6 Ways to Wear Black Chelsea Boots
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  • Writer's pictureBrenda

6 Ways to Wear Black Chelsea Boots

Updated: Sep 21

Chelsea boots have become what is arguably the most popular type of Fall boot. If you run a Google search for the words ‘Fall boots,’ you’re more than likely to stumble across a range of Chelsea boots.

What makes Chelsea boots so popular is their sleek semi-formal design along with their ease of wear. In terms of ankle boots, they are definitely number one and can be paired with everything from jeans to skirts and dresses.


In today’s blog post, we would be covering different ways you can style not just a black pair of Chelsea boots but brown Chelsea boots as well. Fist things first, let’s determine what exactly a Chelsea boot is in case you may have heard the name before but are unsure what this classic style of boot looks like.

What is a Chelsea boot?

As per Wikipedia: Chelsea boots are close-fitting, ankle-high boots with an elastic side panel. They often have a loop or tab of fabric on the back of the boot, enabling the boot to be pulled on. The boot dates back to the Victorian era, when it was worn by both men and women. Queen Victoria’s shoemaker, Joseph Sparkes Hall can be thanked for this iconic invention.

At the time, the boot was popular among horse back riders and would also be use as a walking boot – I mean if the Queen herself was wearing it, it had to be good, right?

The easiest way to spot a Chelsea boot is the elastic side panel. This makes them easier to slip on as Chelsea boots tend to not have any zippers.

Get the look HERE

How do you wear Chelsea boots?

Well, we’re about to answer this question in-depth but know that a pair of chelsea boots can be dressed up or down to create more formal outfits as well as casual outfits. They can be styled with a midi skirt, a pair of jeans or pants during the Fall and also paired with dresses and shorter skirts during the warmer months.

I would be covering the different outfits you can create with a pair of these boots so keep reading if you’re looking for some great outfit inspiration.

Before we talk about the chic outfits you can create with a pair of Chelsea boots, I would like to share some great sites where you can find the perfect pair of brown or black Chelsea boots, depending on your preference.

Disclosure: This post may contain affiliate links, which means that I get a commission if you decide to make a purchase through our links, at no cost to you.

i) Banana Republic has the perfect brown suede Chelsea boots. I love the rich dark brown color as well as the great traction seen on the rubber sole. The lining is comprised of lambskin leather which means this pair of boots would be warm and comfortable. These boots would great with a pair of dark wash jeans or leggings and a sweater.

ii) DSW brings us a range of Chelsea boots from different brands. Some of them feature a higher platform heel while others are true to the classic Chelsea look. Dr. Martens have quickly become the go-to brand when it comes to Chelsea boots. Based on the thousands of 5 star reviews, these boots are comfortable, easy to wear (thanks to the dual elastic side panels) and also stylish.

These leather chelsea boots are meant to be worn everyday and were designed with that in mind. If you’re looking for warmer Chelsea boots, Doc Martens also offers a similar Chelsea boot with faux-fur lining which can be found HERE. If you are going to invest in a pair of black Chelsea boots, a pair of Dr. Martens should be your first choice.

iii) Steve Madden offers a more affordable Chelsea boot if you’re working with a tighter budget. If you’re looking to stray away from black boots, these ones come in both tan and chestnut colors as well. With their stacked soles, these boots would give you a little height without the discomfort of a stiletto heel. They would look great paired with black leather leggings or black tights and a flannel shirt.

iv) If you’re looking for a very casual Chelsea boot you can wear when it’s warmer outside, ECCO has this great pair of Soft 7 Chelsea boots in a variety of different colors. It almost looks like a high top sneaker and would be a great option to go with when a proper Chelsea boot may be a bit too warm for the weather.

I own a few pairs of ECCO Soft 7 sneakers and can tell you first hand they are the most comfortable sneakers you can own.

Now that I’ve shared my favorite Chelsea boots, let’s dive into the various Chelsea boots outfits you can try this Fall/Winter.

