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Chelsea Boots: A Sizing & Styling Guide

November 27, 2024

chelsea boots in brown, tan and black

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If there is one style of boots we should all have in our autumn and winter wardrobes, it's a pair of classic Chelsea boots. A style icon that has stood the test of time and only grown in popularity, it’s one of the ‘it’ styles to be seen in this season and every season.

So how should you wear your Chelsea boots, how should they fit and when should you wear them? Sit back and relax as we give you the low down on Chelsea boots.

What are Chelsea boots?

Chelsea boots, renowned for their timeless appeal, are a style of ankle boot that seamlessly blends classic and contemporary elements. Throughout time, the Chelsea boot has undergone numerous iterations, with certain attributes evolving from J. Sparkes-Hall’s initial design, notably the pointed toe featuring a black toecap. Today, they have become much more.

Elasticated sides: the hallmark of Chelsea boots is their elasticated sides, a key feature retained from the original design. Positioned over the ankle bone, the U-shaped gusset, in a contrasting colour, enables effortless wearing and removal without having to bend down to tie your laces.

Ankle height: designed to reach just above the ankle, Chelsea boots offer great coverage, making them a favoured choice for country wear and gaining popularity among individuals like horse riders.

Low heels: the traditional heel of Chelsea boots is low, designed with walking in mind rather than featuring the elevated Cuban heel.

Two-part shoes: the Chelsea boot features a two-part construction comprising the front (vamp) and back (quarters) sections, connected near the ankle by vulcanised rubber or elastic (the elasticated gusset). Unlike the Jodhpur boot, the Chelsea boot’s vamp and quarters are sewn in a single seam below the ankle, ensuring durability and longevity.

Rounded plain toe: typically, Chelsea boots boast a round toe and a straightforward, unembellished style—providing a sleek and clean appearance to the vamp. However, certain styles can deviate from this, with chisel square toes and the potential incorporation of a brogue pattern for added detailing.

Pull tugs: for slip-on Chelsea boots, achieving a snug fit is essential. The pull at both the front and rear of the boot, combined with the elasticated sides, helps to put on and remove, ensuring a comfortably snug fit during wear.

Why are Chelsea boots called Chelsea boots?

Chelsea boots are named after the affluent London neighbourhood of Chelsea. These ankle-high boots with an elastic side panel and a loop or tab at the back for easy pulling on were popularised in the mid-19th century. In fact, the boots became particularly fashionable in the Chelsea area during the 1950s and 1960s, worn by the "Chelsea Set," a group of artists, musicians, and trendsetters. Today, Chelsea boots are a classic and versatile footwear choice, remaining popular across various fashion styles.

What is the difference between Chelsea boots and ankle boots?

"Chelsea boots" and "ankle boots" refer to distinct styles of footwear, but there is some overlap in terminology.

Chelsea Boots:

  • Chelsea boots are a specific type of ankle boot characterised by elastic side panels that make them easy to slip on and off.
  • They typically have a sleek and streamlined design with no laces.
  • Chelsea boots often feature a loop or tab at the back to help pull them on.

Ankle Boots:

  • "Ankle boots" is a more general term that includes various styles of boots that cover the ankle but may differ in design and features.
  • Ankle boots can include lace-up boots, zippered boots and those with different closures and embellishments.
  • Unlike Chelsea boots, ankle boots do not necessarily have distinctive elastic side panels.

Ultimately, Chelsea boots are a specific subset of ankle boots, and while all Chelsea boots are ankle boots, not all ankle boots are Chelsea boots.

The Origins of Chelsea boots

The iconic, elasticated Chelsea boot design is credited to Queen Victoria’s personal shoe maker J. Sparkes-Hall, who claimed back in 1851 that the queen herself wore them every single day making them an instant hit with the rest of Great Britain. However, they only became part of mainstream fashion in the 1960s and 70s. These cultural trends helped them become a wardrobe staple.

  • Pop music. The simple Chelsea boot style didn’t really burst onto the fashion scene with a vengeance until the swinging sixties hit London. Worn by models such as Jean Shrimpton and bands such as the Rolling Stones and the Beatles, they were soon the go-to shoe made on the iconic Kings Road area of Chelsea- hence the name.
  • Mod subculture. With the mod scene taking off, trend followers soon adopted this boot style as part of their smart and slick uniform. They became even more popular in 1961, when the Beatles had their very own Chelsea boot style made known as the ‘Beatles Boots’. These boots had a slightly different look to the classic Chelsea design, featuring a pointy toe and high Cuban heel.
  • Star Wars. During the 1970s Chelsea boots had another new lease of life when they made a surprise appearance in the Star Wars trilogy. Worn by Darth Vader’s Stormtroopers, they were in the same style but in the futuristic colour white.

How should Chelsea boots fit?

Chelsea boots are one of the most close-fitting types of footwear, so should fit snugly around your feet. In this quick Chelsea boots fitting guide, follow these three tips to get the perfect fit.

