How to Wear Chelsea Boots – 14 Outfits & 11 Boot Options

If you’re looking for a boot that can be worn in just about any way, with just about any outfit, look no further than Chelsea boots! Not only are Chelsea boots timeless, they’re incredibly comfortable and so versatile.

If you’re unfamiliar with them, here’s what you need to know. Chelsea boots are close fitting, ankle high boots with an elastic side panel to easily pull them on and take them off. Most have pull tabs in the back of the boot (some also have them in the front) to help you get them on even easier.

Here’s a fun fact for you – they’ve been around since the Victorian era when Queen Victoria’s shoemaker Joseph Sparkes Hall created them for the queen to do her daily walks in. If they’re great option for a queen, I’m thinking they’re a great option enough for me and you! ūüėČ

They grew in popularity in the 1950s and 60s in the UK. They’re were associated with King’s Road (a street in Chelsea) which is how they got their name. Everyone from the Beatles to the Rolling Stones to model Jean Shrimpton were wearing them!

The most popular color are black Chelsea boots but the come in a ton of different colors You’ll see brown Chelsea boots, white Chelsea boots, even deep green one!

If you want a pair of Chelsea boots and are stumped on how to wear them or just need a refresh on ideas with how to style yours, I’m here for you! Today I’m going to share a variety of different outfits wearing black classic Chelsea boots to help inspire your next outfit.

14 Ways to Wear Chelsea Boots

how to wear chelsea boots

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From casual outfits to dressier outfits, here’s some fun new ways to wear your Chelsea boots.

1. All Black : Black Leggings and a Black Sweater

chelsea boots and all black outfit

When in doubt, go black! One of the most classic and easy ways to wear Chelsea boots is black on black on black! I love this simple look of leggings and an oversized sweater! It’s easy to wear and you’ll always look chic!

Love leggings? Here’s more faux leather leggings outfits!

Shop this outfit: Sweater | Leggings | Socks (similar here) | Boots

2. Black Leggings and an Oversized Sweater

chelsea boots and sweater and leggings

Have an oversized sweater you love? Throw it on with leggings and your Chelsea boots! If you like a little bit of extra length, add a longer tee or tank underneath (this Free People Long Sleeve is my fav).

Cozy socks pulled over your leggings give this an extra cozy vibe!

Shop this outfit: Sweater | Leggings | Socks (similar here) | Boots

3. Leggings and a Shacket

chelsea boots and shacket

Love an oversized shacket? Leggings and a shacket are the perfect combo for fall and winter. Add in cozy socks pulled slightly over your leggings to complete the look!

Want more shacket fun? Head to this post all about shackets.

Shop this outfit: Long Sleeve | Shacket | Leggings | Socks (similar here) | Boots

4. Leggings and a Sherpa Sweatshirt

chelsea boots and leggings

When the temperatures start to drop in the colder months, chances are you’ll be reaching for things a bit more cozy and comfy. This sherpa style hooded sweatshirt softens up the tough looking vibe of the Chelsea boot.

This outfit is perfect for running errands or a walk around the neighborhood!

Shop this outfit: Fleece Sweatshirt | Leggings | Socks (similar here) | Boots

5. Midi Skirt and Bodysuit

chelsea boots and black skirt

Yes, your Chelsea boots can be worn to the office! This outfit proves that! Keep things sophisticated and professional by pulling on a neutral colored midi skirt over a black bodysuit.

If you’ve never tried a bodysuit under a skirt you are missing out! They give you a completely seamless look. No shirts coming untucked in the middle of a meeting or looking sloppy – they’re magic!

Pull on your ankle boots over fun sheer socks, low socks or even higher cozy socks. This is a great way to look professional yet chic at the same time.

Shop this outfit: Bodysuit | Skirt | Boots

6. Midi Skirt and Graphic Tee

chelsea boots and black skirt

Heading out for drinks after work? I’ve got you. Swap the sleek bodysuit for a fun graphic tee! A super easy way to make a midi skirt less professional and more fun is to simply swap a neutral top for a more fun top like this graphic tee.

You can even pull the midi skirt up a bit on your waist to reveal a bit more of your black boots and those fun leather soles and your ready for happy hour!

Shop this outfit: Graphic Tee (code PANDS for a discount!) | Skirt | Boots

7. Midi Skirt and Henley

chelsea boots and midi skirt

I love a good pleated maxi skirt and this green one is no different! The metallic vibe of it pairs nicely with the leather boots and the casual look of the Henley is great for heading to coffee or running errands!

