How to Wear Chelsea Boots (with Jeans, a Dress, and Leggings)

Chelsea boots are the kind of shoes you know you need in your closet but each time you pull them out, you struggle to style them. Trust me, I get it. I love my Chelsea boots, especially in the cold winter months, but it took me some trial and error to figure out what they looked good with. And to be honest, they can be a bit finicky to style since the hem length is pretty important with that style of boot. But once you know how to style them, Chelsea boots become a timeless wardrobe staple that pairs effortlessly with almost anything—from dresses to jeans. Their sleek, ankle-high silhouette, elastic side panels (or side zip), and versatility make them a must-have for any fashion-conscious closet.

In today’s post, I’ll share my favorite Chelsea boots and provide styling tips for all kinds of outfits, whether you’re working with skinny jeans, straight-leg pants, skirts, or tights. Let’s jump in!

How To Wear Chelsea Boots With Jeans, A Dress, And Leggings

My Favorite Chelsea Boots 

Let’s start with my go-to Chelsea boots. My favorite pair is the Miah Water Resistant Chelsea Lug Boot sold at Nordstrom. They are made with weather-resistant leather that’s boosted by a hardy lug platform and block heel. The ankle isn’t short but it’s also not too tall, which makes it easier to style with multiple outfits. This pair of boots is especially comfortable, and for the price, you just can’t beat them. I own the black pair and think black or tan is the most versatile, but if you want something bold, a white or burgundy pair can be a fun addition to your rotation.

I’m linking the Miah boots along with a handful of other cute boots below. I do want to note, however, that if you don’t own any Chelsea boots, I actually think the Downtown Boot from Margaux is a better option than true Chelsea boots. They’re a bit slimmer and easier to style, so I wanted to add that note here in case you’re shopping. (You can see how to style more ankle boots with jeans in this post.)

But, if you already own Chelsea boots and don’t know how to style them, read on!

What Socks to Wear With Chelsea Boots

Socks can make or break the comfort of your Chelsea boots (and warmth), but they’re also an easy way to change the style of your outfit. Sometimes, the outfit will look best if the socks are hidden, and other times, a little peep of your socks will look better, so you’ll want to have a few different options.

I often wear ruffled socks that peek out for an unexpected touch. When it’s freezing, I prefer thicker socks. The key is to balance the rest of your outfit with the boots, and the socks will also play into that. I’ll get more into this below.

What Kind of Pants Can You Wear With Chelsea Boots?

One of the most common questions is, “What jeans go with Chelsea boots?” The beauty of Chelsea boots lies in their versatility. You can pair them with various pants and jeans, but the styling and hem length are key.

• Skinny Jeans: Find a pair of super skinny jeans that hits right at the top of the boot for a sleeker look
• Straight-Leg or Kick Out Crop Jeans: Let the hem graze the top of the boots or cover the shaft of the boot just a bit.
• Wide-Leg Pants: Allow the wide-leg jeans (or wide-leg trousers) to drape over the boots. Floor length is best.
• Flared Jeans: Let them fall naturally over the boots. Floor length is best.
• Cropped Jeans: Highlight the boots by exposing a sliver of the ankle.
• Leggings: Always tuck the leggings into the boots and ensure no skin is showing near the ankle.

How to Style Chelsea Boots With Leggings

Leggings and Chelsea boots are one of my most-worn combos. A few styling tips: 

• Pair black leather Chelsea boots with black leggings for a sleek, monochromatic outfit. I shared my favorite leggings in this Amazon leggings roundup.
• Add socks that peep out of the top of your booties to break up the look or hide them for a sleek, monochromatic look. (Try ruffled socks for an unexpected style moment!)
• Add an oversized sweater, a cropped puffer (see my round up of the cutest puffer coats here), or a long coat to balance the weight of the shoes. I also shared my list of the best winter coats for all occasions here.
• See a video where I walk through how to style leggings with Chelsea boots here.

I also shared how to style leggings for all occasions in this post.

How to Style Chelsea Boots With Skinny Jeans

Wearing Chelsea boots with skinny jeans is a classic pairing – and skinny jeans are actually coming back on trend. (Despite them being very off-trend a few years ago!) I’d just find a way to make the rest of the outfit look intentional and on-trend and not dated. Here are a few tips to style them: 

• Make sure they are TIGHT at the ankle and the hem hits right at the top of the boots. I find that many skinny jeans are actually not tight enough and create a bulky ankle, and I find that tucking jeans into the boots looks sloppy. You can try a cuff (you can see mine are cuffed below, but tucked under) but ideally, you want to avoid adding any bulk!
• Pair with an oversized sweater for a relaxed outfit or a blazer for a chic, layered look. (Add a belt and a tucked-in top to define your waist.) I shared my 10 favorite affordable sweaters (that don’t feel cheap) in this blog post.
• Pair with a fitted turtleneck and cropped puffer. 
• See a video where I walk through how to style skinny jeans with Chelsea boots here.

See my post on how to style black jeans here.

