Forget Footwear Fads—You’ll Always Find These 7 Classic Boots in Every Fashion Person’s Wardrobe

Okay, a quick hands up. How many among us own a pair of black leather boots? I'm guessing (without even having to see you) that the answer is just about everyone reading this. Sure, we've flirted with mesh ballet pumps, Mary Janes, kitten heels and enough slingbacks to last a lifetime, but when it comes to something reliable that you know will serve you well in any weather, a pair of classic, timeless boots are guaranteed to go with nearly everything in your wardrobe. Of course, there's more to winter than just plain black boots (and I happen to have my eye on a pair of brown suede ankle boots for the coming cold snap), but whether you're styling up a knee high or keeping it casual in a biker boot, there are a handful of key styles that never go out of style, making them a very wise investment for the long term.

We all want the same things from a cold-weather classic: comfortable, practical, versatile, and of course, stylish, and while we all have a pair of thick-tread boots tucked away for the really bad weather, there's no harm in looking for something elegant for work, the weekend, and all of your social plans too. So, which are the best anti-trend boots to elevate your winter outfits? You might not be surprised by the below six styles that fashion insiders wear on rotation, but you will agree that they are considered shoe staples for a good reason. Keep scrolling to see our pick of the best and to shop the latest styles. Enjoy!

7 Classic Boot Styles You'll Find In Every Fashion Persons Wardrobe this Winter:

1. Knee High Boots

Style Notes: Let's start as we mean to go on, with a boot so elegant that it makes every look exponentially better—it has to be, the knee high. Patent and pointed, soft suede or matte leather, no matter which style you choose, they always make the wearer look expensive. Tucking in a legging or a skinny jean has always suited the tall boot, but with 2024's boho revival still in full swing, expect to see a lot more of the maxi dress and knee high boot pairing this winter, it's the easiest way to do effortless chic.

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2. Chelsea Boots

Style Notes: It's difficult to pinpoint the exact moment that thick soled Chelsea boots re-entered our collective fashion conscious, but i have a sneaking suspicion that The Row's zip-up boots had a lot to do with it. Our appetite for chunky boots hasn't waned since, and if you're looking for a waterproof shoe that will comfortably go the distance, there's no better option, there's no better option than this.

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3. Ankle Boots

Style Notes: Continuing with short boots, the dressy alternative to the Chelsea boot is the ultra-refined heeled ankle boot. Perfect for pairing with wide-leg jeans and tailoring, this desk-to-dinner shoe is our favourite option for combining polish with pull-on-and-go ease, and with kitten and block heels being the current look du jour, they're easier on your feet than their look might suggest.

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4. Moto Boots

Style Notes: The new kid on the block is the moto boot, a clompy, stompy, buckled biker boot that proved its worth during festival season but shows no signs of slowing down for autumn/winter. Although it's obvious companion is the biker jacket, we've been inspired by it's summer styling (think prairie dresses and mini skirts), but to make it more seasonally appropriate, you can't go wrong with a chunky knit and denim.

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5. Over the Knee Boots

Style Notes: Take tall boots to new heights with the over-the-knee boot, the most impactful boot on the list. Not only do they look incredible, but they'll keep you warm too, and with so much of your lower half covered, you won't have to worry too much about outfit building—the shoe is clearly the star of the show.

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6. Cowboy Boots

Style Notes: It has to be said that some shoe trends can feel harder to style than others: enter the cowboy boot. If you're not into copious amounts of denim and flannel shirts these Western-inspired shoes might not feel like the obvious choice, but cowboy boots have enough unexpected lasting power to rival the plain black boot, and with the right look can be the point of interest that even the most pared back outfit can benefit from. Take inspiration from Karina [pictured above] and wear this statement boot with a slip dress and maxi coat to full effect.

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7. Riding Boots

Style Notes: Arguably my most-worn winter boot, the riding boot is no longer just for weekends in the countryside. These equestrian-inspired boots are actually incredibly easy to style. Not only can you style them with the usual leggings, maxi skirts and knitted dresses that you opt for in winter, riding boots can also help you to get more wear out of the mini skirts and dresses you would usually only pull out in the summertime.

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