Shop this outfit: Henley | Skirt | Boots

8. Midi Skirt and Black Bodysuit

chelsea boots and midi skirt

Take that pleated maxi and dress it up a bit! I’m again wearing the same bodysuit from the previous outfit and it completely changes the look and feel of this outfit. A fitted seamless top gives this top a look that perfect for business meetings or dinner out!

Shop this outfit: Bodysuit | Skirt | Boots

9. Sweater Dress

chelsea boots and sweater dress

I love sweater dress (I even have a whole post with ideas on how to wear them) and they look so fun with your black leather boots! Pull on a pair of textured or patterned black tights for those extra cold days.

Shop this outfit: Sweater Dress | Boots

10. Maxi Skirt and Black Bodysuit

chelsea boots and maxi skirt

This maxi skirt may be my favorite skirt for year round wear! During cooler months, you can easily pull off this skirt by pairing it with a slim cut black shirt (again, like this bodysuit) and your Chelsea boots.

This is also a great option if you needed more of a dress shoe since just a bit of your boot will be peeking out from under the skirt!

Shop this outfit: Bodysuit | Skirt | Boots

11. Black Jeans and White Cardigan

chelsea boots, jeans and cardigan

One of the simplest and most classic way to wear your black leather Chelsea boots is with black jeans! This white button down cardigan goes with just about everything and I love it paired with a pair of skinny jeans and a pair of boots!

Depending on your own personal style, you can fold your jeans up so they hit right at the top of the boots or add a pair of cozy socks and pull them up over your pants!

Shop this outfit: Cardigan Sweater | Pants | Boots

12. Black Skinny Jeans and a Blazer

chelsea boots, skinny jeans and blazer

Blazers are a modern look that’s back in full force. Pair it with a graphic tee like me for date night or drinks with girlfriends or swap the graphic tee for a simple white t-shirt for a cool casual look.

Need to go to the office and can’t wear jeans? Simply swap the jeans for work pants and away you go!

Shop this outfit: Blazer (sold out, similar here and here) | Graphic Tee | Pants | Boots

13. Cropped Jeans and a Denim Jacket

chelsea boots, cropped jeans and denim jacket

Want an every more on trend look? Swap the skinnies for cropped straight leg jeans! These cropped jeans look fantastic with a printed denim jacket with a simple white t-shirt under it.

Shop this outfit: Denim Jacket | White Tee | Pants | Boots

14. Jeans and a Sweatshirt

chelsea boots, cropped jeans and sweatshirt

For everyday wear, throw on a sweatshirt with your copped jeans! This relaxed appearance still looks effortlessly chic with the perfect pair of Chelsea boots and cropped blue jeans.

Shop this outfit: Sweatshirt | Jeans | Boots

If you still don’t own a pair of Chelsea Boots, here’s a few to check out!

11 Amazing Chelsea Boots

chelsea boots
  1. Sam Edelman Women’s Laguna Chelsea Boot (these are the ones I own! Size up a half size.)
  2. The White Version! Sam Edelman Women’s Laguna Chelsea Boot (I love them so much I need them in white!)
  3. Steve Madden Hayle Platform Chelsea Boot
  4. Dr. Martens Chelsea Boot
  5. Dolce Vita Haddie Wedge Chelsea Boot
  6. Steve Madden Women’s Howler Fashion Boot
  7. Blundstone Women’s Blundstone 558 Black Boot
  8. UGG Women’s Harrison Chelsea Fashion Boot
  9. Lisa Vicky Chelsea Boot
  10. Timberland Courmayeur Valley Chelsea Boot
  11. Sorel Emelie II Waterproof Chelsea Boot

I hope this post gives you the confidence to try out your Chelsea boots in a new way or inspires you to purchase your first pair of Chelsea boots!

I waited so long to get my first pair and have worn them non-stop ever since they arrived on my front step.

If you want even more outfit inspiration, check out one of these posts!

About Jen

Jen is a mom of 3 who loves frozen cookie dough, plants and a generous pour of creamer in her coffee. Her biggest joy is helping others find joy in their life, style and home through tips, tutorials and encouragement. She also runs 2 additional blogs. Feel free to send Jen a message or join the fun on Instagram!

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