Feeling the Chill? Shop Our Editors’ Favorite Winter Fashion Finds

A collage of winter clothing items.

Katie Couric Media

Who says cold-weather clothes can’t be chic?

As we step into the frosty holiday season, embracing change is key to surviving the dark, cold times ahead — as is full-coverage clothing. The weather does a total 180 from those record high temps of the summer; daylight becomes precious when the skies begin to darken at 4 p.m.; and we must adjust our makeup and hair care routines for drier conditions. All of this calls for a positive attitude and lots of layers. 

While you may have your go-to seasonal sweaters all in order, there’s a chance your trusty boots have given out. Or your favorite maxi dress has a hole in the exact wrong place. Or you’ve spent years wearing a bulky jacket that just never felt right. Whatever the case may be, we all need to fill holes in our wardrobes sometimes. And if you don’t know where to start, we tapped a reputable source for all of your winter fashion needs: Our staff.

As editors from a wide variety of backgrounds, we like to think that we have pretty diverse tastes in what winter wear requires. With that in mind, we’ve gathered glowing recommendations for all things comfy layers, long sleeves, and trendy boots. After this read, you’ll be perfectly equipped for everything from a snowball fight to your office holiday soiree.

Free People Dolman Quilted Knit Jacket

Free People

“I first heard about this celebrity-favorite jacket from coworkers this summer, and if you checked my search history, you’d see that I looked it up about once a week in the months after that to pine. After a few months, I finally took the plunge and ordered it in red. Needless to say, I’m even more obsessed with it now that I have it: It’s heavy, blanket-like, and very soft to the touch, and I can already tell the 100 percent cotton fabric will age well. I ordered one size up from my usual, which probably wasn’t entirely necessary, but I love how oversized it is and I know I’ll be able to wear my bulkiest sweater under it without any issues.” — Ciara Hopkinson, Senior Associate, Account Management

$198 at Free People

PUMIEY Long Sleeve Maxi Dress

Amazon

“If you’re a TikTok fanatic like me, this piece likely looks familiar. It went viral this year, after all, for being a near-replica of the Skims long-sleeve dress. With my wallet in mind, I took a chance on this dupe and it absolutely delivered. I’m typically picky when it comes to tight frocks (as many of us are), but I’m mesmerized by the seemingly universally flattering fit of this dress. The length subtly elongates me and the soft, stretchy material doesn’t constrain me when I move. There’s no overheating (though the long sleeves keep me warm and toasty) or itching, and I get a boost of confidence with every compliment. One note: You can’t wear a bra with this piece unless you want a strap showing. If you crave some coverage, I’d recommend a strapless sticky bra or some trusty boob tape.” — Diana Valenzuela, Assistant Editor 

$37 at Amazon

Alo Muse Hoodie in Navy

Alo

“I’d been waiting for the viral athleisure brand Alo to drop a collection in a crisp navy color and they finally did this fall. When it launched, most of the items sold out, but now they’re (thankfully) back in stock due to the high demand. Navy’s a safe alternative when I feel the urge to move away from my mostly black workout gear. I love this Muse hoodie (which has a matching pair of sweatpants) — it’s replaced a few ratty old sweatshirts I tend to wear around the house.” — Alaina Mancini, Managing Editor, Branded Content

$108 at Alo

Free People Quinn Quilted Puffer Vest

Free People

I was searching for a slightly loose but still flattering puffer vest to wear on morning walks with my pup and to and from the gym when I finally laid eyes on this Free People option. It’s not easy to find something roomy that doesn’t swallow you whole, but this vest does it all. It comes in over 12 gorgeous hues (I opted for the sunny pink color) and each pairs seamlessly with a long-sleeved tee and leggings. It’s even roomy enough to fit a sweater underneath.”  — Alaina Mancini, Managing Editor, Branded Content

$128 at Free People

Alex Mill Neill Straight Leg Corduroy Pants

Alex Mill

“The second the first leaf hits the ground I’m pulling these babies out of my dresser. These pants are heavy enough to keep me warm on chilly days, but they’re slightly cropped, so they offer a little ventilation around the ankle. What really sold me on these is the adjustable waist, which is perfect for those who have to size up in pants to have them fit in the thigh and booty area. I personally went up two sizes from my normal in these for that reason, so the buttons on the waist are a lifesaver.” — Katie Pittman, Commerce Editor

