When it comes to winter boots, nothing is as classic as Chelsea boots. They can be traced back to Victorian times, when Queen Victoria’s shoemaker Joseph Sparkes is said to have invented the style and claimed that the Queen wore them every day. At the time, this was quite the endorsement for this practical walking shoe style. In the ’60s, they were a regular sighting on the King’s Road in Chelsea, London, where they became established as a fashion-forward choice. Fast forward to today, and they remain the cornerstone of many stylish wardrobes, with small tweaks helping drive forward the design and ensuring they remain relevant every season.
Chelsea boots typically have a close-fitting body, which hits just at the ankle, with elastic panels at either side to help provide support and ensure they can be easily taken on and off. A classic Chelsea will also feature a fabric tab at the back (another design detail to help pull on the boots with ease) and low heels. That said, in recent years, the Chelsea boot style has undergone several transformations, moving away from its royal associations and having a more punk-inspired aesthetic. Several seasons ago, the likes of The Row, Bottega Veneta, Prada, and Ganni sparked a trend for chunky Chelseas, with thick lug soles, a higher shaft, and a glossy finish. Thanks to the weighty tractor treads, this style of boots adds toughness and plenty of attitude to any outfit. Although these remain a popular option for those who have a high daily step count, this year’s dominant Chelsea boots have a sleeker look and feel.
Khaite's Marfa Chelsea boots are a key trending style.
Brands such as Toteme, Khaite, and Aeyde all create beautiful "city" Chelsea boots, which all have a sleek design with a more sculptural, pointed toe and low Cuban heel. Toteme's City boots have a tab at the front and back, which is a thoughtful yet subtle modern twist on the classic design. Chocolate brown and suede Chelsea boots are also proving popular this winter, in line with the wider color and texture trends we are seeing across the board.
Keep scrolling to check out the best Chelsea boots our editors love for this winter and beyond, with a mix of designs from classic to sleek.
A pair of square-toe Chelsea Boots by The Row.
Shop Our Edit of the Best Chelsea Boots
These will add a London edge to any outfit, and the contrast stitching makes them identifiable as Dr. Martens.
With cushioned footbeds and lug soles, these will be practical walking boots. Plus the brown leather will only look better as it ages.
We love how the black elastic on the ankle looks with this "old rum" leather.
The toffee suede makes these look very current.
Ganni has been largely responsible for the chunky Chelsea trend and it is still a core product for the Scandi brand.
This Berlin-based brand created the most beautiful boots, and its ankle boots are a hero design.
Trust Manolo Blahnik to craft the perfect Chelsea boots.
Proenza Schouler's Chelsea boots are always loved by fashion editors.
These have a more Western feel thanks to the higher Cuban heels, pointed toes, and suede finish.
Trust Toteme to craft the chicest Chelsea boots that are made from beautiful Italian calfskin.
The square toes and slanted heels make these look more design-led.
Simple and perfect.
A more subtle take on chunky Chelsea boots that will be a versatile everyday option.
These have reached cult status and are particularly beautiful realized in this deep coffee shade.
The Campo is Loewe's take on Chelsea boots.
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