How to Wear Chelsea Boots | Definitive Style Guide

Chelsea boots – the most stylish boot in your collection?

Chelsea boots are ankle length boots with elastic side panels instead of zips or laces. Mens Chelsea boots have a long history of being smart yet cool, even a little edgy, being worn by many famous faces over the years. They are a must have in many well dressed men’s wardrobes as the mens boot of choice.

The elastic side panels or gussets mean that they can be put on and removed without needing laces. True Chelsea boots don’t have side zips. They normally have a loop at the back to make them easier to pull on.

Chelsea Boots History

The first Chelsea type boots were invented by Queen Victoria’s shoe maker J Sparkes-Hall in 1851. This had followed the recent invention of vulcanised rubber (elastic) by Charles Goodyear. They became quickly popular for walking and horse riding, and were worn my both men and women.

The second big wave of popularity began in England in the late 50s/early 60s with artists and musicians buying and wearing them around the King’s Road area in Chelsea, London. This is where most people believe they got their name.

Classic black chelsea - Beatles style

Photo: Classic black chelsea - British, sleek Beatles style.

The Beatles had some specially made for them with higher, cuban heels, to go with their stage suits, and these were quickly dubbed Beatle Boots. Many other bands and musicians wore them including the Rolling Stones, Kinks and Bob Dylan. John Steed in the Avengers famously wore black Chelsea boots with a pinstripe suit – brilliantly bringing together classic smartness with a sense of adventure.

Chelsea boots were popular with the fashion conscious Mods who often wore them with sharp Italian cut suits. In the US, Chelsea boots are sometimes called Dealer boots.

More recently they have returned to popularity again, often dressed down with jeans, photographed on celebrities such as David Beckham, Kanye West, Harry Stiles and David Gandy.

 Photo above: Black Suede Manhattan Style chelsea with a 40mm/1.5 inch heel.

Colours and Styles

Black Chelsea boots (above) have always been very popular and the classic choice. They go with many so many outfits. You can wear them for work and they look as good after hours and at the weekend. They can be worn with a suit, jacket, chinos or jeans, and this probably makes them the most very versatile. Also pretty versatile and a good choice, especially for your first Chelsea boot is dark brown leather, shown at the end of this post. Dark brown suede Chelsea boots can look great with many outfits too, especially if less formal.

Brogue punch toe design chelsea boot in aubergine/eggplant

Photo: Stirling brogue punch toe design chelsea boot in aubergine/eggplant

So black and dark brown leather are classic and the most versatile. Tan and light suede look great with jeans or chinos. But tan can work well with a mid blue suit if you want a bit of contrast. Some people go for a more individual look with other colours such as blue, shown below.

Most people prefer plain Chelsea boots but some also prefer some patterns or broguing, even a wingtip style.


Tan Suede Chelsea Boots

 Photo above: Tan Suede Manhattan Style chelsea with a 40mm/1.5 inch heel

Blue chelsea boots

Light brown/tan chelsea boots with blue jeans

Chelsea Boots Fit

Because there are no laces, which can offer a little adjustment, a good fit is important, especially around the instep and heel, so the Chelsea boots fits snuggly and doesn’t slip. Good construction and materials help here.

What about trouser length? Fashions and opinions vary but we think mens Chelsea boots look best if the trousers fall no more than an inch or so below the top of the boot. This avoids the crumpled look that spoils the sleek lines of the boot. This depends on your own style but it’s worth getting this right.

Thomas Bird Italian Made Chelsea Boots

Thomas Bird currently offers seven different mens Chelsea boots, all made in Italy using high grade full grain calf leather. They are dyed and burnished by hand to give a beautiful depth of colour. They all have a full leather lining and a loop at the back. Colours include black, dark brown, dark brown suede, light brown/tan and blue. We offer two soles, one classic with a leather sole and rubber insert for longer life, and one with a heavier duty commando type rubber sole. All are plain, with no broguing to maintain that cool, sleek look. We’ve shaped our Italian made Chelsea boots so they are sleek and European in look, but fit snuggly and hold the heel securely.

Grey Suede Chelsea Boots

Black chelsea boots with blue jeans

Photo: Eastwood black chelsea boots with commando style rubber sole

In Conclusion – are Chelsea Boots right for you?

If you want to look smart, but want a little edge and attitude, if you want something different to your usual oxfords and brogues, then give the classic Chelsea boot a try. Think about colours and how and when you will be wearing them. Then dive in. We think you will look and feel great!

Discover our full range of Chelsea Boots here and tell us what you think.

Thomas Bird London