Tips on How to Style Chelsea Boots for Women for All Types of Outfits

A member of the Wardrobe Oxygen community reached out asking for tips on how to style Chelsea boots for women. She wanted the style and convenience of these classic pull-on boots, but wasn't exactly sure what to wear with them. Chelsea boots are comfortable, practical, and I will show below that they can also be quite versatile offering tips on how to style them for a range of different kinds of outfits.

This post was originally published in 2015… a whole decade ago! When I was asked this question, I went into my archives and decided instead of recreating the wheel, updating the content I already had. I must admit this is a complete overhaul as fashion has changed more than we realize in the past 10 years. That being said, Chelsea boots are still as stylish as ever.

What are Chelsea boots?

Chelsea boots are ankle-length boots with elastic side gussets, a low heel, and a snug fit around the ankle. Chelsea boots also often feature a loop or tab of fabric on the back of the boot, allowing the boot to be pulled on easily.

The design is credited to Queen Victoria's shoemaker, Joseph Sparkes Hall. Hall called them J. Sparkes Hall's Patent Elastic Ankle boots and claimed that “She (Queen Victoria) walks in them daily and thus gives the strongest proof of the value she attaches to the invention”. Because of Queen Victoria's love of these boots, they became popular for horseback riding as well as walking.

Charles Goodyear's development of vulcanized rubber enabled this style of boots to feature elastic gussets or panels, making them easier to slip on and off. By the late 1840s, these boots were the primary boot style in the West.

In the mid-1950s, Chelsea was a hub of fashion and culture and those fashionable folk in that area were known as the ‘Chelsea set.' The Chelsea set were known for their stylish and avant-garde fashion and lifestyle choices, and those looks often included this style of boot. Hence, the boots became known as Chelsea boots.

These boots are often also known as Beatle boots, as they were worn by rock stars such as The Rolling Stones and The Beatles. You will find Chelsea boots in a range of colors, sole thicknesses, toe shapes, and textures, but they will always have the trademark elastic side panels.

How to Style Chelsea Boots for Women

Chelsea boots are a great addition to a wardrobe for their versatility and fantastic combination of trendiness yet classic style. They look modern but will still be wearable for years to come. Below are five ways to style Chelsea boots to show you don't need a big shoe wardrobe to have big style and plenty of versatility!

Style Chelsea Boots with Short Dresses and Skirts

Chelsea boots look surprisingly chic with short dresses and skirts. To achieve a long leg line, have your boots match the same color as your hosiery, or choose boots that are low contrast to your skin tone. That being said, right now it's very on trend to have a statement boot, so don't be afraid to have fun with color and metallics; you'll be surprised how versatile a white or silver boot can be!

Shop the look: sunglasses | earrings | dress (00-16) | bag | socks | boots

Socks are back, and having a hint of sock peeking out from the top of your Chelsea boots, paired with bare legs or even sheer hosiery, is a modern option. Keep your ensemble simple and clean so the effect is modern, not twee.

Style Chelsea Boots with Midi-length Dresses and Skirts

Chelsea boots are a modern option to pair with the trendy midi-length skirts and dresses that have been popular the past few years. A skirt with volume (pleats, chiffon layers, bubble, stiffer fabrics like poplin) will be well balanced with a classic Chelsea boot. If you choose to wear a Chelsea boot with a slip skirt, you may desire a higher shaft so the skirt doesn't get caught in the boot opening.

Shop the look: top (XXS-XXL) | skirt (XXS-XXL) | necklace | earrings | bag | boots

Again, you can go with tights in the same color as your boots, or have a hint of sock peeking out of the top to add a “luxe grunge” vibe to your midi skirts and dresses. Do not be afraid to layer socks over hosiery for a contemporary effect.

Style Chelsea Boots with Cropped Pants and Ankle Jeans

A way to winterize your cropped and ankle-length jeans and pants is to pair them with Chelsea boots. To make the look feel purposeful, you need either 1/2″ of skin showing between the boot and the pant hem, or 1/2″ of pant hanging over the boot for a continuous line. Cuffing jeans to achieve this length can look quite stylish.

Shop the look: sweater (XXXS-3XL) | pants (XS-XXL & petite/tall) | sunglasses | lip gloss | necklace | bag | boots

For straight and narrow cut pants and jeans, you can use a sock to fill the space between the hem and the boot top. For wide-leg cropped pants and jeans, it's better to have skin showing or have the pants cover at least the top 1/2″ of the boot.

This is a chance to have fun with texture. Frayed jeans, cuffs, textured socks, and colorful boots (or boots with colorful soles) can add personalty and style to a simple denim-based ensemble.

Style Chelsea Boots with Full-Length Flare and Bootcut Jeans

Chelsea boots are made for full-length jeans and look best with flare and bootcut styles. Especially with lug soles and bulbulous toeboxes, Chelsea boots make jeans with a flared hem look balanced and modern.

shop the look: blouse (0-20/22) | jeans (00-32) | belt | bag | boots | earrings

Go with a chunky style, or sleek; both work well with full-length, flare, and bootcut jeans. Just be sure if the Chelsea boot is low profile, it has a long enough toebox to have it clearly protrude from the hem of your jeans.

Your jeans should be long, almost touching the ground to 3/4″ from the ground. When you cross your legs, you should not see your shins; if that happens, consider wearing socks or hosiery in the same color as the boot for a continuous line.

Style Chelsea Boots with Wide Leg Trousers

Chelsea boots pair well with both wide-leg trousers and jeans. Chelsea boots can be stiff and heavy, and therefore look best with sturdier fabrics like wool, twill, ponte, and denim.

Shop the look: tee (XS-3X & tall/petite) | jeans (XS-3X & petite/tall) | scarf | boots | bag | earrings | lipstick

Again, keep the pants long where the hem is just above the ground to 3/4″ from the ground. And again, choose a style of Chelsea boot that is either long or sturdy enough to be seen beyond the wide hem of your jeans or pants.

Style Chelsea Boots with Leggings and Skinny Jeans

Chelsea boots can modernize your existing collection of leggings and skinny jeans. Take a cue from Gen Z and have contrasting socks peek out of the boot and the leggings tucked into the sock.

Shop the look: blazer (00-24 & petite) | tank (XXS-XXL) | jeans (00-40 & lengths) | bag | necklace | earrings | boots | sunglasses

For skinny jeans and jeggings, you can have the socks be hidden and tuck the hem into the boot, or cuff the skinny jeans so it hits at the top of the boot, with or without a visible sock.

I hope these five outfits give you some sartorial inspiration on how to style Chelsea boots in a new and fresh manner.

If you purchase quality Chelsea boots and take good care of them (take them to the cobbler to be reheeled and resoled as necessary, have a day between wearings so they don’t get stretched out or stinky, polish and protect the leather), this is the kind of shoe you can have in your wardrobe for over a decade.