How to wear chelsea boots

The Chelsea Boot is back in town for AW19. People are still divided and a common question we get asked hear at Base London HQ is, ‘How do I wear Chelsea Boots?’. SO here we have some great tips for you on how to style chelsea boots.

How to style Chelsea Boots 

Luckily for you, we’ve done our research here (a couple of hours on Pinterest counts as research yeah?) and found some common styling themes.

Please bear in mind these are merely opinions and guidelines. Unless David Beckham says any different, you can do what you want when it comes to styling your own Chelsea Boot. Speaking of which…

How to wear chelsea boots

The Tan or Brown suede Chelsea Boot

David Beckham typically wears Chelsea Boots and likes to pair them with a darker items to break up the look. Notice he hasn’t rolled the cuff of the leg on any of these looks. He’s happy to have a couple of trouser stacks, or have the break naturally about 2/3 up the heel.

There’s a welter of menswear writers and influencers that will be scratching their heads at this, as it does go against the grain a little. The idea of a boot is to show that it is a boot and not a shoe. But you’re David Beckham, you’re above the Chelsea Boot law.

How to wear chelsea boots

If you want to be taken seriously as a Chelsea Bootologist (not a word).. then it’s imperative that you find a wall to lean on. Some people make the mistake of walking all the way from their house to the shops without stopping and leaning up against a wall.

Others make the inexplicable mistake of leaning up against a wall whilst having both feet planted firmly on the ground. These really are the basics people.

How to wear Chelsea Boots the smart way for AW19

How to wear chelsea boots

If you’re wondering how to wear Chelsea Boots for SS19 the smart way, it is to go for a slimmer & angular silhouette.

Whilst the pointed Chelsea Boot is less versatile (the round toe Chelsea Boot is more interchangeable) you will have a very sleek, refined & assertive look for those meetings outside the office.

Does your Body Size matter? 

When it comes to styling, you’ll often find guys want to wear skinny or tight fitting denim. If you have a rugby type build, thick thighs, huge glutes.. you should be looking for more fabric on your jeans.

You can find a way round this, by wearing some cargo pants and having the zip undone at the cuff to accentuate the elastic band on the boot.

Alternatively, just have the break at the top where the cuff meets the boot. You can pull this look off without the skinny or tapered look.


In the mood for a new pair of Chelsea Boots for the season? Then shoot over to our Collection and browse our top Boot Styles.

Chelsea Boots