How to Style Chelsea Boots: 15 Great Styles for Inspiration!

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Chelsea Boots have been around in some form since the 1830s in England, though they took the world by storm during the British Invasion of rock bands of the 1960s.

In this article, I am going to look at what makes Chelsea boots so iconic. And with the help of our Expert Stylist and Fashion Writer Danielle McKenna, I’ll explore how to style Chelsea boots.


Contents

Meet the Experts: 

  • Danielle McKenna – Expert Stylist & Fashion Writer of over 200 published articles on fashion, beauty, and health trends 

A Brief History of Chelsea Boots

In 1837, Queen Victoria requested a boot be made without laces because the laces kept getting stuck in the stirrups while she was riding. Not only was it the laceless new design that made these a breakthrough in boot fabrication at the time, the vulcanized rubber that was used to create the side panels for which the Chelsea boot is now famous and instantly recognizable, allowed the wearer to slip them on and off easily.

Originally called “Paddock Boots” and worn by both men and women, they didn’t inherit their “Chelsea” name until they became super popular in the 50s and 60s. They became associated with the fashion of the King’s Road in Chelsea, London which is where they inherited the name we now all know them by.

The British Invasion brought their fashion to the US and the Chelsea boot was made iconic by people like The Beatles, The Rolling Stones, and Jean Shrimpton.


How to Style Chelsea Boots: 15 Ideas for Inspiration

I’ve put together 15 of our favorite ways to style Chelsea boots for your inspiration.

1. Jeans and a Midi Length Coat

Credit: Instagram / vabotti_de

This is a classic pairing that will never steer you wrong. The long vertical lines of this ensemble will elongate the torso and make you appear taller. You can wear boot-cut, skinny or straight-leg jeans, just as long as the leg is not too wide or flares out too much.

This is how you can create this look:

PAIGE Women's Hoxton High Rise Ultra Skinny Fit Raw Crop Jean, Atterbury w/Torn Hem, 26
PAIGE Women's Hoxton High Rise Ultra Skinny Fit Raw Crop Jean, Atterbury w/Torn Hem, 26
Crafted in our TRANSCEND VINTAGE denim authentic character and sublime softness.; Front Rise: 10"
$225.00 Amazon Prime
Madden Girl Women's Tessa Chelsea Boot, Black Paris, 10
Madden Girl Women's Tessa Chelsea Boot, Black Paris, 10
Madden Girl; Chelsea Boot with Round Toe; Chunky Tread Sole; Block Heel; Tonal
$59.79 Amazon Prime

2. Down Parka and Black Stretch Denim Leggings

Credit: Instagram / glamilatvija

This is a super easy-to-wear sporty outfit for the woman on the go. You don’t have to stick with black, although you know you can never go wrong with black. But if you are going to wear patterned leggings, Danielle McKenna suggests “a good general guideline is to make sure one of the colors in the leggings matches your boots.”

This is how you can create this look:

Floerns Women's High Waist Stretchy Raw Hem Skinny Leggings Denim Pants Black L
Floerns Women's High Waist Stretchy Raw Hem Skinny Leggings Denim Pants Black L
Fabric has high stretch; Feature: High waist, button fly, cropped denim pants; Suitable for holiday, dating, weekend, travel, going out, vacation, casual wear, summer
Sam Edelman Women's Laguna Chelsea Boot Black 8 Medium
Sam Edelman Women's Laguna Chelsea Boot Black 8 Medium
Sam Edelman's Iconic Laguna Chelsea Boot; Heel Height: 1.5 inches; Boot Shaft: 5.75; Boot Leg Circumference: 9.45 inches
Amazon Prime

3. Blazer and Jeans

Credit: Instagram / morenamiashoes.mx

A blazer can take any style up a notch from super casual and is perfect for date nights or drinks out with the gals. If your casual Fridays at the office are not casual enough for jeans, just swap out the jeans for a pair of tapered slacks and you’re good to go.

