors available
Lucky Brand
Track Pants
Madewell
Leather Crossbody Bag
