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.
Shop Knee High Boots:
The colour, the fabric, the detail!
Comfy chic.
Now these are a statement-making shoe.
The COS boot offering is exceptionally good this year.
The slouch effect adds laidback luxe.
Kitten-heel boots deserve just as much attention—especially when they look like this.
I can't help myself, these boots are just delicious.
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.
Shop Chelsea Boots:
Even Prada is in on the Chelsea boot game.
These will never fall out of favour.
Perfect for weekend walks in the country.
These would look great with blue denim.
How to get the designer look without splashing three figures.
This shade of brown is so premium.
I've already bought these for my sister and she swears by them.
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.
Shop Ankle Boots:
No one will believe that these are from the high street.
Believe me, these will go with everything.
Honestly, my dream shoe RN.
These are selling fast on the M&S website.
Let's not rule out the easy block heel!
Or this directional take.
A western inspired boots.
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.
Shop Moto Boots:
Bravo, Bershka, the archetypal biker boot.
I love this stripped back, minimalist take.
Burgundy makes everything look even better.
These could be mistaken for Isabel Marant.
The colour just makes these boots much better.
I'll always stand by a good Jimmy Choo boot.
Such a good find at H&M.
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.
Shop Over the Knee Boots:
Just add leggings and a long wool coat.
Be still my beating heart.
So good with mini skirts and dresses.
You can't argue with that price.
These are on my Christmas wish list.
I mean, come on, these look just like movie star shoes.
The OG over the knee boots have to be these Stuart Weitzman ones.
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.
Shop Cowboy Boots:
An influencer favourite.
A subtle nod to the western boot.
The black suede the perfect finishing touch.
Okay, this is a fashion forward boot I can get behind.
Such a chic iteration.
The colour, the material, everything is calling me in.
Ready to play the starring role in a western rom com.
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.
Shop Riding Boots:
I own these and they're so comfortable.
Minimalists will love these.
This brown shade is next on my wishlist.
Wear with leggings, skinny jeans or midi skirts.
The patent finish adds a fresh take to this pair.
Supremely elegant.
Simple, but so very effective.
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