How To Wear Chelsea Boots for All Occasions

Also known as Jodhpurs or Paddock boots, Chelsea boots have many similarities – however contain slight differences, such as not having a strap like Jodhpurs the and instead having the elasticated side that everyone now associates with the classic Chelsea boot look.

This boot is unfussy, clean-looking and a staple to any outfit and a very popular choice amongst the royals too. Having Victorian roots, these boots were first recorded to be worn by Queen Victoria herself on regular occasions. 

M&S Suede Chelsea Boots
Source: M&S

They have many benefits. They are durable, comfortable and (with the correct accompaniments) are highly fashionable.  

But, what are the correct accompaniments you ask? 

The following is a guiding to choosing and styling the ‘Chelsea boot’ to suit any style or occasion. 

Ageless Fashion 

With their timeless charm and adaptable demeanour, you can dress them up, dress them down and then back again. They never get old. But don’t just take it from us take it from the fashion icons themselves. 

The Chelsea boot were a popular choice amongst the most famous celebrities including the Beatles. In fact, for a short while, the Chelsea boot was renamed the ‘Beatle boot’, for a short while’ after being worn by the band in 1962. 

The Beatles wearing Chelsea Boots‘The Rolling Stones’ were also captured wearing the famous ‘Chelsea boot’ as well as being the footwear for the storm troopers in the star wars trilogy.  

How to Choose a Pair of Chelsea Boots?

The following are a few details you should consider before choosing you perfect pair of Chelsea boots:

  • Originally the Chelsea boot had a leather sole. For a more traditional look and feel, opt for the leather sole, although some brands offer the Chelsea boot in a variety of sole types. The leather is always the one you should sway towards for that traditional look. 
  • Some ‘Chelsea boots’ are sold with a zipper up the side or some additional features. However, these are not a traditional Chelsea boots. A traditional boot are elasticated on both sides and are ‘pull-on’. 
Ted Baker Leather Brown Chelsea Boots
Source: Ted Baker
  • Don’t rely on standard shoe sizing. These boots rely on the elastic on the side panels of the boots, rather than the sole. Therefore it is essential that you try the shoe on to make sure it fits perfectly. 
  • Due to the elastic being an essential part of the boot, it is important you check the quality of that elastic. This will determine not only the comfort, but also the longevity of the boot. 

How to style the Chelsea Boot

Do to their clean and classic look, Chelsea boots are very versatile and can be fashionably styled with jeans and a suit alike. For a more traditional look choose a thin sole to tie in with the sleek look of the Chelsea boot, although thicker soles are more durable, a think sole is a classic look. 

The boots are available in a variety of different colours and fabrics. Leather fabric is the classic boot although suede is a good alternative. 

In black, the boot looks great styled with denim or a suit, although maybe slightly too casual for a tuxedo. With the black boot try and style with darker colours.

M&S Black Leather Chelsea Boots
Source: M&S

Black compliments black and so the black Chelsea boot would look great with a black suit or if you’re wanting to wear them with jeans, darker jeans and a navy blazer is a classic look. 

For the lighter boots (usually brown or tan) try styling these with navy or grey suit. Top tip, if you’re wearing a lighter suit, such as grey or navy and then a lighter Chelsea boot, such as brown or tan, then try and tie with accessories. This could be a belt that matches the boots.  

Lighter Chelsea boots would also suit a tweed suit or for a more casual look try pairing with denim (preferably straight cut) and a polo shirt. 

When pairing with any full length trouser, always leave the trouser hanging over the Chelsea boot, never tuck them in. Although, this may be tempting it is much more complimentary to both the boot and your outfit to leave the trouser untucked. 

River Island Brown Chelsea Boots
Source: River Island

Top tip: if you usually wear longer fitting trousers may we suggest that you take those up a few centimetres. This way you will have full boot pay off. Remember you’ve paid money for these boots, don’t hide them way under your trousers, show them off loud and proud. 

To shine or not to shine? That’s the question. We recommend that a shiny patent shoe is a much more desirable look for a smart suit and occasion wear. Whereas the matte or suede look compliments a more casual and ‘laid-back’ look whilst still looking smart. 

The Last Word

Although the Chelsea boot is a very versatile and easy-to-wear shoe choice, there are a few tips and tricks that you should know before purchasing and styling the boot. To conclude, make sure the shoe is fit perfectly, rather than just going off standard sizing and also make sure your jeans are over not tucked into the boot. Follow these key steps and you’re ready to go and purchase your staple ‘Chelsea boot’. 


Paul Inman

Paul Inman is the founder of The Bald Gent. As the main contributor to TBG, Paul has years of knowledge, experience and stories to share with our users. His insights, advice and blogs form the backbone to everything we do and what makes being a true gent so important to the ethos of TBG.

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