how to wear Chelsea boots

20 Outfits for How to Wear Chelsea Boots with Style

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Chelsea boots are a classic style that’s been trending big in the last few years.  And for good reason! In the fall and winter months, they’re a great flat pair of boots to wear with casual outfits and even to work.  

Originating in the mid-1800s, the Chelsea boot was initially a riding boot. Queen Victoria needed a flat boot that she could easily slip on and off. The elastic side panel provided a great solution.  Today these ankle boots are a comfortable and versatile modern-day option!

In this post, get inspired by 20 Chelsea boot outfits made with jeans, pants, and dresses. But first, here’s a roundup of the best Chelsea boots.

The best Chelsea boots

In the stores these days, you’ll see black leather Chelsea boots with lug soles. The black color and thick soles give them an edgier feel. You’ll also find burgundy brown Chelsea boots that give a more classic feel. Tan suede boots work great with cozy sweaters and flannel shirts. Streamlined and slim-toed Chelsea boots are a bit more elevated and work for more formal looks.  Choose platform Chelsea boots for a bit of height and with wide-leg pants.

When you buy Chelsea boots, make sure they have just a small gap between your ankle and the top of the boot. If the boots are looser and you look like you’re swimming in them, wear them with a short pair of boot socks like these.

How to wear Chelsea boots

Do Chelsea boots go with anything? 

Wear your Chelsea boots with just about anything. They are versatile boots that work great with many styles of jeans, pants, sweater dresses, and even midi dresses in the colder months. 

In this post, I’ll be styling a burgundy pair of Chelsea boots I picked up at the Nordstrom Anniversary Sale. I also style a few outfits with a pair of black Chelsea boots with a 3-inch platform heel.

Ready to see the best way to style these boots.? Let’s dive into looking at Chelsea boots with jeans, then we’ll look at pants and dresses.

How to wear Chelsea boots with jeans

With black kick crop jeans and a blue and white striped button down

A great way to wear your Chelsea boots is paired with your ankle-length or cropped jeans. Let the hem of your jeans come down over the top of your boot. It can also stop just above the top of the boot. You don’t want to have too much space between the top of the boot and your hem because that makes it look like you’re wearing high-water pants.

With black kick crop jeans and a blue and white striped button down

Boots | Belt | Jeans | Shirt | Bag (old)

Choosing burgundy-brown Chelsea boots over black boots offers a third color to this outfit, which makes it even more interesting. Matching your belt, boots, and bag is the best way to ground the look and helps the burgundy boots make sense in the look. 

With black kick-crop jeans and a gray turtleneck sweater 

Here’s another look with a chunky gray turtleneck sweater. Front tuck the sweater to show your belt.

With black kick-crop jeans and a grey turtleneck sweater

Boots | Belt | Bag | Jeans | Similar Sweater

This quilted bag has a Hermes-inspired two-tone strap that blends perfectly with the belt and boots. 

With straight jeans and a black sweater

Here’s a pair of blue jeans with these Chelsea boots. They’re labeled kick crop jeans but are actually straight leg jeans because the leg is straight up and down between the hem and knee. Again, the hem comes just below the top of the boots.

With straight jeans and a black sweater

Boots | Bag | Jeans | Sweater

I’m wearing a chunky oversized black sweater and that belt bag for some contrast.

With black kick-crop jeans and a Breton stripe sweater

You know I can’t resist making a look with my Breton stripe sweater! Stripes are a quick and easy way to add visual interest to a look.

With black kick-crop jeans and a Breton stripe sweater

Boots | Belt | Jeans | Similar Sweater

With black kick-crop jeans and a cream sweater

I shared this sweater in my Nordstrom Anniversary try-on post. I love how it elevates a look, with those slightly longer sleeves. You definitely need to pull them back when you eat and you won’t want to wash dishes in this sweater. But they make the look a little bit special.

With black kick-crop jeans and a cream sweater

Boots | Belt | Jeans | Bag | Sweater

With black kick-crop jeans, a black cardigan, and an olive green quilted jacket

A column of black with black jeans and a black sweater is super chic. Adding an olive jacket and these brownish Chelsea boots and a belt elevates the look even more. I gave the cardigan a front tuck to show the belt and define my waistline.

With black kick-crop jeans, a black cardigan, and an olive green quilted jacket

Boots | Belt | Jeans | Similar Cardigan

With wide-leg jeans and a white tee

Can you wear your flat Chelsea boots with wide-leg jeans? Absolutely! Since wide-leg jeans are baggy and have quite a bit of fabric in them, an easy way to style them is with a fitted top. That helps to define the upper body and waist.

With wide-leg jeans and a white tee

Boots | Belt | Jeans | Shirt

With wide-leg jeans, a white tee, and a navy coat

If you tend to wear fairly simple outfits, adding a long statement coat over top immediately creates an elevated and stunning look. This navy coat makes the look come alive as the eye gets drawn up and down the body from the collar to the hem of the coat. 

With wide-leg jeans, a white tee, and a navy coat

Boots | Belt | Jeans | Shirt | Coat

With wide-leg jeans and a white button-down shirt

Here’s another look that pairs a classic white button-down shirt with those same wide-leg jeans. Roll up the sleeves on your shirt to create a laid-back feel. Since rolled-up sleeves stop around the waistline, it also draws attention to and helps to define your waist.

