The must-have boots for winter, from the lowest to the highest heel

Biker, slouchy, wedge... Which one are you going to take your first step with this season?

29 September 2025

Now that the temperatures are (finally) starting to drop, there is one wardrobe basic that will be taking centre stage in all of our looks. We are talking, of course, about boots for winter. Whether you opt for a pair of classic Chelseas, or opt for an edgier, chunkier option, your boots of choice will undoubtedly transform each and every look you choose to step out in.

The MustHave Boots for Winter From the Lowest to the Highest Heel

Here, we present you with all of the styles that are set to dominate the streets this season, ordered from lowest to highest heel. From the most trendy slouchy boot through the classic Chelsea, these are the boots for winter that will be making the biggest footprints.

Classic Chelsea boots
£229
Flannels
Nothing really beats the classic Chelsea silhoutte. One of the most versatile boot styles out there, the Chelsea boot is perfect for a wintery walk or an evening out. Plus, with this itty bitty heel, you'll be able to stomp all over town without feeling a thing.
Biker boots
~~£195~~ £119 (39% off)
& Other Stories
If you're looking for something with a little more edge, you can't go wrong with a bold biker boot. The buckles on this pair will give your winter walk a bit of flare.
Round toe boots
£169
& Other Stories
Another classic silhouette is the round toe boots. With a moderate heel, this pair will take you seamlessly from autumn to winter – and will stay in style for years to come.
Wedge boots
£169
Boden
For a Y2K moment, try the somewhat controversial wedge boot. Admittedly, the wedge shape comes in and out of style — but right now, the Y2K revival means that this unusual heel is firmly in the ‘in’ category.

Cowboy boots
£169
Massimo Dutti
Another timeless style is the cowboy boot. This shape will add a boho edge to any look, while the chunky heel will add the perfect amount of height for an eveningwear look.
Wide heel boots
£605
Net-a-porter
If you want to experiment with a serious, towering heel, but still want to feel, you know, supported, a wide heel is the solution you've been looking for.
Slouchy boots
~~£65.99~~ £30.50 (54% off)
ASOS
Effortlessly cool and more interesting than some of the other classic styles out there is the slouchy boot. With the delicate heel on this pair, you'll always have the perfect going out out boot.
Snakeskin boots
~~£170~~ £52 (69% off)
Flannels
If you want to make a real statement, look no further than this high drama, high heel snakeskin boot. Pair them with skinny jeans or a mini skirt to really showcase the shoes.

Sock boots
£59
John Lewis
There's something decidedly chic about the ankle-hugging sock boot. This stylish pair will have you towering over the city with its XXL heel.
Stiletto boots
~~£690~~ £489 (29% off)
Flannels
Finally, we have the classic stiletto. The ultra high, no-nonsense heel usually reserved for serious events can also be a street style staple.