Best Chelsea Boots for Men: 8 Classic Pairs Style Experts Recommend

The Chelsea boot is one of those items of footwear that’s never truly gone out of style since its inception, way back in the Victorian era. Sure, they’ve been more popular at some times than others—they were a core part of the look of London’s Swinging 60s scene—but you could wear them in pretty much any decade and feel good about it. We’ve rounded up our current favorites, so put down those tennis shoes and check out the best Chelsea boots for men.

Our top picks for the best Chelsea boots for men

What to consider when buying Chelsea boots for men

There are various factors to keep in mind when purchasing Chelsea boots, and Loiseau says to pay special attention to the following:

Material

High-quality materials, Loiseau explains, are vital in order to guarantee long-term durability and comfort. “Chelsea boots that are made of premium leather exude sophistication and age beautifully over time,” he says. “I encourage ethically sourced leather or vegan alternatives, which reflect values of sustainability.”

Price

Boots can be expensive, but if it’s a pair you’re going to wear for years, it may well be worth the initial investment. “Research brands offering exceptional craftsmanship without breaking your budget,” Loiseau suggests. “Investing in well-made pairs will save you money in the long run because they will last you longer!”

Function

Obviously, you’re going to want to think about where you’ll be wearing your boots—are you looking for a pair for formal occasions, casual nights out, or both? Loiseau points out that the boot’s sole, grip, and overall construction all need to be equally considered when making your selection.

How we selected the best Chelsea boots for men

We chose our entries here by following the advice of our trusted experts, who have years of experience in the world of shoes and men’s clothing brands more generally. We also ensured that each of our entries was highly rated by customers, only including those with positive reviews, touting comfort, fit, look, and durability.

What is the best color for Chelsea boots?

“When it comes to fashion choice, color is one of the most subjective elements,” says LaGrone. “For shoes, men tend to veer on the safe side, sticking to dark neutrals that can match everyday attire. Most people have the least amount of shoes compared to other clothing pieces in their wardrobes, so it makes sense they want them to be as cross-functional as possible. However, given the leather construction of Chelsea boots, there are many colors available, and the elastic banding on the ankle provides the option to add an accent color. Glossy blacks and browns, suede medium browns, and deep burgundies are all very popular and classic colors for a Chelsea style.”

What are the different types of Chelsea boots?

“The Chelsea boot has a long history, dating back to the 18th century, and its style has changed a lot since,” says LaGrone. “The basic premise of the Chelsea boot is that it’s a boot that can be easily slipped on without the need for laces or buckles. For this reason, it also quickly gained popularity.”

“All Chelsea boots are ankle boots, characterized by the elastic band and ankle pull tabs,” continues LaGrone. “As established, they can vary in material, with the most common men's styles featuring leather. But other types would be rubber, exotic skins, patina finish, shell cordovan, suede, and various fabric materials. Other characteristics may include having heeled, platform or chunky-sole Chelsea boots, however, these are most commonly seen in women's fashion. For men's fashion, most of the variation will be in the toe design, whether it is pointed, rounded or squared, and whether or not it features a wingtip design. Any styles that begin to veer away from the elastic band and ankle tab styles would be classified as just ankle boots, and not a type of Chelsea boot.”

Below, Loiseau breaks down a few common styles of Chelsea boots, and how to recognize them:

Classic Chelsea Boots

“These boots boast an elegant silhouette, with elastic side panels for ease of on/off wear as well as a rear pull tab, providing quick on/off. Known for their timeless appeal.”

Brogue Chelsea Boots

“These boots feature elaborate brogue details, like perforations or wingtips, that add sophistication and character to their classic Chelsea design.”

Suede Chelsea Boots

“Crafted of soft suede rather than leather, these Chelsea boots provide a casual and relaxed aesthetic, perfect for creating stylish yet laid-back looks.”

Chelsea Boots with Rubber Soles

“While traditional Chelsea boots feature leather soles, rubber-soled ones provide enhanced traction and durability, making them suitable for various weather conditions.”

Frequently asked questions (FAQs)

What are the best brands for Chelsea boots for men?

Loiseau has a few recommendations, as follows:

Grenson

“This iconic British brand is known for their expert craftsmanship and commitment to ethically sourcing leather products, offering classic and modern Chelsea boot options.”

R.M. Williams

“R.M. Williams of Australia is well known for making boots crafted with superior materials that combine sustainability with ethical production methods, to provide long lasting shoes and boots. They prioritize sustainable practices for production to guarantee product durability for years.”

Common Projects

“This luxury minimalist brand prides themselves on using clean lines and premium materials in their Chelsea boot designs, meticulously hand-crafted, often featuring subtle yet distinctive gold serial number branding.”

Thursday Boot Company

“Offering fashionable Chelsea boots made of ethically-sourced materials at an excellent value-for-money price point, Thursday Boot Company stands out with stylish yet cost-effective footwear solutions that meet both affordability and craftsmanship criteria.”

Are Chelsea boots still in style?

“Chelsea boots are absolutely still in style,” confirms LaGrone. “Both the traditional style and reworked, trendier options are loved by the shoe community.”

What kind of pants should I wear with Chelsea boots?

“Chelsea boots look most flattering when paired with a tapered ankle slack,” says LaGrone. “Of course, for work-boot styles and function, denim pants will often also be paired with Chelsea boots.”

Are Chelsea boots considered formal wear?

“Certain Chelsea boots can certainly be dressed up for more formal occasions such as dinner parties and business events,” says LaGrone. “However, the Oxford loafer remains the most common formal shoe for men's fashion [see our guide to the best loafers for men for more]. If you’re looking for a more formal Chelsea boot, I recommend opting for a glossy leather finish.”