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12 best women’s boots for stomping into winter in style

The chill in the air means it’s time for our summer outfits, sandals and trainers to be pushed to the back of our wardrobes, leaving room for a winter refresh.

And with autumn’s arrival, boots have once again returned to our sartorial arsenal. Whether ankle grazing or knee high, chunky or refined, with a flat or a high heel, the right pair can effortlessly complete your look and be trusty pals for years to come.

While calf-high models, Bottega-inspired track sole designs and cowboy boots are back for another year, there are some newer trends you can expect to see everywhere this winter, including square-toe fits, knee-high silhouettes and equestrian-inspired riding boots. And after more than a year of various lockdowns and favouring comfort on our feet – namely slippers – it’s no surprise that practical, reliable stompers and wellie-esque boots are also reigning supreme this season.

How we tested

When appraising how versatile each shoe was, we mixed and matched them with different outfits to divide them into everyday and going-out pairs. We also considered the design, aesthetic, fit and feel of the boots while wearing them each for short and sustained periods in order to test their durability, comfort and support. Particularly with uncomfortable pairs, we wore them again to see if they improved over time.

We took inspiration from fashion fads as well as enduring designs; so put your best foot forward and tread into the colder season in style.

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The best women’s boots for 2021 are:

  • Best overall – Karen Millen knee high leather flat boot: £119.20, 
  • Best sustainable boots – Lemon Jelly city 04 boots: £129.90,
  • Best lace-up boots – Hobbs Issy leather lace up ankle boots: £199,
  • Best statement boots – Monki Polly knee high boots: £55, 
  • Best chunky chelsea boots – H&M chunky leather boots: £79.99,
  • Best riding boots – Mango leather boots with tall leg: £139.99, 
  • Best platform boots – Asos Design Rochelle leather platform boots, camel: £85,
  • Best everyday boots – All Saints Billie leather boots: £249,
  • Best classic boots – Dr Martens black 1460 bex boots: £169,
  • Best western-style boots – Maje ankle boots: £379,
  • Best sock boots – Reformation Louie sock bootie: £300,
  • Best cowboy boots – Mtng cowboy boots: £104.99,

Karen Millen knee high leather flat boot

Best: Overall

Rating: 9/10

Tap (and tread) into both the chunky and knee-high boots trend with this pair of Karen Millen stompers. Track soles were everywhere last year, and this autumn/winter they’ve been given a knee-high upgrade. Designed for winter wear, the raised soles are durable and tough-looking, contrasting the Italian leather and flattering knee-high fit. As with most good-quality boots, it takes a couple of outings to wear them in, but the pay-off is worth it; whether worn with opaque tights and a mini skirt or a knit dress, they’re an instant winter staple. These boots are sold out at the moment but we hope they’ll be back soon.

Lemon Jelly vegan mid calf brown boots

Best: Sustainable boots

Rating: 9/10

What is first noticeable about this gorgeous pair of boots is the scent – as soon as you open the box you are hit with the zesty smell of lemons; the brand’s signature touch. Secondly, the weight of the boots blew us away – they felt like feathers on the feet. Our tester, bravely, decided to test them out at a gig and, despite chunky boots being notorious for blistered heels, came home feeling sprightly.

We didn’t think it was possible, but Lemon Jelly has made wellington boots look cool. The rich autumnal shade of brown elevates the look, and the chunky sole is very on-trend. The fact that they are sustainable, vegan and waterproof is just the cherry on top.

Hobbs Issy leather lace up ankle boots

Best: Lace-up boots

Rating: 8/10

These elegant ankle boots from Hobbs are crafted from premium leather and boast a 5cm stacked block heel. If, like us, you’re an unseasoned heel wearer, they prove a comfortable compromise, and the leather sole has rubber foreparts that help with grip. The lace-up design and square toe are bang on trend, and there’s a side-zip fastening for ease. Sartorially versatile, team these with everything from a midi skirt to kick-flare jeans or a jumpsuit. You can sign up to receive an email when these are back in stock.

Monki Polly knee high boots

Best: Statement boots

Rating: 9/10

Award your look a 1960s flair with these Monki boots and their effortlessly cool black and white checkerboard design. In vogue with a knee-high fit, square toe and mid-height chunky heel, the retro print gives the boots some edge. Best worn as the focal point of your getup, team with a neutral or block colour outfit or dress. Coming in at £55, they’re markedly cheaper than most good-quality boots on the market, and we were also pleased to discover that they are vegan. While these boots are out of stock right now, you can choose a different colour or sign up to receive a notification when this pair is back.