This is how you can create this look:

Sale
Signature by Levi Strauss & Co. Gold Label Women's Totally Shaping Pull-on Skinny Jeans (Available in Plus Size), Sun Worshipper Signature, 2 Medium
Signature by Levi Strauss & Co. Gold Label Women's Totally Shaping Pull-on Skinny Jeans (Available in Plus Size), Sun Worshipper Signature, 2 Medium
Inseam: 27"= Short, 29"= Medium, 31"= Long; You may also like Totally Shaping Pull on Bermuda Shorts
$17.71 Amazon Prime
Sale
Steve Madden Women's Barclay Fashion Boot, Black Leather, 6
Steve Madden Women's Barclay Fashion Boot, Black Leather, 6
Steve Madden Womens; Women's lug sole fashion boot; Back and front pull tabs for easy on and off
$59.86 Amazon Prime
Fossil Women's Kinley Leather Small Crossbody Purse Handbag, Black (Model: ZB7878001)
Fossil Women's Kinley Leather Small Crossbody Purse Handbag, Black (Model: ZB7878001)
Genuine Leather Crossbody Bag; Zipper Closure with Hidden Magnetic Snap; imported; Measurements: 8.63"L x 2.5"W x 7"H; 1 Adjustable Crossbody Strap
$150.00 Amazon Prime

4. Plaid Mini Skirt & Turtle Neck

This is the epitome of fall and winter fashion. When the weather gets really cold, opt for sheer tights and a waist-length jacket. Almost any jacket that rests at the waistline will look good with this outfit, whether it’s a lined denim jacket, leather biker jacket, or puffer jacket.

Alternatively, you could opt for a midi or maxi-length wool trench. If you’re going for a midi-length coat, make sure the hem of your coat falls below the hem of your skirt.

This is how you can create this look:

Sale
Amazon Essentials Women's Classic-Fit Lightweight Long-Sleeve Turtleneck Sweater (Available in Plus Size), Black, Large
Amazon Essentials Women's Classic-Fit Lightweight Long-Sleeve Turtleneck Sweater (Available in Plus Size), Black, Large
CLASSIC FIT: Close but comfortable fit with easy movement.; DETAILS: Features a fold-over turtleneck, rib detail at neck, cuffs, and hem.
$17.00 Amazon Prime
No nonsense Women's Super Opaque Control-Top Tights, Black/Black, Large
No nonsense Women's Super Opaque Control-Top Tights, Black/Black, Large
2 pair pack; Panty: 81% Nylon, 19% Spandex; Leg: 89% Nylon, 11% Spandex; Pull On closure; Hand Wash Only
$14.99 Amazon Prime
Sale
Blowfish Malibu Women's Redsen Faux Leather Chelsea Ankle Boot, Black, 8.5
Blowfish Malibu Women's Redsen Faux Leather Chelsea Ankle Boot, Black, 8.5
Synthetic upper with ruching at vamp; Ankle-high Chelsea bootie shaft with elastic ribbed side goring
$36.08 Amazon Prime
Calvin Klein Gabrianna Novelty North/South Key Item Tote, Caramel
Calvin Klein Gabrianna Novelty North/South Key Item Tote, Caramel
High quality vegan leather; Tote with removable interior wristlet pouch
$64.82 Amazon Prime

5. Belted Wrap & Leggings

Credit: Instagram / izzyscloset_x

You can swap out the leggings for black skinny jeans, too. If the boots aren’t black, and you don’t want them to be the focus of your outfit, they should really either match the leggings or at least be in the same tonal range as something else in the outfit.

Here’s how we would put this outfit together:

MakeMeChic Women's Faux Leather High Waist Split Straight PU Leather Skinny Pants Coffee Brown M
MakeMeChic Women's Faux Leather High Waist Split Straight PU Leather Skinny Pants Coffee Brown M
Fabric has slight stretch, comfortable to wear; Occasions: suitable for work, business, dating, weekend casual and daily wear
$37.99 Amazon Prime
SweatyRocks Women's Solid Plain Long Sleeve Ribbed Knit Pullover Crop Tee Tops Black S
SweatyRocks Women's Solid Plain Long Sleeve Ribbed Knit Pullover Crop Tee Tops Black S
RUN SMALL,Please refer to size measurement in products description before ordering.Thanks; Boat neck,ribbed knit,basic long sleeve crop top,cut hem

6. Pant Suit with a Wool Trench

Credit: Instagram / fallingfora

This is a great outfit for work or any situation that calls for something a little less casual than jeans or leggings. If you have a wider leg on your pantsuit, don’t tuck your pants into your boots.

