Chelsea Boot Style Guide for Women

Thalita Ferraz // Last Update: January 3, 2023 // 0 Comments

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Are you familiar with Chelsea boots? Even if you aren’t familiar with the name, I’m sure you’ve seen them worn before. They’re quite popular footwear, especially during cooler weather.

Chelsea boots are ankle high boots, sometimes with or without small heels, that have an elastic siding at both the inside and outside of the ankle. They often will have pull tabs on them too to aid in putting them on.

I overheard a conversation about them at one point, and the girls were discussing that they weren’t sure how to wear the Chelsea boots. 

Mostly they weren’t sure if they were supposed to tuck their pants into the boot (even though it’s an ankle boot) or if their pants were supposed to cover them since they have the pull tab. 

In case you’ve ever wondered the same thing, I wanted to show you how you can style Chelsea boots without confusion!

In this style guide, we’ll be focused solely on discussing Chelsea boots.

Best Levi’s to Wear With Chelsea Boots

Levi’s are a fashion classic that is loved by all. It’s understandable, they last forever, come in so many styles, are made for all ages, and for both men and women. But of course, we’re only talking about us ladies looking fab on Hello Thalita. 

I wanted to show you a few specific ways you can style your Levi’s with your Chelsea boots!

Levi Wedgie Jeans & Chelsea Boots

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These Levi Wedgie jeans like pictured here are one of their most popular fits right now. They’re designed to be super flattering, better than the classic 501’s, and vintage inspired while hugging your hips and waist! 

So of course, especially with the straight leg and raw hem, they look great with these Chelsea boots.  Wait, did you see these Chelsea boots? They’re snake print! Hello gorgeous! Anyway, the raw hem means you don’t need to do anything to the bottom of these pants! Let them be.

Repurposed Levi 501’s & Chelsea Boots

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These are actually repurposed Levi 501’s! Aren’t they cute? They’re called Leandra High Rise Crop Flare Levi’s, but any flared pair of Levi’s will give you a similar look!

It’s super cute, especially since her Chelsea boots match her jacket. The important thing though, are the Levi’s of course.

Chelsea Boots with Scrunched Socks

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A cute way to wear socks with Chelsea boots is with cuffed up ankles! Having scrunched down socks with Chelsea boots and cuffed pant legs gives this great little… break between the sock and pant leg. It gives the look an extra dimension and some depth. It’s a great way to style socks with them!

Chelsea Boots and a Midi Skirt

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You are allowed to wear Chelsea boots without some form of legwear. Take this outfit for example, she’s wearing hers with a black midi skirt, gray sweater, and an awesome panama hat. It’s super edgy and she’s able to show some leg while rocking her Chelsea boots.

This also means that you can wear your Chelsea boots with skirts and dresses, too!

Best Jeans to Wear With Chelsea Boots

Let’s talk about all the different types of jeans you can wear with Chelsea boots. Specifically, we’re going to look at more popular cuts like cropped jeans, skinny jeans, and even flared jeans!

Don’t forget that you can wear jeans of different color, wash, and styles. Boyfriend jeans also look really great with Chelsea boots, but I’ll let you look into that one.

Remember, that you want your Chelsea boots to be seen! So your jeans selection shouldn’t go all the way to the ground or cover the boots much (if at all).

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These black slightly distressed cropped jeans are looking great with these black Chelsea boots! I like the look that cropped jeans have with Chelsea boots because you don’t need to cuff the ankles at all to show the boots plus a little skin. 

Showing that little bit of skin helps break up color, especially if your pants and boots are the same, and it helps elongate the look of the leg a little bit.

Chelsea Boots with Checkered Pants

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Don’t forget patterned pants! They deserve to be taken out on the town! This is a cute almost unruly outfit with checkered pants, an untucked button up, a leather jacket, with Chelsea boots and a beanie! Super cute, right?

Best Socks to Wear With Chelsea Boots

Wearing socks with Chelsea boots is a great way to add a little extra oomph to your outfit. Socks are like fair game when it comes to fashion. You can add them to your look and they can be as fun and wild as you allow them to be. 

Then of course, they give your look this comfortable cozy look, which makes them a super valuable accessory during the fall and winter. Yep, I said accessory. Let’s talk about accessorizing with socks!