With wide-leg jeans and a white button-down shirt

Boots | Belt | Jeans | Similar White Shirt

With wide-leg jeans and a textured sweater

Here’s another sweater that I showed in my Nordstrom Anniversary Try-ons post. I love it because it’s got texture in spades so it instantly adds visual interest to a simple outfit. It’s also a little bit shorter, which works well with high-waisted jeans. Especially if you’re front tucking it like I am here. There’s less bulkiness at the waistline.

With wide-leg jeans and a textured sweater

Boots | Belt | Jeans | Sweater

With wide-leg cropped jeans, a navy sweater, and a navy blazer

I was wondering if my legs would look short and stumpy if I paired my wide-leg cropped jeans with these Chelsea boots. And I’m not hating the look. As compared to when I tried these jeans with some Western ankle boots and I looked like I was wearing gauchos in a bad way. Classic styles of boots keep the overall look classic.

With wide-leg cropped jeans, a navy sweater, and a navy blazer

Boots | Belt | Jeans (sold out) | Similar Sweater | Blazer

If you wanted a trendier and edgier look, throw a Rolling Stones t-shirt under the blazer.

With wide-leg cropped jeans and a chambray shirt

Monochromatic looks and denim on denim is an easy way to go when you’re not sure what to wear. I tucked in this casual shirt all the way around and rolled up the sleeve to define my waistline.

With wide leg cropped jeans and a chambray shirt

Boots | Belt | Jeans (sold out) | Belt Bag

Instead of a chambray shirt, you could wear a flannel shirt here. 

With wide-leg jeans, a turtleneck sweater, and a camel overcoat

In this look, I’m wearing a chunky gray turtleneck. I love combining this light gray color with camel for an interesting contrast. The camel overcoat elevates the look.  

With wide-leg jeans, a turtleneck sweater, and camel overcoat

Boots | Belt | Jeans | Similar Sweater | Similar Coat

With bootcut jeans and a tan cardigan

When I put on my bootcut jeans with the Chelsea boots and a belt, my lower half felt kind of rugged to me. I choose this deep v-neck cardigan to show a little more skin and lighten up the look. Cargo pants would be another great option with these boots if they fit your sense of personal style. Just like with the bootcut jeans, it will create a rugged look on the bottom so you’ll want to wear something slim-fitting up top and perhaps show a bit more skin. 

With bootcut jeans and a tan cardigan

Boots | Belt | Jeans | Bag | Similar Sweater

How to wear Chelsea boots with pants

Let’s look at Chelsea boots with pants now! First up, an unexpected look.

With black sweatpants, a black sweater, and trench coat

If you want a more casual look for a Saturday of running errands, grab a pair of black sweatpants or leggings, combine it with a chunky black sweater, and add a statement trench coat over top. Instead of grabbing sneakers, throw on your Chelsea boots for an elevated look you’d feel comfortable wearing into a restaurant if you stop for lunch. 

With black sweatpants, a black sweater, and trench coat

Sweatpants | Sweater | Boots | Trench Coat

These sweatpants are the perfect length because they end at the top of the boot.

You could also wear black leggings here. It’s fine if a short pair of socks stick out of the boot and overlap with your leggings.

With black trouser pants and a grey sweater

Here I’m wearing my black platform Chelsea boots that have a 3-inch heel on them. I like the height they give to these long dress pants. They don’t get lost in the hemline. This becomes a look you can wear to business meetings. As a bonus, these boots are waterproof so they can work on cold and wet days. 

With black trouser pants and a grey sweater

Boots | Similar Trouser Pants | Sweater (Old) | Bag

With black trouser pants, a white tee, and a brown leather jacket

In this look, I’m wearing the same black trousers. This time I’m wearing a long-sleeve white t-shirt and a brown leather jacket for an elevated edgy look. Swap out the white shirt for a black t-shirt to elevate the look even more for a night out. 

With black trouser pants, a white tee, and a brown leather jacket

Boots | Similar Trouser Pants| Shirt | Bag

How to wear Chelsea boots with dresses

Now let’s see a few dress looks!

With a Breton stripe sweater dress and black utility jacket

If you’ve been following my blog for a little while, you know about my love of Breton stripes. I snagged this sweater dress and this casual jacket from the Gap this summer. For Gap sweater dresses, I buy them in the tall length so they come to my knee at 5’6″.

With a Breton stripe sweater dress and black utility jacket

Sweater Dress | Jacket | Boots | Similar Belt Bag | Similar Belt Bag

Pairing a sweater dress with black platform Chelsea boots is a natural combo and creates a laid-back and cozy fall vibe.

With a black sweater dress and denim jacket

Let’s see these boots with a black turtleneck sweater dress. You may wonder if flat Chelsea boots look clunky with a knee-length dress. They’re streamlined enough and hit at a slimmer spot on the ankle so it works. 

With a black sweater dress and denim jacket

Boots | Similar Dress | Jacket | Bag

With a floral midi dress

It’s super trendy to pair your Chelsea boots with a midi dress that comes down below the knee for a laid-back fall look. Just like it’s trendy to wear white sneakers with a dress, combining casual boots with a dress creates a laid-back, stylish, and comfy dress outfit. There’s a tension that’s created when casual and dressier pieces are paired together that is very intriguing to the eye. When you choose your dress, look for one with some waist definition. This dress has a seam at the waist that helps to define the waistline, as do the ¾-length sleeves. They also draw the eye to the waist.

With a floral midi dress

Boots | Bag

This look works because the top of the boot hits at a slim part of the ankle and hugs it with only a small gap. If you have a larger gap, wear a short but visible pair of socks that are a similar color as the boot or your legs. 

You can also try this look with a slim-fitting midi dress.

Infographic for how to wear Chelsea boots

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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