How To Wear Chelsea Boots: 9 Chic Outfit Ideas For Women

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We all know about combat boots, ankle boots, and the iconic knee-highs, but have you ever considered adding a pair of Chelsea boots to your wardrobe? If so, check out our guide on how to wear Chelsea boots for women.

You know you’re a “cool girl” when you wear Chelsea boots. Something about the cut, style, and shape of these boots makes them so incredibly versatile and adds a level of edginess to any woman’s outfit.

From the classic Chelsea boots to unique snakeskin print, there are endless ways to rock this shoe – whether you’re going for a casual outfit, a sophisticated look, or something a little bit grungier.

Chelsea boots are named after the Chelsea neighborhood in London, UK. They were originally made for women who cleaned up around the stables at the Royal Mews, but they became popular with upper-class ladies as well.

Design-wise, these boots are a mid-calf boot that has a rounded toe and a chunky sole made of rubber. The boot is usually made of leather (or close to it), but it can also be made of suede or fabric. It has an elastic side panel with pull tabs on the back of the boot.

This versatile shoe style can be worn with just about anything, from jeans to dresses for a fashionable look. If you want to incorporate this trend into your wardrobe, scroll down to see some chic outfit ideas. We hope these photos will help you find your own way of styling these comfortable boots!

How To Wear Chelsea Boots For Women

1. Cozy Knits & Sweaters

Cable knit cream sweater
Get this sweater on Lane201

Sweaters are a simple base layer that can be used to dress your outfit up or down, especially for the colder months. It also has the benefit of adding texture and warmth to your outfit with its softness.

Adding an oversized sweater over your Chelsea boots can give you a relaxed look that’s very on trend right now, especially if you opt for a nude pair of Chelsea boots with a cream-colored sweater! You can wear these with an everyday pair of skinny blue jeans, or for a more fashion-forward look, pair this combo with a white tennis skirt instead.

2. Plaid Shirts

A plaid shirt with a comfortable pair of Chelsea boots is a classic combo for a reason – they are both fall and winter staples. The plaid shirt can be worn with any color of boot, really. It’s all about playing with different textures and colors to make it look fun and modern!

We love a classic pair of black Chelsea boots for a cool casual look. For a more unique style, go for brown or burgundy Chelsea boots instead for a grounded look that’s perfect for everyday wear.

3. Feminine Dresses

White puff sleeve shift dress
Get this dress on Impressions

If you have a nice shift dress that’s short or above the knee, it will look great with Chelsea boots for a chic, feminine look.

The best part about wearing Chelsea boots with a dress is that they can make any outfit feel more put-together! You can always add accessories like necklaces or hats to bring out your personal style even further.

For a dress that’s more winter-appropriate, go for a nice, warm sweater dress instead, and pair it with white or cream Chelsea boots!

4. Mini Skirts

You can rock Chelsea boots with shorter skirts and an oversized jacket for an on-point, fashion-forward outfit, but you can also play around with different tops like sweaters, off-the-shoulder blouses, bodysuits, tanks, and more.

If you have a belt that matches your shoes, consider styling your outfit with it in order to create an even hemline for that perfect hourglass silhouette. Top it all off with a designer crossbody bag, and you’re all ready to hit downtown!

5. Leggings

How To Wear Chelsea Boots For Women: Black leather leggings and teddy coat
Get these leather leggings on Pretty Little Thing

Black leggings are another great way to wear Chelsea boots for women, especially in the fall and winter months. If you’re a fan of faux leather leggings, consider trying them out with your Chelsea boots for a cool, uniform look!

They can be quite edgy and an easy way to create a stylish look, plus they can make you feel warm and cozy in the cold weather compared to basic leggings.

If you want to play around with textures, you can also opt for a pair of suede Chelsea boots instead.

6. Shirt Dresses

White shirt dress
Get this shirt dress on Princess Polly

A shirt dress is the perfect choice when you want to stay warm, but don’t want to feel too bulky. This basic silhouette can be dressed up or down with a variety of accessories, from a blazer, to a sweater vest and heels to boots. Chelsea boots work well here because they’re tall enough that your outfit stays feminine without looking frumpy.

You can wear a shirt dress as it is, or add a sweater vest over it – this look has been particularly very trendy these days.

7. Long Dress + Leather Jacket

Beige ribbed tank dress
Get this dress on Pink Lily

This is another great outfit idea for the winter season. It’s a little bit more casual but it still looks super chic and stylish. You can wear this with your leather jacket or even your long trench coat if you want to keep warm.

For this look, we recommend wearing a long ribbed tank dress with black boots and a leather or denim jacket of your choice as shown in the photo above.

It’s a cute and sophisticated look that’s great when you’re planning to grab lunch with friends, followed by a shopping spree right after.

8. Ankle-Length (Or Skinny) Jeans

Denim jeans
Get these jeans on Pink Lily

Jeans are another go-to for women, since they’re such a classic wardrobe piece that everyone already owns. When you wear jeans with your boots, they can be dressed up or down depending on the rest of your outfit. You can wear them with long sweaters and t-shirts, as well as dressy blouses or simple tank tops.

For the best look, we recommend sticking with trusty skinny jeans or opting for ankle-length jeans that create a clear divide between the boots and the jeans. If you don’t own a pair of cropped jeans, simply cuff your jeans above the ankle, so that they won’t get into the way of your boots.

Otherwise, the bottom half of your outfit could end up looking quite bulky!

9. Oversized Blazers

How to wear Chelsea boots for women: with oversized blazers
Get these boots on Princess Polly
Oversized leather blazer
Get this blazer on Princess Polly

Is there anything that doesn’t look good with an oversized blazer? We think not. Chelsea boots are no exception to this rule, and they’ll pair nicely with any complementing colored blazer, from neutrals to khaki green, black and even bright pastels in the springtime (we recommend cream or white Chelsea boots with pastels!).

A good place to shop for oversized jackets or blazers is ASOS or Princess Polly — they have great options that won’t break the bank. Look for ones with interesting details on them like multiple pockets or button closures.


The Chelsea boot is a versatile shoe style that can be worn with just about any outfit. This is one of the reasons why it’s such a popular style choice among fashionistas and celebrities.

It goes well with dresses, skirts, jeans, leggings, and shorts — you’ll find yourself reaching for them all season long! The ideas that we’ve shared with you are just the beginning – there are so many other outfits that you can re-create with Chelsea boots, so make the most of your already existing wardrobe and see which pieces you can throw together!

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! If you’re still looking for more fashion inspiration, check the posts down below.

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