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Though we don’t get much icy weather here in Texas, I know lots of our winter calendars include a snowy getaway (or two). Whether it’s a visit to Aspen, New York, Montana, or beyond, every packing list and winter capsule wardrobe shares one non-negotiable: winter boots that are actually cute. And not just cute—waterproof, non-slip, and effortlessly stylish. Sporty works perfectly fine on the trails, but there’s something special about a pair that moves seamlessly from outdoor escapades to dinner reservations.
Consider this your guide to the best winter boots of the season—pairs built to handle the slush and snow, yet polished enough to wear long after everything starts to melt. Think warm insulation, durable waterproof materials, and grippy soles that just so happen to look beautifully chic.
The 10 Chicest Waterproof Boots
To make this list, these winter boots had to combine function with fashion, without skimping on either. Trust us, each pair will have you feeling confident walking on icy sidewalks and walking into dinner.
VARLEY
A refined take on the classic alpine boot, the Selva pairs plush shearling with a sturdy tread that keeps you grounded in slush and snow. It’s equal parts practical and polished—perfect for winter errands or après-ski drinks.
SOREL
Out N About Iv Chillz Waterproof Boots
These Sorel favorites are built for real weather, with waterproof construction and a cozy fleece lining that warms instantly. Sporty without feeling bulky, they’re ideal for days when function truly matters.
Stuart Weitzman
The Myla Bootie delivers winter luxury with its soft shearling trim and sleek silhouette that easily dresses up or down. Consider this your chicest companion for cold-weather city strolls.
Freda Salvador
Handcrafted and beautifully detailed, the Winnie offers a modern, minimalist silhouette elevated by subtle shearling lining. It’s the kind of investment boot you’ll wear for seasons to come.
Timberland
Stone Street Warm Lined Pull-On Boot
With warm lining, a substantial lug sole, and Timberland’s iconic durability, this pull-on boot brings easy, slip-in practicality to winter dressing. The rich brown leather looks especially good paired with denim or wool trousers.
VARLEY
The Calsen blends elevated design with everyday wearability—think streamlined suede, a modern lug sole, and just enough height for a subtle lift. Effortlessly chic, even in less-than-chic weather.
MOON BOOT
Playful, iconic, and surprisingly warm, these Moon Boots are a statement-maker in colder temps. Wear them when you want comfort without sacrificing personality.
Cougar
Lightweight, weather-ready, and incredibly warm, the Niloa is made for icy sidewalks and last-minute winter getaways. The minimalist profile also makes it easy to pair with everything in your suitcase.
Stuart Weitzman
This zip-up version of the Myla brings extra ease without losing an ounce of style. Sleek leather meets soft shearling for a boot that transitions seamlessly from daytime adventures to evening plans.
PENELOPE CHILVERS
True to its name, the Incredible Boot is handcrafted, hardwearing, and effortlessly elegant—designed for snowy escapes and long walks through the city. It’s a timeless choice for anyone who wants utility wrapped in understated luxury.
What to Wear with Winter Boots
Now that you’ve found a pair of winter boots that are actually cute, here comes the fun part: styling. Here are three outfit formulas that are just as trusty as your new boots, and will take you from adventure to aprés.
1. Oversized Sweater + Leggings + Chunky Socks
This formula works because it layers comfort and structure in just the right way—balancing the ease of leggings with the cozy volume of an oversized knit. Chunky socks peeking out from your boots add intentional texture while keeping you warm. To make the outfit feel elevated, stick to a monochrome palette or pair a neutral sweater with rich, wintry tones. Finish with a crossbody bag or long coat to pull everything together.
VARLEY
2. Slim-Fit Jeans + Printed Coat + Cashmere Neck Scarf
Slim-fit jeans create a clean base that lets your statement coat shine—this pairing always looks polished with winter boots, especially those with chunkier soles. The cashmere scarf adds warmth without bulk, grounding the entire look with soft texture. Choose a coat with a subtle pattern (think plaid or herringbone) to keep things chic, not overwhelming. A sleek boot silhouette will balance the proportions perfectly.
AGOLDE
Ralph Lauren
Brochu Walker
3. Fleece-Lined Tights + Sweater Dress + Duster Coat
This combination is a cold-weather classic because it layers warmth in a way that still feels streamlined and feminine. Fleece-lined tights keep you comfortable, while the sweater dress adds soft movement that pairs beautifully with taller or lug-sole boots. The duster coat elongates the body and gives the whole outfit a pulled-together feel. Opt for a tonal palette to make the look feel instantly luxe.
This post was last updated on November 22, 2025, to include new insights.
