The Brook Taverner Journal

How to Wear Chelsea Boots with Suits, Jeans and Tweeds

Chelsea boots are a staple of a stylish wardrobe and a classic accessory for almost any season or occasion, from casual to formal. These boots are extremely versatile and a streamlined look without laces. Hand-crafted from calf leather, Chelsea boots have an elastic side panel for breathability and a loop of fabric at the back for pulling on the ankle-high boots. The shoes are often found in brown and black, with various shades available in both colours.

Wearing the boots may require a bit of knowledge, but it can be done. In fact, they work well with almost any ensemble, from casual jeans to men’s suits.

A History of Chelsea Boots

Chelsea boots are said to have been designed by J. Sparkes-Hall, a man who created boots for Queen Victoria during the Victorian age. Vulcanized rubber had just been invented by Thomas Hancock and patented in 1844. This rubber helped create the ankle-high boot, giving it the elastic siding we still enjoy today.

Originally created as walking shoes for the Queen, the boots eventually became a staple for both men and women and remained that way until WWI. During this time, a group known as the Chelsea set began travelling along the King’s Road. The group was made of artists, socialists and film directors. Due to their iconic nature, the boots they often wore soon became known as Chelsea boots.

The name stuck, and the shoes became part of the iconic looks of the Beatles, the Mods and even the stormtroopers in George Lucas’s Star Wars trilogy.

How to Wear Chelsea Boots With Suits

A main piece of clothing in any man’s wardrobe is the suit. From black to brown to grey or navy blue, almost any type of suit pairs well with Chelsea boots. This information tends to be a bit surprising to most men who typically wear traditional brogues, oxfords and loafers with their men’s suits. The Chelsea boot provides a different and highly-enjoyable new look.

When choosing the right Chelsea boot for your suit, keep in mind that there are many materials, colours and finishes available in this boot, and some may look better with your suit than others.

The best way to pick out your Chelsea boots is to first determine what suit you’re going to wear. A grey suit works well with brown leather Chelsea boots. If you choose to wear midnight blue or navy suits, however, a darker boot is necessary. Dark brown is an excellent option with blue suits, as it provides a complimentary, smart look. You can also go with black boots if you want to, as these are almost always a safe option with dark blue men’s suits.

How to Wear Chelsea Boots With Jeans

For a casual, dress-down look, Chelsea boots paired with jeans, a tweed jacket or blazer and a tee shirt is the way to go. For the best casual look, opt for the matte or suede finish on your Chelsea boots. For a smart-casual appearance, consider calf leather boots with a high-shine finish.

The colour of boots you want will depend on the colour of the jeans you’re wearing. Blue denim jeans work well with black suede boots or dark brown options. For grey or brown jeans, option for brown Chelsea boots instead.

How to Wear Chelsea Boots With Tweed

Wearing Chelsea boots with a tweed jacket or tweed suits can make an instant statement about your style, as long as you’re wearing the right colour of boots, that is. For this type of outfit, choose brown Chelsea boots in medium or light shades. Burgandy Chelsea boots, which are the most versatile of colours, go with almost any outfit as well. They work well with tweed jackets too.

You can also consider wingtip or captoe Chelsea boots with tweed jackets. These have a bit of a country style to them, which makes it pair well with men’s tweed jackets.

Tips for Wearing your Chelsea Boots


While you can do almost anything in Chelsea boots and wear almost anything with them, there are a few rules you should follow to make sure you always look your best in these types of shoes.

  • When wearing your Chelsea boots with trousers or jeans, keep your trousers over the boot. Do not tuck your jeans into the boots. Not only will this ruin your entire look, but it will also stretch the boot out so that it doesn’t fit you correctly anymore.
  • Suede boots are ideal for a comfortable and casual look. Leather is more formal and smart-casual. Suede is also a wonderful material for eveningwear.
  • Leather is an ideal fabric for every month of the year. It’s going to handle wet weather and snow much easier than suede. If you do opt for suede, clean and apply a protector often to keep the boots lasting as long as possible.

Chelsea Boots Buying Guide


Chelsea boots are close-fitting, so it’s essential that you know exactly what your shoe size is before you purchase on online. Don’t guess; there really isn’t a lot of room for error. If you have to estimate, make sure you’re working with a company that offers a brilliant no quibble return policy like Brook Taverner.

When purchasing Chelsea boots, look for the defining characteristics that make these boots what they are, such as the elastic sides that provide breathability and flexibility. Some boots are sold with zippers on the side instead of elastic and still called Chelsea boots. They aren’t.

Chelsea boots are still popular today because of their classic and simplistic look. They are very versatile as well. You can dress them up by pairing them with men’s suits for a formal look or even dress them down with jeans and a men’s tweed jacket. They work for almost every event and every season of the year. These timeless, classic boots may have been made for walking, but they have come to be so much more.

By Brook Taverner