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I absolutely love chelsea boots! I fell in love with them while living in the UK and they’ve now become a staple in my everyday wardrobe. As a plus, they’re perfect for travel because they traditionally have a slip-on design making them easy to take on and off at airport security. Take a look at the womens chelsea boots we’ve rated as #1 in style, comfort, AND function, too.
Best Chelsea Boots for Women
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Ankle boots are some of the most ideal footwear options for travel, especially if you’re headed to destinations with cool weather or are traveling in between seasons. Not only are they easier to pack than tall boots, but the right pairs offer waterproof materials and rubber soles creating the perfect trifecta of the most important things to look for in a sightseeing shoe.
My cozy chelsea boots outfit traveling from London to Paris on the Eurostar (similar style)
Wear Chelsea boots with jeans or leggings for a casual but stylish look or dress them up with tights and a dress like my outfit above. These chic slip-on boots are ultra-versatile and will up level any travel outfit.
What’s the most cute and comfortable Chelsea boot? Find out below!
Most Popular Chelsea Boots Womens Style: Sorel Joan Now
Practical and pretty, the Sorel Joan Now is a huge reader favorite for travel! The design is sleek and versatile, with a luxurious waterproof exterior, so perfectly complement both casual and dressy outfits.
They’re extremely comfortable to walk in, with a stylish lug sole adding plenty of traction and stability on rough or slippery streets. This pair continually gets the readers’ top vote as the most comfortable chelsea boots womens style of all time!
Kenneth Cole Reaction Salt Chelsea Ankle Boot
Classic Black Chelsea Boots Women Love: Kenneth Cole Salt
This timeless style by Kenneth Cole is the perfect representation of the classic Chelsea design. At roughly $100, these leather boots are an incredible value. They’re chic, sophisticated, well-made, and beautiful.
This is a fantastic everyday shoe you can walk miles in on the streets of NYC, wear to work, or use as an elegant yet comfortable travel shoe. Women love these boots for their elegance, simplicity, and comfort.
When it comes to shoes, it’s vital for feet to feel comfortable at all times. Readers swear by shoe inserts to help boost support for long periods of walking!
Shop Sorel Emelie III Chelsea: Amazon | Sorel
Leather Brown Chelsea Boots for Any Terrain: Sorel Emelie
Travelers love Sorel boots, especially for wet, snowy, cold, and extreme winter weather. For sturdy traction that will keep your feet dry in any rainy conditions, readers recommend the popular Sorel Emelie Waterproof Bootie!
These full-grain leather Chelsea boots have a synthetic rubber made to handle a variety of terrain. But they’re not just rugged in durability; they also have a cushy molded footbed, making them comfy enough to walk all day! And TFGs love their cute style, too.
Find out why our readers vote Sorel as a top travel footwear brand, and take a look at their top picks for sneakers, sandal and boots!
Shop Sam Edelman Laguna Chelsea: Amazon | Nordstrom | Zappos
Cute Waterproof Chelsea Boots: Sam Edelman Laguna
These Sam Edelman Chelsea boots have that classic look but are elevated with a sleek leather exterior, a chunky lug sole, and a pop of brown leather trim for some stylish contrast. These beauties have stretchy gore at the side for easy on and off, and wearers rave about the comfort, sharing that they can walk forever in them!
Blondo Dagger Waterproof Ankle Boots
Chic Tan Platform Chelsea Boots: Blondo Dagger
Another cute and comfortable style is these Blondo tan Chelsea boots. This pair is waterproof, easy to slip on and off, and features a sturdy rubber sole that’ll handle slippery or slushy streets.
Whether you are planning to enjoy the streets of London all day long or want some stylish sightseeing shoes, these boots are said to be comfortable, soft to wear, and will keep your feet dry in a downpour!
Shop Dr. Martens Boots: Amazon | Dr. Martens
Comfortable Classic Women’s Chelsea Boots: Dr. Martens 2976
This fashion-forward shoe is as practical as it is comfy, making the Dr. Martens 2976 a perfect travel boot. The particular style adds some edgy fun to travel outfits, yet wearers report that these Chelsea boots are durable and feel great on, even after several hours.
If you’re looking for a responsible, fashion-friendly choice, these Dr. Martens vegan Chelsea boots are for you!
For more ideas, these are the best black ankle boots for sightseeing!
Eddie Bauer Bellingham Chelsea Boot
Stylish Suede Chelsea Boots: Eddie Bauer
We are in love with the Eddie Bauer chunky heeled Chelsea boots! They’re so stylish and practical. The water-resistant suede upper can handle all kinds of weather, and the sturdy sole will keep your feet firmly planted on the ground.
Users say these are durable, cute, and so on-trend. They also pair well with everything from dresses to slim jeans!
Looking for knee-high boot suggestions? Here are our top picks!
