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

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.

Credit: Instagram / vabotti_de

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
Amazon Essentials Women's Long-Sleeve Lightweight Crewneck Sweater (Available in Plus Size), Oatmeal Heather, Large
Amazon Essentials Women's Long-Sleeve Lightweight Crewneck Sweater (Available in Plus Size), Oatmeal Heather, Large
Close-but-comfortable fit with easy movement; Lightweight and soft yarn; Crew neckline; Ribbing at collar, cuffs and hem
Sale
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
$66.24 Amazon Prime

2. Down Parka and Black Stretch Denim Leggings

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.”

Credit: Instagram / glamilatvija

This is how you can create this look:

Sale
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
$19.99 Amazon Prime
Orolay Women's Thickened Down Jacket (Beige, XX-Small)
Orolay Women's Thickened Down Jacket (Beige, XX-Small)
Shell/Lining Fabric: 100% polyester; Body/Sleeve Filler: 90% duckdown , 10% duckfeather
$149.99 Amazon Prime
Sam Edelman Women's, Laguna Boot Black 8 M
Sam Edelman Women's, Laguna Boot Black 8 M
Waterproof leather and stretch fabric upper; Stretch gore panels in the upper for easy on and off with a flexible fit
$169.95 Amazon Prime

3. Blazer and Jeans

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.

Credit: Instagram / morenamiashoes.mx

This is how you can create this look:

MANGOPOP Women's Mock Turtle Neck Long Sleeve Tops Bodysuit Jumpsuit (A Long Sleeve Black, Large)
MANGOPOP Women's Mock Turtle Neck Long Sleeve Tops Bodysuit Jumpsuit (A Long Sleeve Black, Large)
Bodysuits for women featuring mock turtle neck, sleeveless / long sleeve; Tanga bottom, 2 snap buttons butt closure at crotch
$24.98 Amazon Prime
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: Short=28", Medium=30", Long=32"; You may also like Totally Shaping Pull on Bermuda Shorts
$24.99 Amazon Prime
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
$139.95 Amazon Prime
Fossil Women's Kinley Small Crossbody Purse Handbag
Fossil Women's Kinley Small Crossbody Purse Handbag
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.

Credit: Instagram / rosesandrainboots

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
Close-but-comfortable fit with easy movement; Lightweight and soft yarn; Turtleneck neckline
$23.70 Amazon Prime
Floerns Women's Plaid High Waist Bodycon Mini Skirt Black Camel Multi XS
Floerns Women's Plaid High Waist Bodycon Mini Skirt Black Camel Multi XS
Non-stretch material; Occasion: casual/daily/street/office/school uniform, for spring/fall/winter
$24.99
Sale
No nonsense Women's Super Opaque Control-Top Tights, Black/Black, Large
No nonsense Women's Super Opaque Control-Top Tights, Black/Black, Large
90 denier leg for complete coverage; Control top for a smooth, slim look; Stay-in-place waistband fits just below the natural waist
$11.68 Amazon Prime
Sale
Blowfish Malibu Women's Redsen Ankle Boot, Black Local Sheriff, 8.5
Blowfish Malibu Women's Redsen Ankle Boot, Black Local Sheriff, 8.5
Synthetic upper with ruching at vamp; Ankle-high Chelsea bootie shaft with elastic ribbed side goring
$37.23 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

5. Belted Wrap & Leggings

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.

Credit: Instagram / izzyscloset_x

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
$19.99 Amazon Prime

6. Pant Suit with a Wool Trench

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.

Credit: Instagram / fallingfora

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
$92.98
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.
$22.75 Amazon Prime
Sale
ANRABESS Women's Casual Long Sleeve Draped Open Front Knit Pockets Long Cardigan Jackets Sweater 580shenxing-S
ANRABESS Women's Casual Long Sleeve Draped Open Front Knit Pockets Long Cardigan Jackets Sweater 580shenxing-S
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 / Dry clean / Do Not Bleach / Dry Flat / Do not iron.
$49.99 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

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!

Credit: Instagram / angharadbjones

This is how you can create this look:

Sale
Amazon Essentials Women's Classic-Fit Long-Sleeve Button-Down Poplin Shirt, French Blue, Stripe, Small
Amazon Essentials Women's Classic-Fit Long-Sleeve Button-Down Poplin Shirt, French Blue, Stripe, Small
An Amazon brand; Close-but-comfortable fit with easy movement; Soft, durable and cozy tumbled poplin for a lived-in feel right away
$18.10 Amazon Prime
Amazon Essentials Women's Lightweight Long-Sleeve Cable Crewneck Sweater (Available in Plus Size), Charcoal Heather, Medium
Amazon Essentials Women's Lightweight Long-Sleeve Cable Crewneck Sweater (Available in Plus Size), Charcoal Heather, Medium
Close-but-comfortable fit with easy movement; Lightweight and soft yarn; Crew neckline; An Amazon brand
Sale
Kenneth Cole REACTION Women's Salt Chelsea Ankle Boot, Black Leather, 7.5 M US
Kenneth Cole REACTION Women's Salt Chelsea Ankle Boot, Black Leather, 7.5 M US
Pull-on design with goring side panels.; Rounded toe.; Rear pull-tab offers easy entry.; Breathable man-made lining.
$76.98 Amazon Prime

8. Oversized Belted Jacket & Faux Leather Leggings

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.”

