Although autumn hasn't quite arrived just yet (we're still denying the fact that's it for the great British summer) we're welcoming the return of socks and coats, jumpers and scarves with open arms. Ankle boots are the surest sign that the seasons are changing, and will easily become the hardest working item in your autumn/winter wardrobe. Contemplating the grown-up equivalent of a 'back-to-school' wardrobe? A reliable pair of boots is going to be your best friend. And whether you prefer something heeled or thick-soled, there are plenty of options in the ankle boot department.
For those who value versatility, a classic leather ankle boots are certainly an essential and will quickly become your best friend throughout the cooler months. Opt for a block heel for all-day comfort or a pointed toe for that extra touch of sophistication. If you're feeling like you want something different, experiment with textures - think suede, snake-print or even croc-embossed. These materials not only add a little more visual interest, but also a tactile richness that can elevate a simple look into something more extravagant.
The Best Ankle Boots For Women 2025, At A Glance
Best overall ankle boots: Dr Martens 1460 Soft Leather Lace Up Boots, £170 at Dr Martens
Best Chelsea ankle boots: R.M.Williams Comfort Lady Yearling Boot Chestnut, £425 at R.M.Williams
Best chunky ankle boots: GANNI Stitch Cleated Mid Chelsea Boots, £375 at GANNI
Best 'quiet luxury' ankle boots: Kurt Geiger Taken Carvela Boots, £169 at Kurt Geiger
Best cowboy ankle boots: Oliver Bonas Ecru Cream Leather Western Ankle Boots, £130 at Oliver Bonas
Best hiking ankle boots: Penelope Chilvers Brae Leather Boot, £233 at Penelope Chilvers
Best ankle boots for going out: & Other Stories Wide-Shaft Ankle Boots, £245 at & Other Stories
Best biker ankle boots: Russell & Bromley Angel Short Biker Boot, £295 at Russell & Bromley
Best value ankle boots: M&S Chelsea Flatform Ankle Boots, £35 at M&S
There really is a pair of ankle boots for every occasion, too and that's where the fun begins. For a casual day out, we would advise to style a pair of chunky Dr Martens or biker boots with relaxed denim and an oversized knit (depending on how cold it is). If you're heading to the office, a polished, heeled ankle boot will work wonders with a midi skirt or any smart tailoring, especially if it's a kitten heel. Alternatively, if you're out for the evening, a slim heel always looks so chic with a dress or wide-leg trousers.
We've rounded up the ankle boots we're relying on this transitional period, on top of our pre-existing pairs of knee high boots and thigh-high boots.
Shop: The Best Ankle Boots For Women 2025
Best overall ankle boots

www.drmartens.com
Dr Martens is just cult, and I feel like everyone's had their Dr Marten era, but I strongly believe we should still be in it. They're super easy to style and never get old - I've had mine years and years. The Dr Martens 1460 boots are a classic style that have been reimagined for maximum comfort. With the same rebellious edge the brand is known for, these boots feature a softer, more pliable leather for easier wear. The leather in question is called Virginia, and it's a soft, fine-grain leather that's treated to make it smooth and supple - so maybe you don't have to be armed with an array of plasters when you leave the house wearing these.
Pros
- Renowned brand for ankle boots
- Made from a soft, fine-grain leather for a comfortable fit
- Goodyear-welted lines are heat-sealed for durability
Cons
- Dr Martens usually require some serious breaking in
Best Chelsea ankle boots

www.rmwilliams.com
If there's ever a classic leather boot you can always rely on, it's from R.M.Williams. Handcrafted since 1932, the Australian cult-favourite brand knows how to create products that endure. Ranging from earthy mid-brown and chocolate hues to chestnut and black, they are a staple to have in the wardrobe, and are known to last a life-time. The Comfort Lady Yearling boot is a bestseller for R.M.Williams as they are the type of boot you can walk for hours in, and your feet will still feel better than ever. There are other popular boot styles with a slightly higher heel perfect for the evening but you can never go wrong with a Chelsea-styled boot for versatility and your first pair (because trust us when we say you'll be wanting more).
Pros
- Rubber sole brings hardy wearability
- Side elastic panels for a classic Chelsea boot look
- Available in a wide fit
Cons
- Majority of your Australian friends will own a pair (or two)
Best chunky ankle boots