1) Chelsea boots and a midi skirt

Chelsea boots work great with a midi skirt and can be worn with one during the Fall or Summer. During the cold weather, pair the boots with a sweater and midi skirt to create a look appropriate for the office or an out-of-office meeting. When it’s warmer, you can swap the sweater for a blouse or simple top. Feel free to tuck in your top for a more formal look.

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2) Chelsea boots and skinny jeans

I’ve said it many times on this blog that skinny jeans are the best jeans to go with any ankle boots and Chelsea boots are not an exception. They are easier to tuck into your boots or sometimes do not even require any tucking in at all. A cute Fall outfit you can easily create is pairing your black jeans with your black ankle boots and a chunky sweater in the color of your choice.

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This is a look you could wear for a causal date night or to a pumpkin patch. You could also opt for a form-fitting sweater instead and add a black leather jacket for a sleeker look. Of course this look also works with a pair of blue jeans.

3) Chelsea boots and dresses

If you’re looking to create formal outfits with your Chelsea boots, you may want to try pairing them with a midi or maxi dress. A sleek leather Chelsea boot would look great with a pleated midi dress and a pair of black tights when it’s a bit chilly outside. You could layer this look with a cardigan or longline coat.

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When creating dressy outfits with Chelsea boots, think sleek boots in a neutral color. If you’re going with a maxi dress, remember that most likely only the front or top of the boots would be showing and so you want this to look as sleek and chic as possible to really give that formal vibe.

4) Chelsea boots and maxi skirts

Along the lines of the Chelsea boot and maxi dress look, we have the maxi skirt. The difference here is that the maxi skirt can be dressed up or down to create different looks. For a more casual look, try pairing your black leather Chelsea boots with a black maxi skirt and a white t-shirt. You could throw on a denim jacket to complete this look.

Get the look HERE

Another great way to style the maxi and Chelsea look in a casual way is to wear a cropped top with a light cardigan, if needed. You could add a long necklace as well to create more boho vibe. If dressing for the cold weather, replace your t-shirt or top with a sweater in a bright color to add a pop of color to your look.

5) Chelsea boots and leggings

As someone who lives in leggings all winter long, this is probably my favorite way to style Chelsea boots. To bring out your inner rocker, style your black leather Chelsea boots with a pair of leather leggings and an oversized graphic tee for karaoke night with the girls. Don’t forget the leather jacket! You could also try pairing your boots with a pair of tights and a sweater dress if you’re headed somewhere more fancy than the bubble tea spot around the corner.

Image source here

When you really don’t know what to wear with your Chelsea boots and are unsure what the dress code of the place you’re heading to is, a pair of black leggings and an oversized sweater is always a safe bet. Not too dressy and not too casual neither.

6) Chelsea boots and a pair of pants

For a choc corporate look, pair your Chelsea boots with dress pants and either a white blouse + a blazer or shirt in a neutral color with a structured blazer. This is also a look comfortable enough that you can wear it to commute to the office without having to change into a different pair of shoes. For a more preppy vibe, consider draping a cardigan across your shoulders and tying its sleeves at the front.

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To create a unique look with your Chelsea boots, try opting for a pair of culottes instead of a pair of full trousers. You could go for a pair of high boots in this case and then top it off with a blouse and trench coat as outerwear.

I hope you have gotten many outfit ideas from these simple options. It’s amazing how many outfits you can create with just a few key pieces you most likely already own.

I encourage you to invest in a pair of quality Chelsea boots which you would be able to wear in the cold weather as well as some warmer days. They’re such a stylish boot that’s so easy to dress up or down.

If you enjoyed this post, you’ll definitely be interested in my post on Black Ugg boots outfits.

You can also check out my post on how to wear maxi dresses in the Fall HERE.

For some outfit inspiration when it comes to pairing cowboy boots, check out my post: The best women's jeans to pair with cowboy boots.

If you're looking for some outfit inspo when it comes to wearing any Chelsea boot, check out my post: 13 Stylish Outfits to Wear With Chelsea Boots.

Until the next post,



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