Credit: Instagram / franki.dammone

This is how you can create this look:

Sale
Sale
Square Buckle Casual Jean Suede Leather Belt 1 1/2' Wide (Gray, 34)
Square Buckle Casual Jean Suede Leather Belt 1 1/2" Wide (Gray, 34)
Available in 8 different vibrant colors and feels smooth like velvet.; 1.5 inches wide. Comes with 7 belt holes for plenty of room for adjustments.
$17.95
Sale
The Drop Women's Addison Soft Volume Top Handle Bag, Ultramarine Green, One Size
The Drop Women's Addison Soft Volume Top Handle Bag, Ultramarine Green, One Size
Staples by The Drop; 11.75” H x 5.75” L x 3” D; This bag has a 3.5" strap drop; Smooth faux leather
$30.17 Amazon Prime
Sale
CC Classic Winter Fall Trendy Chunky Stretchy Cable Knit Beanie Hat (Solid Sea Green)
CC Classic Winter Fall Trendy Chunky Stretchy Cable Knit Beanie Hat (Solid Sea Green)
Size: One size fits most, unisex, men, women and teen; Head measurement: 56 cm, 22 inches, Size 7 to 59 cm, 23 and 1/4 inches, Size 7 and 3/8
$11.99 Amazon Prime

9. Midi Dress with Cropped Denim Jacket

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.

Credit: Instagram / buenocanada

This is how you can create this look:


10. Oversized Turtleneck and Shacket

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.

Credit: Instagram / lmer_

This is how you can create this look:


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

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.

Credit: Instagram / style_conscience

This is how you can create this look:

Amazon Essentials Women's Long-Sleeve Lightweight Crewneck Sweater (Available in Plus Size), Burgundy, Medium
Amazon Essentials Women's Long-Sleeve Lightweight Crewneck Sweater (Available in Plus Size), Burgundy, Medium
Close-but-comfortable fit with easy movement; Lightweight and soft yarn; Crew neckline; Ribbing at collar, cuffs and hem
Sale
MANGOPOP Women's Basic Faux Suede High Waist A-line Mini Pencil Bodycon Skirt (A Black, Medium)
MANGOPOP Women's Basic Faux Suede High Waist A-line Mini Pencil Bodycon Skirt (A Black, Medium)
Please check our size chart in the last image before ordering.; It is a must-have wardrobe corduroy fall skirt for woman.
$26.98 Amazon Prime
Sale
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
$11.20 Amazon Prime

12. Cropped Puffer and Wide Straight Leg Jeans

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.

Credit: Instagram / saaara57

This is how you can create this look:


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

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.

Credit: Instagram / marissawearsanoutfit

This is how you can create this look:


14. Midi Skirt and Cropped Jacket

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.

Credit: Instagram / blundstoneusa

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
Close-but-comfortable fit with easy movement; Lightweight and soft yarn; Turtleneck neckline
$23.70 Amazon Prime
Sale
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
$7.99 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
$213.19 Amazon Prime

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

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.

Credit: Instagram / michel_nadeau_

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
Available in extended sizes; Premium quality, super stretchy denim; Hugs your curves and keeps its shape all day
$28.99 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
$23.99 Amazon Prime
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
Upgrated Material: Khaki Color; H Line, Long Sleeves, Fully Lined, Belt Cuffs; Dryclean, Do not bleach, Do not tumble dry, Cool iron
$68.99 Amazon Prime
Soda Pilot ~ Women Lug Sole Low Heel Chelsea Fashion Ankle Bootie w/Double Elastic Gore (5.5, GREY NUBUCK, numeric_5_point_5)
Soda Pilot ~ Women Lug Sole Low Heel Chelsea Fashion Ankle Bootie w/Double Elastic Gore (5.5, GREY NUBUCK, numeric_5_point_5)
Shaft measures approximately 5.5" from arch; Platform measures approximately .75"; Latest Fashion and Trend for Stylish and Sexy look
$42.49 Amazon Prime

Are Chelsea Boots In Style 2023?

Almost every style of ankle boot you can imagine is on trend for 2023. 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 Kayla Young

Kayla is the founder of LuxeLuminous. She has worked professionally in the tanning industry for years. She has been interested in esthetics since childhood, and has tried every hair, skin, and makeup product ever produced (more or less).