How to nail Chelsea boots this autumn

How to nail Chelsea boots this autumn - Leonard Silver

Hailing from the Victorian era, the Chelsea boot has been a mainstay of the British gent’s wardrobe for more than over a hundred years. And whilst it might have varied slightly in production methods and nuances, ultimately it remains quintessential footwear renowned for its smart appearance, sturdy nature and versatility.

With autumn upon us, and winter fast approaching, the famous Chelsea boot will be the choice of many as the seasons begin to turn. But how to wear them and what to wear them with can be a difficult choice to make.

So here’s our guide to how to wear a Chelsea boot like a true, sophisticated chap.

1. Know the history
Whilst the heritage of the boot is founded in hiking and horse riding, following their adoption by a group of artists, musicians and designers who were closely associated with the King’s Road area in Chelsea they earned a change in name (they were previously known as Dealer or Paddock boots). Once they had garnered this reputation they quickly began to be widely adopted by rock stars and fashionistas from the Beatles to Pete Doherty.

This should be what informs your look when putting together an outfit. Think about trench coats, fitted jeans and shirts. You could even throw in a trilby hat.

2. Find the right fit


As you will probably be aware, Chelsea boots come with an elasticated section of the boot around the ankle to allow the foot to slide in. This indicates the boots should be fitted and not gaping or sagging around the ankle. However, they shouldn’t rub or push your toes together, ultimately they need to be a comfortable fit. If it’s your first time wearing Chelsea boots then it’s worth going to a high-street stockiest (rather than ordering online) and trying a couple of sizes before making a final decision.

3. You get what you pay for

Whilst having a budget is fine – we all have a finite amount of money – it’s worth investing in a proper pair of boots that will last you a number of years, instead of plumping for a cheaper pair that are likely to fall apart fairly quickly. This doesn’t necessarily mean you have to stray from the high street these Lacuzzo tan boots with statement red elastic will go great with any outfit.

4. Pairing them with your trousers

In general, men’s boots have a bulkier finish to them, which causes trousers to bunch at the ankle. However, the Chelsea boot has a much narrower design, so the trouser leg must hang over the top of the boot. There’s really no limit to the type of trouser you can wear – just don’t wear them with shorts! It’s this versatility that means they can even be worn with a suit. They’re not the style of shoe that immediately spring to mind when dressing for a formal occasion but the fact they fit seamlessly under a trouser leg as well as their smart finish make them a fashionable option.


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