$155 at Alex Mill

Trina Turk Coney Island Top

Trina Turk

“With the holidays right around the corner, I’m already dreaming of the sparkly outfits I’ll wear. This top from Trina Turk is shimmery but not too glittery, and I’m so excited to wear it with wide-leg trousers to our work holiday party or with a slinky slip skirt to dinners with friends. Maybe I’ll even go wild and wear it with jeans on a regular ol’ Tuesday or something. Clearly I lead an action-packed life.” — Katie Pittman, Commerce Editor 

$168 at Trina Turk

Thursday Knockout Chelsea Boots

Thursday Boots

“The worst feeling is having wet feet in the fall or winter, but most weatherproof shoes look (to be diplomatic) utilitarian. These boots from Thursday are cute as heck. I bought them over three years ago, and they’re still in near-perfect condition. The black matte color goes with everything. The boots come in different heel-heights, but I went for the highest so they’re a little dressier. Even with the height, they’re the comfiest non-sneakers I own. I wear them about three times a week, and I can personally attest that they stay dry in both snow and rain. They look awesome with jeans, dresses, or with slouchy socks under a skirt. I cannot recommend them enough.” — Emily Pinto, Senior Producer  

$168 at Thursday Boot Co.

Joe’s High Rise Wide Leg Mia Jeans

Joe’s Jeans

“After years of searching, I found the unicorn of jeans. They’re so comfortable and flattering that I can’t stop looking at myself in the mirror when I have them on. They’re stretchy so they hug your curves without getting loose throughout the day, and the dark wash is a fit for the dark days of winter. The cut and flare makes me feel taller, and when I wear them with brown boots with a small heel, they hit at exactly the right place so they don’t drag on the ground. They make me feel like a million bucks.” — Emily Pinto, Senior Producer

$218 at Joe’s Jeans

Summer Cap Sleeve Top

Amazon

“I know, I know, the name of this product has the word ‘summer’ in it, but it’s knit! Its versatility  is just one reason why I bought it in two colors with a third on the way…oops! Personally, I think cap sleeves are flattering for any body shape and I love how they’re cut just low enough so you can move around without feeling limited. Plus, they’re high enough so your bra straps stay hidden, and it makes for the perfect office top! For the colder months, I like to go up a size, layer a thin turtleneck underneath it, and winterize the heck out of it. This top comes in 12 colors — and at under $40, you can grab a neutral and a pop of color (the blue is gorgeous on any skin tone!) without feeling guilty of overspending.” — Meredith Struewing, Social Media Producer

$35 at Amazon

Veelo Casual Boot

Dirty Laundry

“One of my favorite trends of 2023 has been the lug sole. Characterized by that chunky, rubber platform heel, a lug sole can be gloriously versatile — they don’t look out of place in the office, but they’re ready for happy hour, too. As the weather has gotten good and frosty, this knee-high boot has been my go-to shoe for pulling any outfit together while still giving me winter-ready coverage. The stretchy upper is comfy (but doesn’t sag), the heel gives me some lift but doesn’t overwhelm me (I have graduated from being a stiletto girlie), and the black shade pairs with everything in my wardrobe.” — Diana Valenzuela, Assistant Editor 

$100 at Dirty Laundry

Amazon Essentials Long-Sleeve Henley Shirt

Amazon

“To me, nothing screams ‘winter’ like a long-sleeved henley shirt. While I originally bought this one for my fiance, it’s safe to say I’ve stolen it a number of times. Since it’s 100 percent cotton, it’s perfectly breathable, but it still keeps me (and him, I guess) warm. I personally like to layer it over black jeans for a casual dog walk or a not-too-fancy dinner outing. To be honest, he pretty much does the same.” — Diana Valenzuela, Assistant Editor 

$12 at Amazon

lululemon Belted Long Insulated Jacket

Lululemon

“I run hot, and I don’t spend a ton of time just hanging around outside in the winter — I’m not the most active winter athlete, you might say. When I’m outdoors in the cold, it’s usual to walk my dog or commute somewhere. So my winter coats tend to be a little thinner and not necessarily North Pole-ready. If you feel me, and you’re in the market for a new outer layer, look no further than this insulated jacket from lululemon. It’s not the heaviest or thickest winter coat but it keeps me warm without overheating when I move from office to subway to apartment this time of year. It’s also long and covers a lot of my body so it’s not just my torso that’s protected. What sold me was the open neckline: If you suffer from the winter sweaty neck, like me, you probably don’t own a lot of scarves. I carry one with me but I rarely wear it — you’ll more likely see me ferociously unzipping the top of my winter coat and airing out my chest on the subway platform (next time, say hi!), but thanks to this design, I’m not that girl anymore.” — Maggie Parker, Deputy Editor 

$150 at Lululemon