Tanisha Angel

11 Best Chelsea Boots for Men | Man of Many

An Aussie icon, R.M. Williams has been making some of the best quality Chelsea boots anywhere in the world. The brand offers a range of streamlined, slip-on footwear that is ideal for any situations, whether its black Chelsea boots with a suit or with your favourite pair of ripped jeans.

1. R.M. Williams

Sydney based premium sneaker brand Monochrome takes a modern approach to the classic Chelsea boot style. This iteration sees a tennis outsole in place of the traditional heal. The Olive green suede upper combines with the Grey Margom rubber outsole to create a contemporary view on a classic design with modern functionality. All Monochrome shoes are handcrafted in Italy from premium Italian full-grain leathers and suedes. In fact, all of the raw materials are sourced from within Italy and are made in the famous Le Marche region, known for its history in shoemaking. These are the best Chelsea boots for the man who wants to be stylish no matter the occasion.

2. MONOCHROME Chelsea Sneaker

Made from healthy, eco-friendly leather, Astorflex offers a collection of stylish, classic shoes and its Chelsea boots are among the brand’s finest. The ultra-comfortable boots are made using high-end Italian construction for a superior fit.

3. Astorflex

Best-known for its low-top minimalist sneakers, Common Projects has branched out in recent years, offering some of the best Chelsea boots on the market. If you are wondering how to wear Chelsea boots, you can take a sneaker approach with the Common Projects, styling them with jeans for a streetwear vibe. After all, no man’s outfit is complete without the iconic Common Projects embossed lettering on the heel.

4. Common Projects

This British footwear brand offers some of the most high-class Chelsea boots men can buy. The fine leatherwork captures some of the classic working-class construction the brands style is renowned for.

5. Church’s

Renowned for using the highest quality materials for its footwear, Salvatore Ferragamo has collated a collection of Chelsea boots that bears no exception. The expert craftsmanship is on display in this range of timeless shoes. Complement your outfit with the high-end collection.

6. Salvatore Ferragamo Chelsea Boots

With a story that starts in the 1800s, Blundstone knows a thing or two about making great boots. The Tasmanian family business has a collection of Chelsea boots men simply can’t get enough of. Reliable, durable and stylish, these are some of the best Chelsea boots Australia has produced.

7. Blundstone

For the Chelsea boots outfit that is a little more adventurous, Paul Smith is our go-to. The elegant and fashion-forward footwear incorporates sophisticated takes on the timeless silhouettes, with a few cheeky colour combinations thrown in.

8. Paul Smith

A classic Chelsea boots outfit needs a classic brand and there is none more iconic than Dr Marterns. Best-worn by the punks and beatniks of the 1970s British underground, this silhouette is as suited to the recording studio as it is the boardroom.

9. Dr Martens

Made in Italy, Scarossa boots combine the old-school shoemaking philosophy with modern design and sustainable practices. The artisanal techniques and luxury materials make the Scarossa Chelsea boots a great option.

10. Scarosso

These boots were made for stomping. The Alexander McQueen Chelsea boots are designed for the modern man.

11. Alexander McQueen

Chelsea boots are a laceless shoe designed to slip on and off the foot. Traditionally, they are comprised of two parts; the vamp and the quarters, each constructed from a single piece of leather. The vamp and the quarters meet at the ankle, where they are connected by an elastic or vulcanised rubber gusset which extends to just below the ankle. These boots typically have rounded toes and low heels, and often feature a small heel tab designed to pull the boot on and off with ease.

What is a Chelsea Boot?

A quintessentially English footwear style, Chelsea boots date back to the Victorian era. They were invented in 1851 by J. Sparkes-Hall, a bootmaker for Queen Victoria, and were worn by both men and women. The boots were originally invented as riding boots, later forming an element of the British mod movement, thanks to them being co-opted by The Beatles during the 1960s.

History of the Chelsea Boot

The two main materials used for boots are leather and suede. Leather Chelsea boots are a versatile option and can be dressed up or down; their sleek aesthetic working synergistically with the boots’ simple silhouette. If you wondering how to wear Chelsea boots, the black leather version is a refined option that can even be worn with semi-formal and formal outfits in lieu of dress shoes, while the brown leather variety works well with casual, smart casual, and semi-formal looks.

Types of Chelsea Boots

Both leather and suede Chelsea boots can be worn for casual looks, though suede gives off a more relaxed vibe. Chelsea boots and jeans make for a chilled, pared-back look; opt for slim-cut jeans over skinny or straight leg varieties, as this will ensure the hem of your jeans sit nicely over the top of the boot without constricting or drowning it. You can also try cuffing or pin-rolling your jeans to get the most out of your Chelsea boots outfit.


Their sleek, minimalistic silhouette allows Chelsea boots to be worn for smart casual outfits. Both leather and suede boots can be worn in a smart casual outfit, however black leather is always a safe bet. A pair of black leather Chelsea boots can add a sense of refinement to classic outfits like a roll neck or mock neck sweater, black jeans or chinos, and an overcoat.

Smart Casual

Chelsea boots needn’t be relegated to weekend wear; their versatility allows them to be worn throughout the week with business casual outfits. When wearing them to work, opt for a simple silhouette in black or brown leather and team your boots with office-appropriate separates, like slim-cut chinos, an oxford shirt or thin roll-neck sweater, and a blazer or structured coat.

Business Casual

Their sleek appearance allows Chelsea boots to be incorporated into the modern man’s semi-formal attire. Chelsea boots make an ideal footwear alternative to derby shoes, monk straps, and loafers, and can easily be worn with a suit. Like with semi-formal attire, stick to leather varieties. To add a sophisticated touch to your Chelsea boots outift, you can even opt for a pair in dark brown or black patent leather.


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