www.ganni.com
Your new go-to pair of boots for this somewhat strange transitional period are the Chelsea boots from GANNI. With a sleek, smooth leather upper and cleated sole, these shoes are the perfect balance of edgy and practical. The towering rubber platform not only offers durability on those autumnal walks, but also adds a contemporary, rugged aesthetic that makes these boots a statement piece in any outfit. Featuring elastic side panels and a pull tab for ease, they embrace the classic Chelsea boot design, with more of a, let's say, GANNI twist.
Pros
- Unique toe cap details
- Chunky cleated soles
- Elongated side pull tabs
Cons
- These boots come up quite small
Best 'quiet luxury' ankle boots

www.kurtgeiger.com
Carvela's Chelsea is a great multi-tasker that you can wear with jeans or dresses, which you might find is particularly useful when the weather doesn't know whether it's summer or autumn. Crafted from leather, these boots boast a refined (or 'quiet luxury') silhouette while maintaining the robust practicality that Chelsea boots are known for. The subtle contrasting stitching around the sole (reminiscent to that of Dr Marten's) adds a hint of character, and the durable heel gives just the right amount of lift for all-day wear.
Pros
- Feature a small pull tab for easy on and off
- Black leather upper
- 'All day long' technology to keep your feet comfortable, well, everyday
Cons
- Not available in half sizes
Best cowboy ankle boots

www.oliverbonas.com
The motto I like to live by is if in doubt, add a cowboy boot. Trust me on this one. If you ever feel like your outfit is lacking something, add a pair of cowboy boots and you'll immediately feel cooler. I wore this pair from Oliver Bonas so much last year and I'm hoping to get lots of wear out of them this year, too. Plus, we're seeing no signs of the cowboy boot trend slowing down, again spotting them hundreds of times at the most recent Copenhagen Fashion Week. Featuring a sharp pointed toe and sturdy block heel, these boots are perfect for day-to-night transitions. During the day, style the western style boots with a floaty midi or maxi dress, and for the evening swap it for a mini dress and statement necklace.
Pros
- Block heel so you can wear all day and still feel comfortable
- On-trend Western style
Cons
- Cream isn't the most practical colour for this time of year
Best hiking ankle boots

penelopechilvers.com
A hiking boot is great for festivals, but also for everyday (when you have no intention of dancing in a muddy field or climbing a mountain, which is probably most of the time if we're being honest). If you're on the hunt for the most desirable walking boot in the business, Penelope Chilvers is the brand for you. This particular pair, the Brae Leather shearling boot, are fantastic for when the weather gets even colder and you might need to rely on some of the shearling inside the boot for extra warmth.
Pros
- Water resistant
- Fully lined with shearling
- Easy to wash/care for
Cons
- Slightly pricer
Best ankle boots for going out

www.stories.com
These boots are a throwback to the swinging sixties. With a sleek silhouette, kitten heels and a refined almond toe, these boots are the perfect combination of playful yet polished. Their very AW beige hue makes them a standout shoe, ideal for injecting a little colour (but not too much) into a neutral or all-white outfit, or complementing brighter looks.
Pros
- Made from smooth leather
- Manageable kitten heel
- Natural beige suede hue
Cons
- Some reviews say the leather is very hard
Best biker ankle boots

www.russellandbromley.co.uk
Russell & Bromley, in case you haven't heard, is a British fashion brand that specialises in luxury shoes and handbags. This pair are almost like a love letter to modern minimalism, blending elegance with edge. With a distressed leather finish that suggests both adventure and authenticity, they boast a standout gold buckle that adds an element of luxury to its tough exterior. Perfect for navigating city streets or countryside paths, its cleated sole provides both comfort and grip, making them as practical as they are stylish.
Pros
- Made from brown distressed leather
- Buckle strap detailing
- Cleated sole
Cons
- Sometimes can be difficult to get hold of due to popularity
Best value ankle boots

www.marksandspencer.com
Designed with a low heel and flatform sole, these boots offer a timeless look without compromising on wearability. The side panelling adds just a dash of attitude, while Marks & Spencer's innovative Insolia Flex technology makes sure that your feet are perfectly positioned while wearing the boot. Plus, with the Freshfeet antibacterial padding, you can say goodbye to any worries about odour. And, at under £40, what's not to love?
Pros
- Classic style
- Low heel
- Insolia Flex technology to ensure your feet are correctly placed
Cons
- No wide option available
Natalie Hammond is senior fashion news editor at Grazia. She previously worked at The Times - and has written for publications including The Telegraph, The Financial Times and gal-dem. She loves a ludicrously capacious bag (sorry, Tom!) and has never met a pair of clogs she wouldn’t wear.