Let them fall over, otherwise, they will bunch and pull awkwardly when you’re moving around.

This is how you can create this look:

Women's Business Suit Set Lady Long Sleeve Single Breasted Open Front Office Blazer Split Front Pants Two Piece Outfits Black
Women's Business Suit Set Lady Long Sleeve Single Breasted Open Front Office Blazer Split Front Pants Two Piece Outfits Black
SIZING and LENGTH: If you're in between sizes, we recommend ordering a size up.; Wash: Hand Wash Cold / Do Not Bleach / Hang Or Line Dry
Sale
Women's Formal Work Wear White Simple Shirt (225 Light Blue, XS)
Women's Formal Work Wear White Simple Shirt (225 Light Blue, XS)
Button down shirt blouse for women.
$17.56 Amazon Prime
Sale
ANRABESS Women's Casual, Pinklish Khaki, Small
ANRABESS Women's Casual, Pinklish Khaki, Small
Size - S=US(4-6),M=US(8-10),L=US(12-14),XL=US(16-18) ,see details in rich description.; Wash - Hand wash / Do Not Bleach / Dry Flat / Do not iron.
$46.99 Amazon Prime
CUSHIONAIRE Women's Pax high pull on chelsea boot +Memory Foam, Black 6.5
CUSHIONAIRE Women's Pax high pull on chelsea boot +Memory Foam, Black 6.5
Premium Vegan Leather upper; Pull tab for Easy Slip on / off; Premium Memory Foam Insole; Durable long lasting outsole
$49.99 Amazon Prime

7. Slacks, Button Down Shirt, Sweater with a Long Peacoat

Credit: Instagram / angharadbjones

Androgyny and Academia come together to create this ensemble. Don’t be afraid to cuff your slacks if they have a straight or wider leg to give it a bit more of a laid-back vibe, and of course to show off your boots!

This is how you can create this look:


8. Oversized Belted Jacket & Faux Leather Leggings

Credit: Instagram / franki.dammone

Because Chelsea boots go with just about any casual outfit and can also be moderately dressed up, this is a perfect example of how just some accessories can completely change an outfit. The bright green beanie and oversized hobo handbag give this ensemble a super casual look.

You can take the same outfit, lose the beanie, add a pair of swanky sunglasses and switch the hobo bag for a sleek black tote, and all of a sudden, you go from funky super casual to smart casual.

Danielle McKenna advises that “if you’re going to wrap and belt an oversized jacket, instead of going with a stiff blazer, maybe try something that’s made out of material that is a little more forgiving and pliable, so you don’t have things like pocket flaps jutting out.”

This is how you can create this look:


9. Midi Dress with Cropped Denim Jacket

Credit: Instagram / buenocanada

Chelsea boots lend a cool edge and vintage feel to any basic midi dress. Top it off with a slim-fitting cropped jacket, and of course a pair of Chelsea boots to balance out the look.

This is how you can create this look:


10. Oversized Turtleneck and Shacket

Credit: Instagram / lmer_

Nothing says comfortable style like an oversized turtleneck and they are everywhere this season. When the mercury plummets, add an oversized shacket (shit/jacket). 

This is when it all becomes a balancing act to even out proportions. If you are going voluminous on top, Danielle McKenna recommends you “make sure you stick with a skinny or slim fitting straight leg on the bottom so you don’t look like you’re drowning in fabric.”

Adding a pop of color to the browns and beiges of the season is a great way to add a little wow.

