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10 Chelsea Boot Outfits That Are Effortlessly Cool

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Chelsea boots are a capsule wardrobe staple; here’s 10 ways to wear them.

Boots are a shoe category that can be overwhelming if you’re starting to build your collection from zero. Chelsea boots are a good one to start with. They are short boots, with an elastic shaft, which are flattering for all and look great with oversized silhouettes.

The first Chelsea boot was made in 19th century London, hence the same. Its history is as a horse-riding boot, which explains the clean-cut look, perfect for dressing up an outfit. Combat boots and knee-high boots are more casual or trendy, whereas Chelsea boots will always be a chic, classic look.

If you’re unsure how a Chelsea boot can fit into your style and closet, we’ve put together 10 outfits to style these with.

10 Ways To Wear Chelsea Boots

1. Leggings

Chelsea boots are perfect for pairing with leggings as the shaft fits flush with the ankle. This makes them perfect for pairing with an oversized chunky hoodie or sweater like this.

A great hack for styling a chunky sweater is to wear a structured white shirt underneath to add a level of elegance. Keep the rest of your outfit elevated with a clean-cut bag.

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LULUS Black Vegan Leather Leggings
Lulus

Black Vegan Leather Leggings

At Lulus

Madewell Poplin Oversize Button-Up Shirt
Madewell

Poplin Oversize Button-Up Shirt

At Nordstrom

Ganni Mid Chelsea Boots
Ganni

Mid Chelsea Boots

At Revolve

2. Blazer Dress

For a city-hopping night out where heels might not be appropriate, a pair of flat boots like Chelsea boots is a wonderful option. A blazer dress is great paired with these as the structured silhouette compliments that of the boots.

Cinch in your waist with a fun belt, and keep your jewelry elevated with chunky earrings.

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Bardot Joelle Tuxedo Dress
Bardot

Joelle Tuxedo Dress

At Revolve

Lulus Waylen Black Ankle Boots
Lulus

Waylen Black Ankle Boots

At Lulus

Saint Laurent YSL Cintura Leather Belt
Saint Laurent

YSL Cintura Leather Belt

At Nordstrom

3. Slip Skirt

Slip skirts have been popular in trends over the past few years – and it continues. A jewel-toned slip skirt is the perfect pop of color for an evening outfit, paired with a black sweater and chunky black Chelsea boots.

Accessorize this with a black shoulder bag and a short black coat.

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Show Me Your Mumu Vienna Sweater
Show Me Your Mumu

Vienna Sweater

At Revolve

Madewell Satin Slip Skirt
Madewell

Satin Slip Skirt

At Nordstrom

Dune London Picture Platform Chelsea Boots
Dune London

Picture Platform Chelsea Boots

At Nordstrom

4. Shearling Coat

The hottest style of outerwear right now is this short shearling oversized coat. The oversized silhouette means it pairs well with a sharp Chelsea boot with tights and a mini skirt or dress.

Keep the rest of your outfit simple with a tote bag and chunky jewelry in your favorite metallic tone.

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HiSO Dez Reversible Shearling & Suede Jacket
HiSO

Reversible Shearling & Suede Jacket

At Nordstrom

AGOLDE Recycled Leather Liv Mini Skirt
AGOLDE

Recycled Leather Liv Mini Skirt

At Revolve

 Dr Marterns. 2976 Chelsea Boots
Dr Martens.

2976 Chelsea Boots

At Nordstrom

5. Wool Coat

A sharp, oversized wool coat is another big trend in winter fashions. If you want to experiment with a non-black Chelsea boot, try coordinating it with another aspect of your outfit, such as with your sweater or handbag.

For the winter sun, keep a pair of sunglasses either in your coat pocket or in your handbag to avoid squinting while you take an afternoon stroll.

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Rag & Bone Thea Italian Wool Coat
Rag & Bone

Thea Italian Wool Coat

At Revolve

Nordstrom Mia Chelsea Lug Boots
Nordstrom

Mia Chelsea Lug Boot

At Nordstrom

Le Specs Work It Sunglasses
Le Specs

Work It Sunglasses

At Revolve

6. Skinny Jeans

A great way to style Chelsea boots for the winter is with skinny jeans. If you’re taking a European vacation at the start of the year, it can be chilly, and boots should be a packing staple.

A chic way to wear these is with a sweater, or thermal, and with an oversized wool blazer as a coat. A crossbody bag can actually help create some structure in the outfit by showing some shape.

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Sam Edelman Braelynn Relaxed Double Breasted Blazer
Sam Edelman

Relaxed Double Breasted Blazer

At Nordstrom

Lulus Vegan Leather Skinny Jeans
Lulus

Vegan Leather Skinny Jeans

At Lulus

ALLSAINTS Amber Boots
ALLSAINTS

Amber Boots

At Revolve

7. Maxi Coat

If you have a statement coat to wear, either with many colors or fur patches like these, Chelsea boots can tone it down for everyday wear.

Keep the rest of your outfit in a neutral tone, like black or grey, so as not to overpower the rest of your look.

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Simon Miller Bruer Coat
Simon Miller

Bruer Coat

At Revolve

Lulus Tea Reader Black Sweater Dress
Lulus

Tea Reader Black Sweater Dress

At Lulus

Prada Chocolate Chelsea Boots
Prada

Chocolate Chelsea Boots

At Nordstrom

8. Maxi Dress

Thanks to SKIMS, neutral maxi dresses are a staple in every closet. Regardless of the color, Chelsea boots are a great way to add structure to this garment which can sometimes look too casual.

A small shoulder bag and slicked bag hair make this the perfect “model off duty” look.

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SKIMS Long Sleeve Crewneck Dress
SKIMS

Long Sleeve Crewneck Dress

At Nordstrom

Dolce Vita Hoven H2O Booties
Dolce Vita

Hoven H2O Booties

At Revolve

Lulus Black Faux Leather Shoulder Bag
Lulus

Black Faux Leather Shoulder Bag

At Lulus

9. Cardigan

Cardigans are underrated in mainstream fashion, but French model all have them as part of their capsule closets. Focus on a neutral color that you like, whether grey, cream, or another tone, and ensure it is in a natural fabric like cashmere or wool.

Keep the rest of your outfit fitted – jeans and a fine knit sweater make perfect accompaniments.

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Lovers and Friends Katherine Long Cardigan
Lovers and Friends

Katherine Long Cardigan

At Revolve

Lulus Nude Platform Ankle Boots
Lulus

Nude Platform Ankle Boots

At Lulus

Saint Laurent Le 5 à 7 Leather Hobo
Saint Laurent

Le 5 à 7 Leather Hobo

At Nordstrom

10. Monochrome Outfit

Another fabulous way to style black Chelsea boots is with a monochrome outfit. A black outfit always looks chic, and means you don’t need to worry about coordinating your pieces.

If you have a statement monogram or colorful handbag you’re looking to style, this is the perfect moment to use it.

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MANGO Belted Wool Blend Coat
MANGO

Belted Wool Blend Coat

At Nordstrom

525 Kylie Rib Midi Dress
525

Kylie Rib Midi Dress

At Revolve

Sandro Leather Chelsea Boots
Sandro Paris

Leather Chelsea Boots

At Harrods

We hope you’ve enjoyed this guide on how to wear Chelsea boots for women, as well as the 9 chic outfit ideas that we shared!

Up next: 15 Best Shoes To Wear With A Jumpsuit (Chic Or Casual)

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