How to Style Chelsea Boots With Straight-Leg Jeans or Kick Out Crop Jeans

Straight-leg jeans and kick out crop jeans are having a major moment, and they look fantastic with Chelsea boots. To style them:

• Choose cropped straight-leg jeans or roll the hem of the jeans to show the top of the boots. You don’t want your ankle to show, so have the cuff of the pants kiss the top of the boots.
• For Kick Out Crop jeans, just find a pair that hits right at or covers just the top of the shaft of the boot. The goal is to see the majority of the shoe with this look, but you don’t want to see too much ankle.
• Pair with a structured blazer or leather jacket for a polished outfit that looks intentional and not sloppy.
• See a video where I talk through styling kick flare jeans with Chelsea boots here.
• You can see my favorite straight-leg jeans in this post.

How to Style Chelsea Boots with Flare Jeans

Flare jeans are actually quite easy to style with Chelsea boots. Here’s how:

• Make sure your jeans are hemmed so that they just barely graze the floor when you’re wearing your boots.
• Choose a more casual top than you normally would for flare jeans since Chelsea boots lean more casual.
• Dress up the look with a fun jacket to help balance the width of the flare!
• Here’s a video where I walk through styling tips for flare jeans and Chelsea boots.
• Here’s a blog post with my favorite ways to style flare jeans.

How to Style Chelsea Boots With Wide-Leg Jeans

Styling Chelsea boots with wide-leg jeans creates a chic, relaxed look that’s on-trend, comfortable and practical.

• Choose ankle-length or slightly cropped wide-leg jeans to let the boots peek through. Again, we don’t want much ankle showing, so the hem of your pants should be right around the top of the boots.
• For longer jeans, the hem should skim the ground without dragging, like I’m wearing below.
• Always tuck in your top (if it’s a loose blouse or a fitted top) or wear a cropped sweater to balance the volume of the wide-leg silhouette.
• Add a structured blazer or cropped jacket for a polished finish.
• I walk through styling wide leg jeans with Chelsea boots in this LTK video.
• You can see more styling tips for wide leg jeans in this post.

Tips for Wearing Chelsea Boots With Skirts and Dresses

Chelsea boots aren’t just for pants—they can be paired with skirts and dresses. The key is balancing the weight of the shoes with the rest of your outfit (either with material or layers or both) so the shoes don’t look too heavy. I do have to note that I don’t personally love how Chelsea boots look on me with dresses. The boots hide the thinnest part of my ankle, so I don’t love how they look when I wear dresses since it cuts off my legs at an unflattering spot. However, when I do wear Chelsea boots with dresses, I always wear a chunky sock that shows to balance the shoes, or I’ll wear tights to elongate my legs. Here’s how to make it work:

• Mini Skirts: Choose a skirt with a heavier fabric like tweed or wool. You can style it with tights or bare legs. 
• Midi and Maxi Dresses: Opt for a sweater dress with tights. Or, go for a flowy dress to contrast with the structured boots and layer a heavier jacket or cardigan to balance the look. 
• Pleated Skirts: Pair with chunky Chelsea boots and a sweater for a feminine but practical look.

Experiment with what looks best for your proportions and outfit, always keeping balance in mind. I shared a video on LTK where I styled Chelsea boots with dresses here, and here’s one where I styled the boots with a skirt. If you want more ideas of how to wear booties with dresses (and what booties I like best), read this post about pairing boots with dresses.

How to Style Chelsea Boots With Tights

Tights and Chelsea boots are a match made for colder weather. Here’s how to style them:

• Pair black tights with black Chelsea boots for a sleek, elongating look.
• Consider wearing a mini or midi skirt along with the tights. This balance will translate well with the boots.
• Layer socks over the tights for extra warmth. This looks best if the rest of your outfit has a few layers to balance the look. (Think a collared shirt under a sweater.)

FAQ:

Do Chelsea Boots Go Over or Under Jeans?

This depends on the type of jeans:

• Skinny Jeans: You can tuck them into the boots, but make sure there’s no bunching or gathering. If needed, create a small cuff at the bottom to create a more streamlined look. Ideally, the hem will hit right at the top of the jeans.
• Straight-Leg Jeans: They can go over or just touch the top of the boots. Avoid them touching the top of your foot– you want them just a little bit shorter.
• Wide-Leg Jeans or Flare Jeans: Go over the boots to maintain the flow of the pants. It’s best if they are a bit longer than you’d want for straight-leg jeans; they should hit the top of your foot and potentially even kiss the floor.

It may take some trial and error in your own closet to determine what looks best on your figure, but testing out the jeans you already own is a great first step.

What Not to Wear With Chelsea Boots?

While Chelsea boots are versatile, there are a few looks to avoid:

• Pants with overly long hems that bunch around the boots.
• Skirts or dresses with awkward mid-calf hemlines that cut off the silhouette.
• Trousers – you can style Chelsea boots with trousers, but it takes a very specific cut and style. Most work trousers that are straight-leg or ankle-tapered don’t pair well with Chelsea boots. 

Are Chelsea Boots Still in Style in 2024?

Yes! Chelsea boots remain a timeless staple in 2024 and beyond into 2025. Their versatility, comfort, and ability to adapt to modern trends earned them their spot as a wardrobe essential. Chunky-soled versions are trending, but classic leather Chelsea boots will always stay in style. Whether you’re looking for a casual or polished look, these boots are a solid investment.

Shop The Post