2026-01-12

What to Wear With Chelsea Boots

Whether you’re dressing them up with pants and a blazer or dressing them down with a pair of ripped jeans, you have many options for what to wear with Chelsea boots.

With a number of styles and colors available for both men and women, Chelsea boot outfits can be worn for hikes, walks, dinners, or relaxing times with friends. In this guide, we’ll discuss some of the ways you can wear and style your boots.

How Do Men Wear Chelsea Boots?

Men wondering what to wear with Chelsea boots should keep in mind that leather boots often work well when paired with a formal suit or dress pants. They can also look great with a pair of jeans for more of a relaxed vibe. Adding a formal coat or a trench coat is ideal for either of these looks.

When it comes to choosing an outfit to go with men’s boots, jeans are a timeless option. Go for a slim-fit pair to keep it casual, or dress your boots up with a pair of black skinny jeans. If you’re going for more of a cool, collected look, try combining a simple crew-neck sweatshirt with super skinny jeans and your favorite boots.

How Do Women Wear Chelsea Boots?

Leather styles for women are more formal than suede, so combining our Women's Brimfield Mid Chelsea Boot with a dress and a light jacket for women is perfect for nailing the formal look. There are also more boots for women to choose from in general, so you’re sure to find a pair to go with any outfit.

When in doubt, jeans are really the best foundation for many Chelsea boots outfits. Whether you prefer to tuck a pair of skinny jeans into them or show them off with a pair of mom jeans, you can’t go wrong.

How to Keep Your Chelsea Boots Looking Fresh

When you’re choosing what to wear with 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.

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With their timeless style and streamlined design, Chelsea boots have become a closet staple for both men and women.

brown chelsea boot and black chelsea boot lying on the side

Why is it Called a Chelsea Boot?

Although this shoe style has a long history dating back to the reign of Queen Victoria, Chelsea boots only became known by this name in the 1950s and ‘60s. They were famously worn by many celebrities, 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 London borough of Chelsea. It’s thought that this is what gave the boots their name.

Chelsea Boot Outfits for Inspiration

With their timeless and versatile qualities, Chelsea boots have become a closet staple for many individuals. Depending on the style of boot you have, you can choose from a variety of options for what to wear with Chelsea boots, from combining them with a classic tailored coat to rocking them with a mini skirt.

Leather Chelsea Boots

Boots made with leather are the more traditional of the styles. Leather Chelsea boots can easily be dressed up for more formal occasions. Black usually works best with formal attire. However, brown leather boots like the Men's Redwood Falls Chelsea Boot also make a great option when you need to dress up without looking too formal.

Suede Chelsea Boots

Suede Chelsea boots are the more relaxed style, great for casual weekend outfits or informal events. Suede is usually manufactured and colored in traditional black and brown. Due to the nature of the material, it’s also possible to find other shades and colors.

Like leather boots, the color of the boot will have an impact on your style. Black suede is typically best for urban weekends in the city, whereas brown suede offers a more relaxed style. But you can always switch that up – it’s up to you!

brown chelsea boots on concrete with one lying on its side