Chelsea Boots and Hiker Socks

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These socks and boots here are rustic almost. She’s channeling a little bit of hiker sock inspiration and I’m about it! Just wearing them over top of her jeans and have them scrunched down.

Cute Outfits With Chelsea Boots

Chelsea boots don’t only have to be worn with jeans, though. They’re great with leggings, tights, dresses, skirts, overalls, leather pants, joggers, you name it! 

I wanted to show you how you can style them with a mini skirt, a midi skirt, and with patterned pants!

Chelsea Boots with a Mini Skirt

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There are other ways to wear Chelsea boots (besides with jeans) and be cute! This is a cute way to wear a mini skirt with Chelsea boots! She’s rocking a chunky sweater, gray mini skirt, black tights, and black boots. 

I’m all about these tights! We can expect tights with patterns on them to be popular this fall too, so maybe keep this outfit in mind for inspiration later!

Best Jeans to Wear With Chelsea Boots

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Retro will never truly go out of style. Check out these high waist retro flared jeans! She’s tucked a basic tee into the top and is displaying her boots beneath the flare jeans but was careful to not cover them with her pant leg. This is important!

Yes, you could technically wear them and cover them completely, BUT they’re meant to be displayed. This is a great way to do that while wearing something other than skinny or straight leg jeans.

Loosely Rolled Levi Pant Legs & Chelsea Boots

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Here’s another cute way to wear your straight leg or boot cut Levi’s with your Chelsea boots. Rather than cuffing the bottom of the pant leg, you loosely roll them up giving them a similar yet unruly feel.

What is important here is that the boots aren’t covered! Plus these light wash jeans are awesome.

Best Way to Wear Jeans With Chelsea Boots

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It’s important to show your Chelsea boots off. So if you’re going to wear them, one of the best ways to do that is by cuffing the ankle up some so it shows the boot and some leg. The cuff draws the eye down and gives those awesome boots some attention! They deserve it.

Best Way to Wear Jeans With Chelsea Boots

Sounds simple, doesn’t it? The best way to wear jeans with Chelsea boots… well, realistically, how many ways can you wear jeans? 

The thing is that Chelsea boots want to be seen. So the best way to wear jeans with your Chelsea boots involves letting that happen! You’re about to see cuffed jeans, jeans tucked into socks, and jeans just slightly over the top of the boots.

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Another way you can wear your jeans with your Chelsea boots is by tucking them into a pair of long/ chunky socks. Not only is it functional, but having the socks there sort of does what cuffing the bottoms do- draws the eye down and makes the boots noticeable!

Best Way to Wear Jeans With Chelsea Boots

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If you’re not wanting to wear cropped jeans or cuff your pants to show your ankles, and you’re not wanting to wear chunky socks with them, you can absolutely just wear straight leg or skinny jeans with them and let them be either tucked into the boot or just over the top. Totally okay!

Best Jeans to Wear With Chelsea Boots

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Here’s a cute brown turtleneck sweater with black skinny jeans and Chelsea boots. You can see here that her skinny jeans aren’t tucked into her boots, they aren’t cuffed, and they leave just a little bit of leg showing down there similar to the cropped pants above.

Skinny jeans can go all the way down into the boot, however you benefit from allowing some skin to show just like I mentioned above.

Best Socks to Wear With Chelsea Boots

Wearing socks with Chelsea boots is a great way to add a little extra oomph to your outfit. Socks are like fair game when it comes to fashion. You can add them to your look and they can be as fun and wild as you allow them to be. 

Then of course, they give your look this comfortable cozy look, which makes them a super valuable accessory during the fall and winter. Yep, I said accessory. Let’s talk about accessorizing with socks!

Chelsea Boots and Patterned Socks

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If you’re going to show off some socks, it’s a great opportunity to wear cute ones! So these Chelsea boots are showing off cute winter gray patterned socks. Like the ones above, they’re pulled up over her pant legs. Keeping those ankles warm!

So, now that we’ve gone over the best jeans to wear with Chelsea boots, the best ways to wear jeans with them, the best Levi’s to wear with them, other cute outfits that include Chelsea boots, and how to wear socks with Chelsea boots I’m dying to know: What was your favorite look? 

I personally love the midi skirt outfit with the Chelsea boots. The whole outfit is just so cute! But I want to hear from you! How do you wear your jeans with your Chelsea boots? Do you ever wear them with dresses, skirts, or leggings? Tell me in the comments below!


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