• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer
Cleo Madison
  • Style
    • Women’s Fashion
    • Disney Outfits
    • Modest Fashion
    • Accessories
  • Lifestyle
    • Holiday
    • Travel
  • Beauty
  • Motherhood

9 Chelsea Boot Outfits That’ll Surely Make A Statement

Published by Liz Morgan

Disclosure: Some of the links below are affiliate links. At no cost to you, I will earn a commission if you click through and make a purchase. 

Chelsea boots are cute year round, but especially in the fall and winter. If you’re wanting to wear Chelsea boots, but are struggling with what to wear with them, then take a look at these Chelsea boot outfits for women.

If you’re wondering what a Chelsea boot is, it’s an ankle boot that is slim and fitted with a side panel of elastic.

They typically have a tab or loop in the back to help you get them on and some have another tab in the front to help even more.

Chelsea boots come in a lot of different colors, but the most common color is black. Other colors you’ll see frequently are tan, white, and sometimes brown.

There are different heights for how tall the anklet boots are and the soles can be different heights too. Some are chunky, platform style, lug soles, and others are more flat.

You can wear them casually or put together a dressy outfit. You can wear them to work, school, date night, or really anywhere.

It’s a great shoe that is very trendy, stylish, and fashionable. Adding Chelsea boots to your outfit is a quick way to instantly look more put together.

You’re going to love these Chelsea boots outfit ideas!

#1 Chelsea Boot Outfit – With A Skirt

styling chelsea boots with skirt

image credit

Chelsea boots are super cute with a skirt. You can wear them with knee length skirts or midi skirts. Maxi skirts are a little long for them since they would cover a lot of your boots.

This outfit is black Chelsea boots with socks that barely show, a light wash knee length denim skirt, and a tan sweater that buttons up. I love chunky boots for Chelsea boots outfits.

Shop this look:

  • Similar Chelsea boots here
  • Similar sweater here
  • Similar skirt here
  • Socks here

2. With A Cardigan

chelsea boot outfit with cardigan

image credit

This is one of the cutest Chelsea boots outfits for fall! She is wearing black Chelsea boots that are a little taller, a long tan cardigan, distressed mom jeans that are rolled up a little, and a white tee.

Shop this look:

  • Similar boots here
  • Similar jeans here
  • Similar sweater here
  • Similar shirt here
  • Similar purse here

Related Content: How To Style Booties

3. With A Sherpa

outfit featuring sherpa and brown chelsea boots

image credit: fashionjackson

Sherpas are so cozy and fashionable. I love this tan Chelsea boots outfit. She’s wearing a white sherpa jacket, light brown Chelsea boots, black faux leather leggings, and a black shirt.

Shop this look:

  • Similar boots here
  • Similar sherpa jacket here
  • Leggings here
  • Similar shirt here

4. With An Aviator Jacket

styling chelsea boots with an aviator jacket

image credit

This outfit is a black women’s aviator jacket with black chunky Chelsea boots, tan pants, and a white sweater. This outfit is so fashionable and has a really fun vibe to it.

Shop this look:

  • Similar chunky boots here
  • Similar aviator jacket here
  • Similar pants here

5. With A Sweater

chelsea boots outfit with sweater

image credit

Sweaters are classic for fall and they look great with Chelsea boots! This outfit is a tan turtleneck sweater with black boots, and black skinny jeans.

Shop this look:

  • Similar boots here
  • Similar sweater here
  • Similar pants here

6. With An Oversized Sweatshirt

styling white chelsea boots with an oversized sweatshirt

image credit

Pairing an oversized sweatshirt and Chelsea boots gives you the ultimate cozy look for running errands. She’s wearing white Chelsea boots with a white oversized pullover sweatshirt, and black faux leather leggings.

This is one of my favorite Chelsea boot outfits!

Shop this look:

  • Similar boots here
  • Leggings here
  • Similar sweatshirt here

7. With Black Jeans

styling black chelsea boots with black jeans

image credit

Black jeans look so good with Chelsea boots, especially straight leg jeans and mom jeans. This outfit is black leather Chelsea boots with black straight leg cropped jeans, a white t-shirt, and an olive green utility jacket.

Shop this look:

  • Similar boots here
  • Similar jeans here
  • Similar utility jacket here
  • Similar tee here

8. With Faux Leather Leggings

styling chelsea boots with faux leather leggings

image credit

Faux leather leggings look amazing and so sleek with Chelsea boots. I love the look of the leggings being tucked into the boots.

This outfit has tan Chelsea boots, black faux leather leggings, a white sherpa jacket, and a white shirt. This outfit is casual and super cute for running errands or going to lunch with friends.

Shop this look:

  • Similar boots here
  • Leggings here
  • Similar sherpa jacket here
  • Similar tee here
  • Crossbody bag here

9. With A Dress

chelsea boot outfit with striped dress

image credit

Any Chelsea boots should work with a dress, but these lug sole ones look so cute and dressy.

This outfit is black Chelsea boots with a stripes dress and a rust cardigan.

Shop this look:

  • Chelsea boots here
  • Similar dress here
  • Similar cardigan here

You can pair them with so many other pieces too, like a denim jacket, a graphic tee, or a sweater dress.

Pin this image so you can find this post later!

chelsea boots outfits

As an Amazon Associate I earn from qualifying purchases.

Filed Under: Women's Fashion

Subscribe

to get blog updates.

Previous Post: « 4 Tips For Building A School Capsule Wardrobe That’s Cute And Comfy
Next Post: Say Goodbye To Pilling In Your Leggings »

Primary Sidebar

Welcome

Elizabeth Morgan who owns Cleo Madison

I'm Liz, a mama of four living in Utah. Here you'll find posts about fashion, motherhood, travel, and more!

Join The Newsletter

Get notified of new posts and receive a FREE eBook with all of my best modest fashion hacks!

Follow Along

  • Facebook
  • Instagram
  • Pinterest
  • TikTok
  • YouTube

Footer

COPYRIGHT © 2025 CLEO MADISON

About • Contact • Privacy Policy • Accessibility • Terms & Conditions