Key Takeaways
- This winter’s street style is all about stylish and wearable boots that can elevate any outfit
- Celebrities like Kendall Jenner, Rihanna, and Bella Hadid are rocking various boot styles, from pointed-toe booties to snakeskin stilettos
- Key boot trends include cozy shearling, sleek knee-highs, chunky lug-soles, and brown suede booties
- Patent finishes and animal print boots are also popular among celebrities like Taylor Swift and Jennifer Lawrence
- These boot styles can be paired with a variety of outfits, from minimalist basics to dressy ensembles
Introduction to Winter Boots
As winter soldiers on, having the right boots to face the elements is crucial. Thankfully, there are plenty of stylish options that can truly pull an outfit together. Celebrities like Kendall Jenner, Rihanna, and Bella Hadid are rocking various boot styles, from pointed-toe booties to snakeskin stilettos. These styles are not only chic but also wearable, making them perfect for everyday wear. Whether you’re looking for classics or trend-forward styles, there’s a boot out there to suit your personal style ethos.
Pointed-Toe Booties
Pointed-toe boots are almost a prerequisite to copying Kendall Jenner’s style. She’s been spotted many times this season, out and about in pointy styles, in everything from vintage Gucci to The Row. Pairing them with minimalist-friendly wardrobe basics, such as boot-cut jeans, T-shirts, and modern outerwear, is a fail-proof idea. This style is perfect for those who want to add a touch of sophistication to their outfit without going over the top. With its sleek design, pointed-toe booties can be dressed up or down, making them a versatile addition to any shoe wardrobe.
Cozy Shearling Boots
With freezing temperatures being the daily normal in the winter, Gigi Hadid knows the only way to truly keep your toes warm is in plush shearling boots. This New York-resident has been seen wearing many variations on this theme, mixing fur-trimmed boot silhouettes within her cashmere-heavy wardrobe. And though Gigi may be sporting hers on the streets of NYC, ones with a grippy tread and warm lining would complement any apres-ski wardrobe. Cozy shearling boots are perfect for those who want to stay warm and stylish during the cold winter months. With their soft and plush design, they can add a touch of luxury to any outfit.
Snakeskin Stilettos
One of fall/winter 2025’s biggest boot trends also happened to be Rihanna’s favorite. Heeled snakeskin boots that walked the runways were taken to the streets by Rih, who wore them with everything from billowy trench dresses to tailored suiting. Bold as they may seem, they’re really quite neutral—and therefore versatile enough to pair back to black, brown, and every color in between. Snakeskin stilettos are perfect for those who want to add a touch of glamour to their outfit. With their sleek design and bold print, they can elevate any ensemble from basic to bling.
Sleek Knee-Highs
Whether it be her ready-to-wear or accessory picks, Dakota Johnson relies heavily on the classics—and that includes black leather knee-high boots. Every shoe closet should include at least one pair, and below are a few of Vogue’s favorites. These streamlined shapes offer sleek styling capabilities with high reward—believe us, you’re going to wear these over and over, for years to come. Sleek knee-highs are perfect for those who want a timeless and versatile boot style. With their classic design, they can be paired with a variety of outfits, from dresses to trousers, and can be dressed up or down.
Chunky Lug-Soles
When Jennifer Lawrence takes to the streets, all eyes are on. This winter, she’s been giving black lug-sole boots plenty of play in her off-duty wardrobe, inspiring us to add a pair into our weekly rotation. Pair these modern Chelsea boots with everything from leather jackets and straight-leg jeans, à la Ms. Lawrence, to a flowy dress and topcoat for sensible flair. Chunky lug-soles are perfect for those who want to add a touch of edge to their outfit. With their rugged design, they can add a cool and casual vibe to any ensemble.
Brown Suede Booties
Brown suede has swept the fashion world, featured this season on everything from jackets to handbags, and, of course, boots. When shopping the trend, do it the Bella Hadid way—with a soft and sumptuous bootie shape in a warm tobacco hue. A little heel is all you need to dress up jeans, dresses, or tailoring, with a polished western attitude. Brown suede booties are perfect for those who want to add a touch of warmth and sophistication to their outfit. With their soft and sumptuous design, they can add a cozy and inviting vibe to any ensemble.
Patent Finishes
Leather, suede, or animal print—it’s no secret that Taylor Swift loves knee-high boots. Her go-to of late being a patent, block-heeled style, perfect for giving her various date night ensembles a little lift. She often styles them with a mini skirt, leaning into their mod-era roots, however, these would also look good with sweeping hemlines or even wide-leg trousers. Patent finishes are perfect for those who want to add a touch of glamour and sophistication to their outfit. With their sleek and shiny design, they can elevate any ensemble from basic to bling.