New York City Or Aspen: These Are The Boots Trendsetters Swear By

The vibe: Chanel in the streets, Merrell on the mountain.

Taylor Tomasi Hill
A mirror selfie of Taylor Tomasi Hill wearing leather sock boots by Chloe.

Style can so often outweigh practicality for fashion lovers, especially when it comes to cold-weather footwear. While trendy winter boots from heeled to ankle-baring and detailed designs can easily survive city sidewalks, car commutes, and wintry events, many aren’t suitable for chilly outdoor adventures. Think mountain getaways, winter hiking, or snowy cottage escapes where designs like snow boots and insulated hiking shoes become necessary. But, despite what some naysayers may tell you, muddy tones, goofy-feeling silhouettes, and weirdly grippy soles aren’t the only options out there when it comes to the best winter boots. Sensible design and elevated style not only can go hand in hand but abound if you know where to look.

For a more aesthetically pleasing winter boot collection, leave it to fashion insiders to scout the most stylish options out there that hold up to extreme winter weather. But, of course, for those day-to-day winter boots you crave with jeans and cozy knitwear, athleisure, and cold-weather dresses, style pros have a mountain of favorites. Ahead, discover 14 picks from fashion directors, designers, stylists, and brand experts, all of whom have great style and equally appreciate functional footwear for cold city days and frosty outdoor escapes.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Taylor Tomasi Hill, Creative & Fashion Director, The Yes

“Being from Dallas means outdoorsy is a relative term,” says Taylor Tomasi Hill, creative and fashion director of THE YES. “A boot that’s hiking-chic might only be made for hiking to brunch. That said, I have always loved a duck boot: classic, heeled, over-the-knee; you name it, I’ve worn it. You can go with a classic Sperry and call it a day, but that’s tough when you have beauties like Thom Browne calling your name. The investment makes sense when you wear them year after year.

I like to wear them casually with a cheerful Clare V. hoodie or cardigan from Kule, Bottega Veneta crossbody, and denim. (These new biodegradable jeans from FRAME are next-level sustainable.) Or go a little more fashion-forward by pairing back to an Alexander McQueen statement jacket and leggings. Anine Bing and Splits59 are among my favorites.”

“A boot...with a bonus sock?! I can’t resist, [from] the chunky knit sock, the rich leather, the perfectly pitched rubber sole,” Tomasi Hill tells TZR. “These Chloé boots with an après-ski vibe look at home in any city. I like to play off the coziness with a sweatpant — Tna by Aritzia makes a super affordable but chic pair — and dress it up a little with this artful RE/DONE vest. (It’s made from patched together upcycled sweaters, and I’m obsessed.) Toss on Machete glasses, a Kule baseball cap over your slept-in hair, and Bottega Veneta pouch for a great coffee and errands look.”

Aya Kanai, Head of Content & Creator Partnerships, Pinterest

“For outdoors, it’s always the Merrell Moab,” says Aya Kanai, head of content and creator partnerships at Pinterest. “It’s a classic style and so comfortable for a hike in the woods or selecting pumpkins with my family.” Try a high-top option to keep your ankles secure on your excursions.

“I wear R13 boots like it’s my job and to my job,” Kanai tells TZR of her go-to city style. “The stacked sole gives me some extra height. I know it’s not a traditionally ‘professional’ style, but to me, it’s put together enough for the office, hosting a panel discussion, going to events, all of my work needs.”

Lauren Harwell Godfrey, Jewelry Designer

“My favorite outdoorsy boot is the Blundstone Chelsea,” says jewelry designer Lauren Harwell Godfrey. “I live near wine country and learned about these from the winemakers who live in them in the vineyards. They’re super comfortable and can take a beating.”

As for something more fashion forward, “for the city, I love Balenciaga’s Blade boot for its edgy silhouette,” says Harwell Godfrey. “I love wearing them with a skirt, sweater, and coat. It adds a bit of sophisticated polish to any outfit.”

Divya Matur, Chief Merchandising Officer, Intermix

“I was just in Aspen, and Moon Boots are the perfect shoe to take you from the slopes to après ski — just tuck your ski pants in,” says Divya Matur, the chief merchandising officer at Intermix. “I love the Pillow Metallic Snow Boot in Rose Gold, paired back to black ski pants and a crisp white ski jacket. I always add a fun pop of color with a bright beanie.”

“For trekking through New York City in the winter, I love a combat boot,” Matur says. “There are so many amazing options this season, and one of my favorites is the Valentino Roman Stud. For daytime, I’m wearing them with an oversized sweater and leather leggings, and they work just as well at night styled with leather shorts and tights.”

Sari Tuschman, Senior Vice President, AETHER

“For snowy, wintery days in Colorado, where I live, my go-to’s are the Dolomite Boots,” Sari Tuschman, senior vice president of AETHER, tells TZR of the brand’s leather style. “They’re great-looking, but it’s the sturdy craftsmanship and Vibram soles that make them the ideal boot for inclement weather. It’s the perfect combo — I can still look put together but not slip on the ice.”

“For city boots, I live in my Chanel motorcycle boots,” says Tuschman. “They literally go with everything. They have a small heel and are sleek enough to dress up, but they’re also comfortable and versatile so, I can wear them all day and stay comfortable. I truly think I’ll wear them forever.”

Elizabeth Kanfer, Nordstrom Fashion Director

“This Moncler boot is both technical and transitional — perfect for hitting the trails and the city streets,” says Nordstrom fashion director Elizabeth Kanfer of the chunky-soled hiking boot from the beloved outdoors brand. “Wear with active hiking gear for outdoor escapes or shades of off-white and creams for a casual yet chic daytime look.”

“This Tory Burch boot looks great on any city streets,” Kanfer says. “Completely versatile, it can be paired with denim or knit dresses to ground the look.” Finish the look off with a long leather coat or a down option for especially cold days.

Julie O'Boyle-Sharp, Style Blogger

“For city or country, but especially country, there’s nothing more classic or comfortable than the six-inch classic moc from Red Wing Heritage,” says Portland, Maine-based style blogger Julie O’Boyle-Sharp. “I have them in Rose, which is an unexpected color in the sea of sensible black and brown here in Maine, and they look great with everything — dresses, work pants, boilersuits, jeans. I’ve worn mine to chop wood, on an apple-picking date, and for drinks downtown. That’s versatility. We’re in the thick of winter right now, so currently, I’m loving mine paired with vintage army pants, a mock-neck sweater, and a wool plaid jacket.”

“If I’m putting together a more polished look for a day in the city, I’ll reach for a pair of low-heeled Chelsea boots, like this pair from Ganni,” O’Boyle-Sharp says. “The sleek design pairs so well with dresses, especially midi-lengths, and the heel adds a little height while still being comfortable and cobblestone-friendly. I’d pair them with a ‘30s-inspired midi dress with a cropped sweater thrown over it and a quilted jacket. Cozy, easy, cute, and they look just as great with jeans and a sweater for more relaxed days.”