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Winter may be one of the trickiest seasons to dress for. Not only do you want to look stylish, but you also want to feel warm, which, in simpler terms, is a headache to figure out. And don’t even get me started on putting together an outfit when there’s an active snowstorm outside you have to trek into. As a lifelong New Yorker who’s endured the city’s harsh winter season, often characterized by a cocktail of more-than-miserable weather — Freezing temperatures! Blizzards! More slush puddles than you could ever imagine! — I’ve learned a thing or two about dressing and accessorizing for the elements. From durable designer bags ideal for holiday travel to iconic rubber boots that withstand even the wettest of winter storms, these picks are a must for creating a functional cold-weather wardrobe without sacrificing fashion.
Prices are accurate as of October 21, 2024. Subject to change.
For Toasty Layering: Uniqlo HeatTech T-Shirt
I’ve owned different styles of HeatTech through the years, but perhaps my favorite is this thin, long-sleeve pick that offers an extra layer of warmth without looking bulky. Not only does it keep you warm thanks to its heat absorption technology, but a combination of ultra-fine fibers and plant oil gives it a wonderfully smooth feel. This base layer is a must-have in the winter, especially if you enjoy outdoor activities like skiing or snowboarding.
A Popular Beanie: Carhartt Knit Cuffed Beanie
My first foray into Carhartt beanies was when I stole my boyfriend’s years ago and enlisted it as my winter headwear. Unsurprisingly, this hat is one of the most popular ones out there. It has a stretchy ribbed knit design, an extra-large folded cuff, and the iconic Carharrt logo sewn right on the front. The Carhartt beanie is also machine-washable, so you can throw it in with the rest of your laundry when it gets dirty.
A Chic and Warm Scarf: Quince Mongolian Cashmere Scarf
If you’re picky with scarves (there are just so many out there that are too lightweight or itchy), give this highly-rated Quince one a go. It’s made from 100% cashmere sourced from Mongolia and has a deliciously soft feel. It also boasts an extra-long length, which makes bundling up with it so easy — no scarves that skimp on size here. Available in nearly a dozen shades, it looks great looped around your neck or draped over your shoulders with wool coats, blazers, and fuzzy cardigans.
For Toting Your Things: Longchamp Le Pliage
If you buy one new bag this season, let it be the Longchamp Le Pliage. Not only is this bag timeless, but it is also spacious, durable, water-resistant, and made from recycled canvas, so it’s a match for holiday traveling and unexpected snow storms. I own the medium and large versions and interchangeably use both as a weekend bag for out-of-state car trips, a carry-on for plane rides, and a work tote (either size is big enough to fit a laptop). The best part? You can easily fold it into a small, lightweight, portable square, making it incredibly easy to pack in suitcases or store it when you aren’t using it.
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For Keeping Feet Dry: Hunter Rain Boots
An easy way to keep your feet dry and warm during the cold season is by picking up a pair of Hunter rain boots. Hunter, founded in 1856 by an American inventor in Scotland, has become synonymous with rainboots, and the brand has been my go-to since college. I’ve bought multiples of the original tall style (short is also available) — giving some as gifts — and they’ve held up over the years without tearing. They are 100% waterproof and constructed using only natural rubber. Wear these as-is or style them with a pair of the brand’s boot socks for an added layer of insulation.
Winter-Proof Leggings: Baleaf Fleece-Lined Leggings
Love leggings but hate wearing them outside during bad winter weather? Try a fleece-lined pair instead. Whether you’re a runner or just want cozier loungewear you can wear out, these bottoms will keep you so much warmer than traditional leggings. They have a waterproof finish, a high-waisted fit, two large thigh pockets, and a hidden waistband pocket ideal for your credit cards or keys. These are *chef’s kiss* styled with an oversized sweatshirt, slouchy socks, and a pair of Ugg boots.
For Texting During Below-Zero Temps: FZ Touchscreen Magic Gloves
Attempting to text outdoors during chilly weather is no fun. Thankfully, you can avoid frozen fingertips by ordering these touchscreen gloves equipped with a warm wool lining and a secure elastic cuff. The thumb, middle, and forefingers work on phones, tablets, and other touchscreens, allowing you to text, Google, scroll, and more, even during frigid temperatures.
Fuzzy Slippers For Indoors or Outdoors: Ugg Tasman Slippers
Ugg boots have been a staple in my wardrobe since I was a teenager — I saved up money junior year to buy a tall pair and wore them for nearly a decade before replacing them. I’m now ready to branch out from the traditional tall boots. The Tasman slippers are comfortable enough to lounge in all day around the house yet durable enough to throw on with cashmere socks (or a pair of Ugg socks) to run last-minute holiday errands. They boast a soft suede upper, cozy sheepskin lining, a pure wool insole, and a sturdy rubber outsole. Treat them with the brand’s biodegradable shoe protector spray to keep them looking like new.
When You Need Something Cozier Than Denim: Levi’s Corduroy Overalls
I added these to my fall and winter wardrobe last year and instantly noticed how much easier dressing for frosty days was, thanks to their thick, warm feel. They look great layered over long-sleeve shirts, cashmere turtlenecks, and simple white tees and can be worn right through spring. A bonus? Overalls also have a timeless silhouette that really never goes out of style.
To Keep You Warmer During Outdoor Winter Events: HotHands Hand Warmers
Although these hand warmers aren’t technically clothing, I do keep these in my jacket pockets when I’m outside during the colder months. They’re portable, made from natural materials, and provide up to 18 hours of heat. To activate, all you have to do is open the package and make sure the warmer is exposed to air. If you feel its heat is waning throughout use, just shake it to reactivate, and you should be good to go. I use these when I run errands around the city in the winter and find myself waiting at bus stops or subway stations longer than I’d like, but they also would work great for outdoor sporting events and camping.
Featured Image Credit: Pablo Merchán Montes/ Unsplash+
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