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What to wear with Chelsea boots


What to wear with chelsea boots


Chelsea boots have become a wardrobe staple for many of us and their versatility knows no boundaries; whether you’re dressing them up for any occasion with smart trousers and a blazer or dressing them down with a pair of ripped jeans.

With a number of styles and colours available for both men and women, Chelsea boots are the perfect companion for any outfit and occasion. In this guide, we’ll discuss some of the ways you can wear your Chelsea boots.

Why is it called a Chelsea boot?

Although this style of boot has a long history dating back to the reign of Queen Victoria, Chelsea boots only became known as such in the 1950s and ‘60s when they were famously worn by everyone from the Rolling Stones to the Beatles.

Throughout the swinging sixties, these stylish ankle boots had a strong association with the King’s Road in the borough of Chelsea and it’s thought that this association is what gave the boots their name.

What can I wear with Chelsea boots?

Depending on the style of Chelsea boot you have chosen, there are a few different outfits that look great when partnered with a pair of these ankle boots; from combining them with a classic tailored coat to dressing them down with a pair of ripped jeans.

Leather Chelsea boots

Chelsea boots made with leather are the more traditional of the styles and tend to be the smarter of the two options. Leather Chelsea boots can easily be dressed up for more formal occasions, of which black typically works best. However brown leather Chelsea boots, such as the Timberland Stormbuck Chelsea boot for men, are also a smart choice for when a slightly less formal and a more casual look is required.


Suede Chelsea boots

Suede Chelsea boots are the more relaxed style of the two materials often used to make Chelsea boots and are a great addition to casual weekend outfits or smart-casual occasions. Suede is usually manufactured and coloured in traditional black and brown, however, due to the nature of the material, it’s also possible to find additional shades and colourways.

Like leather Chelsea boots, the colour of the boot will have an impact on your style. Black suede is typically best suited to urban weekends in the city, whereas brown suede offers a more traditional, countryside style.

How do men wear Chelsea boots?

For men, leather Chelsea boots, like our Oakrock Chelsea boots, work well when paired with a formal suit or dress trousers but can also look great with a pair of jeans for more of a relaxed look. The addition of a formal coat or trench coat is ideal for either of these looks.


When it comes to choosing an outfit to go with suede Chelsea boots, jeans are a great option; opt for a slim fit pair to keep it casual or dress your boots up with a pair of black skinnies. If you’re going for more of a cool, calm and collected look, try combining a simple roll-neck jumper with super skinny jeans and your favourite Chelsea boots.

How do women wear Chelsea boots?

Leather styles for women are more formal than suede, so combining ankle boots with a dress and trench coat is perfect for nailing the smart-casual look. There are also often more colours for women to choose from so you’re sure to find a pair to go with any outfit.

Jeans are really the best companion for a pair of suede Chelsea boots, whether you prefer to tuck a pair of skinnies into them or show them off with a pair of cropped mom jeans.

Whatever you choose to wear with your Chelsea boots, make sure you keep them protected in all weather conditions with our Waximum Waxed Leather Protector or our Balm Proofer Water & Stain Repellent.

Still looking for inspiration? Look at how to style men's chelsea boots.