Chelsea Boots for Men

What is a Chelsea Boot?

Also referred to as “dealer boots”, men’s handmade Chelsea boots are close-fitting ankle-high boots that feature an elastic panel on either side of the shoe. They are a sleek pair ideal for both formal and informal occasions. The shoes can either be dressed up or down depending on one’s preference.

Why are they called Chelsea boots?

In the 1950s and '60s, Chelsea boots had become quite popular in Western London. With time, everyone from the streets in Chelsea, such as Jean Shrimpton and Rolling Stones, started wearing them. The name "Chelsea" was therefore adopted.

History of the Chelsea Boot

The Chelsea boot is a classic country wear that can be dated back to the Victorian era. Evidence suggests that the first one to exist was designed by Mr. J Sparkes-Hall, queen Victoria’s bootmaker back in 1837. Mr. J Sparkes-Hall also added fabric tabs and a small heel to make them easier for the queen to wear.

However, the Chelsea boot would not have been birthed without the vulcanized rubber that had been invented by Charles Goodyear years before. Mr. J. Sparkes used this elastic rubber that was put on the side ankles to make the shoes more comfortable.

The shoe continued to gain popularity and was then adopted by equestrians, who named it the "paddock boot.” It has since then remained to be an essential shoe staple in every man's arsenal.

What Makes Chelsea Boots Different?

While the stylish  Chelsea boots for men have almost similar features with the jodhpur boots, they differ in the following ways;

  • They not only have round toes but lower heels.
  • Chelsea boots made from genuine leather feature vamps and quarters that are sewn together in one place, slightly below the ankle. Additionally, the quarters and vamp that meet around the ankle are held together by a strip of vulcanized elastic.
  • While the strip of elastic in Jodhpur boots goes all the way down to the sole, the elastic piece in Chelsea boots only extends near the ankle, just above the welt.

Chelsea Boot Colors

A pair of cool Chelsea boots for men is a versatile fashion statement that comes in several variations, like the slim soled and thick-soled. In terms of color, black or brown, for instance, pair well with regular closet staples like suits, stylish jeans, and a knit tie.

If you are in search of a color that is all-round, then consider going for burgundy. The color can be paired with just about anything. You can also opt for exotic colors such as red or blue as they tend to make a statement about your outfit.

Should I Go for A Smaller Fit?

Well, for comfortable handmade men’s  Chelsea boots, you don't have to size up or down as the shoes are mostly close fit and generally true to one's size. However, in case they end up feeling loose, you can always wear them with a pair of lightweight socks. The relatively thin merino socks, for instance, work great.

To Cuff or Not to Cuff?

When wearing Chelsea boots with jeans, always ensure that your skinny jeans do not cover the boots. The jeans should always be above. Some people also like to cuff their ripped jeans to make their shoes visible. I wouldn't recommend this style, though, as cuffed jeans always end up ruining your entire look.

The other tip is to avoid tucking jeans into your Chelsea boots as they end up loosening the elastic pane. You don't want to walk around with a pair that doesn’t fit properly, do you?

What Should I Wear with My Chelsea Boots?

Handmade Chelsea boots as a functional wardrobe staple can be styled in different ways.

  • Short Chelsea boots- Go for fashion-forward outfits such as wide-legged trousers.
  • Brown Chelsea Boots-   Consider options such as lighter shades of straight-legged jeans, paired with a polo shirt. Additionally, for a more casual look, try pairing them with white denim.
  • If you want to create a more casual look, then go for a dark brown suede pair and dress them down with a charcoal suit of your choice.
  • Wingtip Chelsea boots- Though more casual than plain, authentic wingtips can be dressed down with both suits and jeans. If you want to look more stylish, then pairing them with a genuine leather jacket can be a good idea.
  • Black Chelsea boots-I wouldn't recommend dressing them down with a tuxedo. Instead, opt for staples like dress shirts, pleated pants, or even suits of darker shades such as navy.

Cool Chelsea boots for men can be tailored to suit your style for any upcoming occasion. With unique comfort features and simple styling options, you cannot afford to miss a pair. Get your hands on a unique pair now from RebelsMarket at an affordable price.


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