H&M chunky leather boots

Best: Chunky chelsea boots

Rating: 7/10

The chunky Bottega-esque chelsea boot isn’t going away soon, and these H&M examples are a nice take. Coming in a versatile light beige colourway, they give you an added 5.5cm of height without the discomfort of heels, while the low calf height and loops on the shaft add detail. A great way to refresh your wardrobe for autumn, pair them with light blue jeans or with a midi dress and trench.

Mango leather boots with tall leg

Best: Riding boots

Rating: 8/10

Since Princess Di took riding boots out of equestrian circles and into the fashion crowd, high-rise shoes have consistently come in and out of vogue. Kate Middleton and the Olson twins are fans, and the style has been spotted all over runways, from Celine to Coach. This pair of Mango black boots are a perfect example and boast a rounded toe, flat heel and wide fit around the calves. One of the easiest boots to style, opt for a preppy look by wearing over an equally timeless pair of skinny jeans, or pair with a mini or midi dress to elongate your legs. They’re a sure investment that will see you through this winter and beyond.

Asos Design Rochelle leather platform boots, camel

Best: Platform boots

Rating: 7/10

If Monki’s Sixties-style boots didn’t satisfy your retro predilections, these Seventies-inspired platforms are sure to get you humming Abba. While we can’t praise them as a great everyday pair, they instantly complete an outfit on a night out. The camel colourway is a versatile shade that goes with most things in your wardrobe, while the ankle-grazing fit means they work well with kick flares if you’re opting for a truly 1970s-style look. At 8cm high and with a square toe, they take some wearing in, but if you’re willing to accept some discomfort, it’s certainly worth it.

All Saints Billie leather boots

Best: Everyday boots

Rating: 9/10

If you’re after the perfect on-trend everyday boots, then this is the pair for you. Part chelsea boot, part biker boot, these leather shoes have a flattering calf length and subtly give you some extra height with a chunky sole.  Surprisingly comfortable during their first outing (a rarity in this round-up) as well as sturdy and structured, the costly price tag is owed to the quality – they’re a sure investment for year-on-year wear. This pair is currently out of stock.

Dr Martens black 1460 bex boots

Best: Classic boots

Rating: 9/10

An instantly recognisable boot for very good reason, Dr Martens has been an enduring name in footwear since its founding in 1947. This pair of 1460 bex boots are in the brand’s emblematic style, with an ankle-grazing fit, black leather upper, eight-eyelet lace-up design and yellow stitching to finish. The slightly chunkier sole of the bex model gives them a contemporary feel that still retains the durability, comfort and looks of the classic pairs. Dr Martens work all year round – worn with jeans, a skirt and midi or mini dress – but come into their own during winter. You really can’t go wrong.

Maje ankle boots

Best: Western-style boots

Rating: 8/10

A trend that shows no sign of waning is cowboy-inspired boots. This pair of ankle-grazing ones from Maje give a subtle nod to the style but are an investment that will last beyond the fashion fad. The design’s tapered end and metal tip, cuban heel, pull tab and elastic panel overlayed with stitched leather bands work to create a boot that’s intricately detailed and can add interest to the simplest of outfits.

Reformation Louie sock bootie

Best: Sock boots

Rating: 9/10

Sleek and versatile, sock boots are a must-have in any shoe collection. The fitted silhouette of this pair is flattering, while the tight material helps to create a seamless look on the leg. Whether poking out of long-length jeans, worn with kick flares or with a louder outfit in the evening, they can make a look feel more glam and put-together. This sage green pair with a square toe and stacked heel fit like a glove and are supremely comfortable.

Mtng cowboy boots

Best: Cowboy boots

Rating: 8/10

An enduring trend since 2020, designers from Saint Laurent to Isabel Marant have been making the case for cowboy boots. This authentic-looking pair has intricate embroidering and a V-shaped opening. Made from leather, they’re easy to pull on and boast a pointed toe and block heel that are comfortable underfoot. Coming in black, they’ll easily slot into your wardrobe and can be paired with everything from a mini skirt and opaque tights in the winter to a floaty mini dress when summer comes back around. In comparison to some cowboy boots on the market, they’re reasonably priced too.

IndyBest product reviews are unbiased, independent advice you can trust. On some occasions, we earn revenue if you click the links and buy the products, but we never allow this to bias our coverage. The reviews are compiled through a mix of expert opinion and real-world testing.

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