My Honest Take on the Winter It Boots Every Fashion Person Is Talking About

As the temperatures drop and the days get shorter, many of us cope by shopping for fresh pieces to add to our collections—whether it's a cozy cashmere scarf, a heavy wool coat, colored leather gloves, or the perfect pair of boots for various cold-weather outfits. Winter has its way of pushing even the most disciplined shoppers to indulge in a new seasonal wardrobe.

While there's a lot to browse, today we're focusing on women's boots, specifically the It boots that insiders are buzzing about behind the scenes. These are the pairs that fashion people are coveting, debating, and sharing links to in secret Slack channels, with paid Substack subscribers, or discreetly with a select group of loyal followers through Instagram broadcast channels.

While I may not be part of most private chats, as a fashion editor, I have a lot of insider intel about the It boots for 2025. This makes me an expert in the field. But don't worry, I'm not gatekeeping them. Instead, I compiled a list and visited various designer stores and department stores in NYC—from Toteme to Khaite and Nordstrom to Saks—to try on each style and give an honest review of whether they're worth your time and money. I considered not only size and color options but also comfort, versatility, and which styles pair best with jeans and trousers, as well as long dresses and skirts. With that said, keep scrolling to hear my thoughts on the must-have boots for fall and winter 2025 and shop them as you go.

The It Boots for Winter 2025

I've always been a big shoe person, so over the years, I've seen my fair share of styles; however, I have to say, this croc-embossed ankle boot from Toteme might just be one of the most elegant pairs I've ever come across. Croc-embossed leather is really having a moment right now, making its way into everything from handbags to outerwear and, of course, footwear, and Toteme has nailed it. The brand has taken a classic flat ankle boot silhouette and elevated it with this stunning crocodile print. While the color is technically chocolate brown, the subtle hints of black and beige woven into the pattern give it the perfect versatility, making it a neutral that pairs well with any outfit. The style is also very comfortable, especially around the ankle, where the leather is soft rather than stiff, and the design is roomy. For a sophisticated designer shoe like this, being under $1000 is a win in my book.

Size range: 35–42

Colorways: One

Sizing tip: Runs true to size

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It wouldn't be an It boot roundup without a pair from Khaite. Every fall, the New York-based ready-to-wear brand unveils a lineup of stunning boots, and while they're all undeniably elegant, there are usually one or two styles that capture that elusive It factor (think the Nevada and the Arizona). For fall/winter 2025, the Sybil boot holds that title. This style is almost sold out everywhere—and for good reason. It can only be described in three words: sculptural, hot, and sleek. Its distinct contoured heel flows seamlessly into the silhouette, complemented by a hidden zipper and the elongated pointe toe that Khaite has perfected. The glossy patent leather finish elevates the boot even further, and it's crafted from vegetable-tanned leather that will develop a natural patina over time for a rich, lived-in look. While the Sybil runs true to size, its narrow fit and tighter ankle mean that going up a half size may be ideal for those who prefer wearing thick socks and like more room.

Size range: 35–42

Colorways: Three

Tips: Runs true to size

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Staud's Wally Boots, ranging from ankle to knee-high designs, have been popular for many seasons; however, in 2025, fashion people are especially craving the knee-high style in snakeskin. Yes, the pattern is very trendy this year, and while not all designers have nailed it, Staud has.

When it comes to the silhouette, this knee-high style is a versatile choice. It can peek out below tailored trousers, complement your favorite mini skirt and tights for a night out, or tuck into your go-to jeans. But it's not just the knee-high design that makes these so desirable. It's also because that kitten heel has just enough height to boost your stature while keeping you comfortable all day. Plus, the elongated square toe adds a modern and sophisticated touch.

Size range: 35–42

Colorways: 19

Sizing tip: Runs narrow but true to size

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Another knee-high boot that's a bit more casual than The Wally is Vagabond's Kelsey boots. I'd say this style falls somewhere between a riding and a western boot. It has a polished look with a pointed toe and a high-low shaft design—higher on the outside of the calf and lower on the inside. Despite having a heel, they're comfortable enough to wear all day. I've walked in them for over 10K steps and could have gone longer. This is a pair I own and often choose when I want something easy to wear—with a minidress or when dressing up leggings and a sweater. I'll even tuck slightly-baggy jeans into them for that effortless cool-girl look.

Size range: 5–12

Colorways: Two

Sizing tip: Runs true to size

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I always like to highlight different brands in my stories, but Toteme's winter boot selection is so impressive that I had to include a second pair here. This style features a sock-like fit around the ankle, a sleek pointed toe, and a curved heel that sits closer to the middle of the shoe rather than at the back, as most do. Before trying the pair on, my sales associate warned me that the unique heel design might feel weird and different on the foot at first—and she was right. It's hard to explain the feeling until you put them on, but they did take some time to get used to as I walked around the store. However, it wouldn't be enough to hinder me from buying them, as my feet and ankles still felt stable and supported. I also want to point out that despite these not having a zipper, they're extremely easy to slip on and off. The 100% lamb leather is very supple and flexible. If you're looking for an ankle boot to wear with jeans or trousers, something that's a bit more sophisticated and will give you height, these are for you.

Size range: 5–11

Colorways: Five

Sizing tip: Runs true to size

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I've been saying this for a while now: Free People's We The Free boot selection is seriously underrated, and I'm not the only one who has noticed this. For example, I saw the Blaze Pull-On Boots online, and they immediately caught my eye because of their western-inspired design, with white contrast stitching and subtle distressing on the heels and toes. I also loved how they were a bit more casual and came up about 5 inches below the knee, making them perfect to pair with midi or maxi dresses and skirts. When I received them in the mail, I was excited because they looked just as good in person as online. I thought I might be the only one with them, but I was wrong. The following week, at a work event, I spotted a well-known fashion influencer wearing the same pair. I wasn't disappointed; it just confirmed my good taste. Since then, I've seen them more frequently on the streets of NYC and on my Instagram feed, establishing them as a must-have boot of the season.

Size range: 6–11

Colorways: Nine

Sizing tip: Runs narrow but true to size

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Shop More Chic Boots for Winter

Why Trust Us

At Who What Wear, fashion is our speciality. Our editors have years of industry experience, from reporting on seasonal fashion trends seen at international fashion weeks to working with some of the most recognizable names in fashion. Every item we recommend is carefully selected based on current trends, quality, and real-world wearability.

We regularly try pieces ourselves, including everything from bestselling jeans to designer shoes, speak to external experts and fashion insiders, and stay closely connected to what our readers are searching for. Our advice is grounded in expertise and has to pass our exceptional taste levels—so you can feel confident in every recommendation.