The Best Boots for Women this Autumn and Winter
February 04, 2025
With cooler days just around the corner, you'll want to make sure that your feet are ready to step into rain and snow in style. The best boots for the autumn and winter seasons should be cosy and comfortable, to keep your feet snug and supported, weatherproof to tackle the rain and mud, but also ready to make a statement.
With that in mind, we've put together the ultimate guide to buying the best boots for women that are affordable, high-quality, and trendy at the same time..
What's on this page:
What boots are in style this autumn and winter?
Chunky and high boots are definitely 'in' this season, with a focus on bright colours, patterns, and bigger details. Besides face-value style, functionality is also a fashion priority, so you'll find plenty of fashionable versatile boots to browse, like ankle and Chelsea boots.
From street style to knitwear and evening outfits, we've prepared a best boots guide that ensures you have the perfect pair to suit all occasions - while still keeping up with the latest trends.
Some of the best styles of women's boots this autumn/winter include:
- Biker boots - add an edgy look to your outfit. This style is the perfect pairing for a classic leather jacket or even as a statement with a long dress and oversized cardigan.
- Ankle boots - wear them with almost anything. These boots are a wardrobe must-have, going well with almost any style of jeans, coupled with a basic tee or formal top.
- Calf and over-the-knee boots - great for keeping your legs warm while adding a little bit of class. These statement shoes go well with dresses, jeans, miniskirts - you name it.
- Chelsea boots - practical and timeless. Chelsea's feature their famous elastic side panels, to easily slip them on and off, while adding that statement look.
- Chunky boots - durable and comfortable, perfect for everyday wear. Chunky boots come in all shapes and sizes (but mainly chunky) and add a bit of edge to any wardrobe.
Check out our picks for the best autumn/winter boots below.
The best biker boots for women to add statement style
Originating in the motorcycling era, which has its roots all the way back in the late-nineteenth century, biker boots are great outdoor shoes that feature utility details, such as buckles and zips. They offer an edgy, contemporary look, especially when paired with jeans and a leather jacket, or a vintage dress or overalls.
Lilley Miley Womens Black Knitted Collar Boot
For a military-style boot with a twist, the Lilley black lace up boots offer stylish security. Sleek and sturdy, with a round toe front and laces for extra security. The black knitted collar adds an extra bit of cosy detail.
Top Tip: Match these boots with a knitted cardigan and a pair of skinny jeans for a casual seasonal look.
Lilley Monica Womens Black Lace Up Ankle Boot
These black chunky ankle boots by Lilley include fine stitching, lace up fastening, and thick soles for extra comfort. These boots boast a classic combat shape, so are a must-have wardrobe addition for the colder seasons.
Top Tip: Wear these staple shoes with jeans and a jumper on a casual day, or tights and a long skirt when the rain is letting up a bit.
The best ankle boots to compliment your winter wardrobe
Since 1804, when they were first introduced, ankle boots have been a fashion staple. With so many different styles and materials available, come so many ways to wear ankle boots. From workdays to casual walks and formal events, ankle boots are so versatile to suit most occasions. We have a wide selection of women's ankle boots to choose from.
Lilley Miranda Womens Taupe Zip Up Boot
These classic taupe ankle boots will never go out of style. Featuring a stylish ruched upper, a zip for an easy fit, and a buckle design, this shoe is ready for both friend dates and country walks.
Top Tip: Inspired by countryside style, these boots are begging to be paired with vintage knitwear, floral skirt, and cosy socks.
Lilley Maggie Womens Black Lace Up Boot
The lace up black boots are a great purchase for everyday wear and for those colourful autumnal walks. The faux fur trim and warm lining provides additional support and warmth, while the extra-thick outsoles help with grip and durability.
Top Tip: These boots are perfect for the outdoors, whether going on a walk with family or stepping out to shop. Pair them with jeans or cargo pants, depending on your destination.
The best over-the-knee and calf boots to add elegance
Over-the-knee and calf boots are not just made to keep your legs warm - they're made to make a statement. Originally worn by equestrians, calf and knee-high boots are very popular in the world of celebrities. Kate Moss, the Kardashians, and J-Lo are among the big names that have been seen wearing these iconic shoes. They complement dresses and casual outfits, but also office and formal wear.
If you struggle to keep knee-high boots up, we've put together some tips to help you in this handy guide.
Lilley Mindy Womens Black Riding Boot
These black riding boots from Lilley are the perfect pair of autumn/winter boots. Stylish, featuring buckle straps, elasticated panels for easy fitting and a block heel to add some height.
Top Tip: For a look fit for the office, style them with a calf-length sweater dress and an oversized blazer.
Lilley Milan Womens Black High Leg Heeled Boot
For a glam, evening look, pick a pair of these black high leg heeled boots designed by Lilley and be ready to shine. They feature a side zip for easy fitting and a stylish block heel for added height.
Top Tip: Team with a leather skirt and a lacy blouse for a special date night, or tone-down with a pair of jeans and a blazer for a day on the Highstreet.
The best chunky boots that'll get you through the winter in style
Chunky styles are popular right now, with celebrities like Miley Cyrus, Olivia Rodrigo, and Gigi Hadid regularly wearing them to make an impact. They're sturdy, comfortable statement shoes that offer the right support for everyday use. Explore our collection of chunky boots and upgrade your autumn/winter wardrobe.
Lilley Mildrid Womens Black Chunky Ankle Boot
These stylish black chunky boots from Lilley feature elasticated panels and a pull tab to easily get them on and off. Their chunky outsoles add height and offer a stable grip, while maintaining that must-have chunky boot shape.
Top Tip: For a grungy twist, add them to a colourful or patterned mini skirt or a dress, complete with an oversized blazer.
Lilley Mavis Womens Black Chunky Chelsea Boot
From Lilley, the Mavis chunky boots offer an easy pull on design and a lightweight feel and comfort. These amazing boots offer an edgy style with their chunky sole - perfect for adding that little something extra to any outfit.
Top Tip: For an edgy outfit, tuck some skinny jeans into your boots, finish with a blazer and a belt.
The best Chelsea boots that'll never go out of fashion
Dating back to the 1850s, Chelsea boots are both timeless and chic. The elastic side panels, snug fit around the ankle, and lightweight body make them the ideal shoes for autumn. They are a slightly more traditional style of boots that fit semi-formal wear; however some styles are suitable for casual wear. Our Chelsea boots come in a variety of colours and styles, all keeping that must-have classic look.
Lilley Molly Womens Black Chelsea Pull On Boot
These classic black Chelsea boots are a great finishing touch to any outfit. The pull-on loop makes them even easier to slip on and the round toe helps to create that classic Chelsea silhouette. The matte finish and sturdy grip sole make this pair a staple, whatever your style.
Top Tip: For a relaxed look, wear them with tights and a skater skirt, or throw them on with a pair of skinny jeans and a neutral tee for those more casual days.
Lilley Morag Womens Black Chelsea Boot
Add some height and style with a pair of chunky Chelsea boots. The thick platform sole provides a stable grip and the all-black upper provides extra stylish detail. These boots easily slip on and off and their snug elasticated inserts mean you'll be ready to take on the colder seasons.
Top Tip: These classic-shaped boots work well with ripped jeans and cropped, leather jackets.
Check out the shoezone blog for more style tips and footwear suggestions for every occasion.