  1. Buy your correct size and no bigger. Chelsea boots are normally true to size, so there’s no need to size up or down. If your Chelsea boots feel too loose, pop on an extra pair of socks.
  2. Check for a gap between the boot and your ankle. The elasticated side panel helps keep this a close fit, so there should be no gap here. Chelsea boots normally come with a handy loop or tab at the back of the boot to enable you to pull them on.
  3. Stretch your boots. If you’re finding it tough getting this close-fitting style on and off and the tab at the back is not helping you, stretch the boots out slightly using a boot stretcher until you find that it is easier to get them on.

How to style Chelsea boots

How to style men’s Chelsea boots:

  • Skinny jeans. Cool and casual, Chelsea boots look fantastic when styled with jeans. Why not pick a tan pair to go with your black skinny jeans for a cool, off the runway look?
  • Boot cut jeans. Not a fan of skinny jeans? Fear not: they look just as good when paired with your regular fit and boot cut jeans. Try suede styles- these will give you a more relaxed vibe.
  • A fitted suit. Bring a retro feel to your look by styling a pair of classic black Chelsea boots with a fitted suit. Don’t forget tan and brown styles can look fantastic against different shades of blue.

How to style womens' Chelsea boots:

  • Leggings and a warm cosy knitted top. It’ll give you an elegant dressed-down look. Mix things up and choose a tan pair, it gives you a real autumnal look that screams style.
  • Fitted trousers and pussybow blouse. This outfit will look super smart for the office when you add a pair of black Chelsea boots. Who said Chelsea boots aren’t formal?
  • A simple shift dress. For the best look, go for a bold colour and add thick tights along with a pair of Chelsea boots. Elegant and stylish, what more could you want?
  • Skater skirt and knitted top. Paired with Chelsea boots, this outfit delivers a glamourous yet grungy look. Chelsea boots don’t always have to be flat- if you’re going out, simply choose a pair with a bit more of a heel.

When should I wear Chelsea boots?

The Chelsea boot’s simple style means they’re really versatile and can be worn for a number of different occasions- at different times of the year. Here are some of the most popular ways to wear your Chelsea boots.

  • Festivals. A more stylish alternative to wellies, Chelsea boots work perfectly at a festival.
  • Work. Super smart and sleek when teamed with a suit, Chelsea boots for the office give you a fashionable look that harks back to the swinging sixties.
  • Weekend walks. If it’s a laidback weekend you’re wearing Chelsea boots for, pair them with skinny jeans and a cosy knit- but don’t forget the edgy leather jacket and winter warmers.
  • Evenings out.For a cute and quirky look on a night out or evening at the pub, Chelsea boots look great teamed with bare legs and a black dress. Add a fedora hat and chunky jewellery to dress the look up.
  • Warm weather. Style your Chelsea boots with frilly ankle socks and bare legs for a throwback Alexa Chung look that never goes out of fashion in the summertime.

How can I take care of my Chelsea boots?

Chelsea boots, primarily crafted from leather, require meticulous care to make them last longer. Follow these steps to ensure your boots remain in optimal condition:

  1. Dampen a cloth with warm, soapy water to gently clean.
  2. Use a circular motion to delicately remove any marks.
  3. Polish with a top-tier black or brown polish for a sophisticated finish.
  4. Employ an old cloth or a soft-bristle brush to erase scratches and marks effectively.
  5. Invest in a good quality shoe horn.

For more boot maintenance, discover our additional tips and advice, from scuff removal to achieving a polished appearance that ensures your Chelsea boots remain both stylish and well-preserved.

Which style of Chelsea boot is right for you?

Finding the perfect Chelsea boot involves considering various factors to align with your style and preferences. Whether you prefer classic leather, suede, or a more contemporary twist, exploring details like heel height and colour will help you decide which Chelsea boot best complements your individual style and taste.

Leather Chelsea boots

Leather Chelsea boots epitomise timeless sophistication. Crafted from high-quality leather, these boots seamlessly blend classic style with modern flair. With their iconic elastic side panels and often sleek silhouette, leather Chelsea boots effortlessly transition from casual to formal occasions. The durability and inherent elegance of leather also make these boots a wardrobe staple for those seeking a polished and refined footwear option.

Brogue Chelsea boots

Brogue Chelsea boots combine the classic appeal of brogue detailing with the iconic Chelsea boot silhouette. The addition of perforations and intricate patterns along the toe cap and sides elevates these boots, adding a touch of sophistication to a timeless design. Brogue Chelsea boots are ideal for those seeking a blend of traditional craftsmanship and contemporary style. They offer a unique and fashionable twist on a classic footwear choice, seamlessly merging formal and casual designs.

Suede Chelsea boots

Suede Chelsea boots exude a luxurious and tactile elegance, offering a softer alternative to traditional leather. The velvety texture of suede adds a touch of refinement to the iconic Chelsea boot silhouette. Ideal for transitional seasons, suede Chelsea boots effortlessly bridge the gap between casual and sophisticated styles. Their versatility allows them to complement a range of outfits, making them a stylish choice for those seeking comfort and style in their footwear collection.

Check out the shoezone blog for more style tips and footwear suggestions for every occasion.