This is how you can create this look:

Lucky Brand womens Mid Rise Ava Skinny Jean, Waterloo, 30 US
Lucky Brand womens Mid Rise Ava Skinny Jean, Waterloo, 30 US
FIT: Mid-rise, slim fit with a skinny leg; Classic 5-pocket styling; Zipper fly closure; Front rise: 9 inches, Leg opening: 10 inches (Size 27)
PRETTYGARDEN Women's 2024 Plaid Shacket Jacket Casual Button Wool Blend Winter Tartan Trench Coat With Pockets (Red,Medium)
PRETTYGARDEN Women's 2024 Plaid Shacket Jacket Casual Button Wool Blend Winter Tartan Trench Coat With Pockets (Red,Medium)
Made of lightweight, soft-touch polyester fabric for comfortable wear; Features long sleeves, button closure, notched lapels, and loose boyfriend fit
$54.99 Amazon Prime

11. Deep Jewel Tones Over Black Skirt, Tights, and Chelsea Boots

Credit: Instagram / style_conscience

This is a super easy-to-put-together look that is both stylish and comfortable. Black Chelsea boots, black tights, and a black mini are topped with a deep ruby red long-sleeved top.

This outfit would work equally well for fall and winter with any deep jewel tone, like a deep sapphire blue, amethyst purple, or emerald green.

This is how you can create this look:

Hanes Women's EcoSmart Blackout Tights, Black, Large
Hanes Women's EcoSmart Blackout Tights, Black, Large
Environmentally-friendly garment without sacrificing design or allover comfort; Includes Static Resist to help reduce embarrassing cling
$16.00 Amazon Prime

12. Cropped Puffer and Wide Straight Leg Jeans

Credit: Instagram / saaara57

It’s no secret why Chelsea boots are the perfect accompaniment to androgynous looks as they are worn by both men and women. The simplicity of this look is what makes it not only wearable by both guys and gals but also stylish for both.

This is how you can create this look:


13. Leggings and Comfy Socks with an Oversized Sweater and Midi Puffer

Credit: Instagram / marissawearsanoutfit

One of the big trends in über-comfort, stylish looks is the wooly socks pulled up and bunched over the top of the boot. You can create this look with any slim-fitting pants that you tuck into your boots.

Then add to that a wooly sweater and a midi puffer for colder days and you’ve got yourself a great outfit.

This is how you can create this look:


14. Midi Skirt and Cropped Jacket

Credit: Instagram / blundstoneusa

Don’t be fooled into thinking that you can only wear your Chelsea boots with pants. They look great with skirts and dresses, too. Try a high-waisted midi skirt and turtleneck with a cropped biker or even denim jacket.

This is how you can create this look:

Sale
Amazon Essentials Women's Classic-Fit Lightweight Long-Sleeve Turtleneck Sweater (Available in Plus Size), Camel Heather, Medium
Amazon Essentials Women's Classic-Fit Lightweight Long-Sleeve Turtleneck Sweater (Available in Plus Size), Camel Heather, Medium
CLASSIC FIT: Close but comfortable fit with easy movement.; DETAILS: Features a fold-over turtleneck, rib detail at neck, cuffs, and hem.
$22.40 Amazon Prime
Verdusa Women's Plaid Print High Waist Casual A Line Flared Midi Skirt Brown XS
Verdusa Women's Plaid Print High Waist Casual A Line Flared Midi Skirt Brown XS
Feature: high waist, plaid print, zipper closure, flowy skirt, below knee length; Soft fabric has no stretch
Sale
Levi's Women Faux Leather Belted Motorcycle Jacket (Standard and Plus Sizes), Black, Large
Levi's Women Faux Leather Belted Motorcycle Jacket (Standard and Plus Sizes), Black, Large
Adjustable zipper cuffs and removable belt at hem; Levi's red tab on lower left side seam; Two lower welt zipper pockets and one smaller lower welt zipper pocket on right side
$46.51 Amazon Prime
Blundstone Women's 1351 Chelsea Boot, Rustic Brown, 5 UK/8 M US
Blundstone Women's 1351 Chelsea Boot, Rustic Brown, 5 UK/8 M US
Anatomically shaped removable footbed; Steel shank; Poron xrd shock protection in heel-strike zone
$219.95 Amazon Prime

15. Cropped Sweater, Long Shirt, and Hip Length Jacket with a Scarf

Credit: Instagram / michel_nadeau_

Here’s a great example of that ‘looking put together without even trying’ aesthetic. The secret is layering at different lengths, combined with different textures that balance everything out and pull the whole outfit together.

This is how you can create this look:

Signature by Levi Strauss & Co. Gold Label Women's Modern Straight Jeans, cape town, 16 Medium
Signature by Levi Strauss & Co. Gold Label Women's Modern Straight Jeans, cape town, 16 Medium
Inseam: 29"= Short, 31"= Medium, 33"= Long; Available in extended sizes; Premium quality, super stretchy denim
$27.99 Amazon Prime
SweatyRocks Women's Solid Pullover Top Crewneck Long Sleeve Cropped Sweatshirt Grey L
SweatyRocks Women's Solid Pullover Top Crewneck Long Sleeve Cropped Sweatshirt Grey L
Material: 35% Rayon, 60% Polyester, 5% Spandex; Comfortable and Breathable to wear; Wash Recommended With Cold Water / Do Not Bleach / Hang Or Line Dry
$25.99 Amazon Prime
Sale
Allegra K Women's Notched Lapel Double Breasted Pea Coat X-Small Grey
Allegra K Women's Notched Lapel Double Breasted Pea Coat X-Small Grey
The notched lapel collar adds a stylish and structured element to this coat; H Line, Long Sleeves, Fully Lined, Belt Cuffs
$69.99 Amazon Prime
Sale
Soda Pilot ~ Women Lug Sole Low Heel Chelsea Fashion Ankle Bootie w/Double Elastic Gore (GREY NUBUCK, us_footwear_size_system, adult, women, numeric, medium, numeric_5_point_5)
Soda Pilot ~ Women Lug Sole Low Heel Chelsea Fashion Ankle Bootie w/Double Elastic Gore (GREY NUBUCK, us_footwear_size_system, adult, women, numeric, medium, numeric_5_point_5)
Latest Fashion and Trend for Stylish and Sexy look; Platform measures approximately .75", Shaft measures approximately 5.5”
$28.00 Amazon Prime

Are Chelsea Boots In Style 2024?

Almost every style of ankle boot you can imagine is on trend for 2024. From kitten pumps and stilettos to combat boots, hiking boots, western-style ankle boots, and moon boots, Chelsea boots, of course, being among them.

We are seeing a lot of over-the-top boot silhouettes all over the place at the moment, some of which are reminiscent of something Mickey Mouse might wear. From the bulbous toes to the exaggerated platform, not to mention that apparently “ugly” shoes and boots are in, celebrities and influencers are embracing the ugly ducklings of the ankle boot world.

But for how long?

Unless you have loads of disposable income and are planning to get yourself a new pair of boots next season because NO one is wearing the style that is so last season, Danielle McKenna suggests you “avoid the runway one-trick-ponies and stick with the styles that straddle the fence between trendy and timeless to avoid having to constantly update your wardrobe.”

This is one of the reasons we love Chelsea boots. They are both trendy and timeless and will never go out of style.


Take Away

Chelsea Boots are timelessly stylish. And although I’ve shown you 15 great ways to wear them, they will go with almost any casual to smart-casual outfit.

Chelsea boots are one of the most versatile types of casual footwear you’ll own, and can be styled out to be funky and edgy or relaxed and even a little conservative.

So whether you were looking through the outfits we put together because you already have a pair of Chelsea boots and weren’t quite sure what to wear with them, or you were thinking about getting a pair, there’s nothing stopping you now from rocking these must-have fall and winter closet staples.

Written by Jacqueline Ames

Jackie is the resident fashion and nail design guru at Luxe Luminous. With a degree in Management and a deep-seated passion for the glamorous styles of the 50s and 60s, Jacqueline offers a unique fusion of business acumen and vintage fashion flair in her captivating articles.