Blundstone Unisex 558 Chelsea Boot
Outdoorsy Black Chelsea Boots: Blundstone 558
When asked about Blundstone boots for traveling, readers agree: these booties were made for walking! These are particularly awesome if your trip includes outdoor activities. No need to pack hiking boots plus sightseeing shoes – this one pair can do both.
Despite not having major arch support, travelers still say they’re surprisingly comfortable. They mention that they provide great ankle support, mold to your feet, and are water-resistant. They’re available in many sizes for both men and women.
Shop Born Cove Boots: Amazon | Nordstrom | Born
Light Brown Chelsea Boot Women Adore: Born Cove
Born brand is a long time reader favorite and their Cove Chelsea suede boot is sure to become one of their newest must haves.
While it’s not officially available in wide widths, it does have a wider toe box if you’re not a fan of almond or pointy-toe boots. They’re also made to withstand the rain and boast a removable sole with arch support.
Prefer the look of lace-up boots? Check out these top-rated ankle combat boots that you’ll need for those colder climates!
Nordstrom Miah Chelsea Lug Boot
Gorgeous Black Leather Chelsea Boots: Nordstrom Miah
Nordstrom’s Miah Chelsea boots are an elevated take on the classic style, with a block heel and a lug platform sole. Made of quality, water-resistant leather, this pair will see you through rainy days and always keep you grounded. Wearers say they’ve walked miles and miles in these shoes with comfort and love how easy they are to dress up!
Packable Cute Chelsea Rainboots: Asgard
Rain boots are too bulky to pack in a carry-on, but if you’re headed to a rainy and muddy location, the Asgard Chelsea Rain Boots are your best bet for traveling light. These beauties have elastic side panels for easy wear, a sleek design, and a non-slip sole, combining practicality and fashion for rainy days.
However, if you’re looking for a boot that will be comfortable enough for long hours of sightseeing, we recommend these cute, comfortable, and waterproof leather boots instead.
For more ideas, take a look at these ankle-length rain boots!
How to Choose the Best Womens Chelsea Boots
My airport outfit with Chelsea boots (similar), jeans, blouse, and a leather jacket
What Are Chelsea Boots?
The classic Chelsea boot is a pull-on style shoe characterized by elastic side panels, a suede or leather upper, and a low stacked heel, though we see a bit more variety these days.
Chelsea boots were traditionally worn by men. They had a leather upper, a latex sole, and a tiny heel. Since then, they’ve been adopted by everyone and have become a stylish option for women.
Though distinguished by a pull-on style, modern Chelsea boots might have a zipper. Overall, they can be really handy boots to wear in airports when going through security. If you’re wondering about wearing your boots on a plane, our readers offer their advice!
In San Diego wearing cChelsea boots (similar) with Zella leggings, black tank, Top Shop maxi dress, and Rebecca Minkoff Julian
How to Wear Chelsea Boots?
The best thing about womens Chelsea boots is that they’re very versatile! A few of my favorite outfit ideas are:
- Long sweater or tunic worn over leggings
- Long sleeve tee or blouse tucked into a mini skirt or dressy shorts with tights
- Loose fitted button down top with skinny jeans
- Fitted midi-dress and leather jacket
- A-line dress and blazer or sweater coat
The main thing to note is that a tan leather Chelsea boot has the most iconic design, and the color works well with everything – even an all-black outfit!
What are your tips on how to wear Chelsea boots? Please share your comments below!
For more travel boots, please read:
- Best Ankle Boots for Fall
- Women’s Waterproof Leather Boots
- Best Ankle Boots for Travel to Europe
- Most Comfortable Black Ankle Boots
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Author Bio: Niki is an interior designer and artist from Louisiana. In addition to her design work, she writes for local and online publications sharing her experiences and passion for travel. Niki is currently adding stamps to her passport while building her design practice, Niki Landry Designs.
Love my Chelsea boots – I have the Blundstones and Blondos. They are the best for traveling and staying dry and warm while walking around in rain/slush. I do struggle to style them though…with cute outfits.
Love my Sorel boots!
I’m headed to Germany for the a week of Christmas markets! I want to go carry on only and needed to find the perfect waterproof boot. Love that you tell us how to style the shoes and not just compare them!
The best thing is that the selection of ankle boots appeals to young and old as well as narrow or wide foot. I love that Alex and company does all the work and I can reap the benefit!
This Florida girl is looking for Chelsea boots for some fall travel and this was so helpful, as so many of the posts are:)
Loves my Sorel boots on my recent trip to Ireland. So comfy and kept my feet dry.
Hi! We are headed to Ireland end of august. Any vegan recommendation for comfortable, cute shoes for long hours of wear/walking?
Hi Trang, we have a range of recommendations for vegan shoes here: https://www.travelfashiongirl.com/best-vegan-shoes-womens/
You might also find this post helpful for tips for how to choose the best shoes for Ireland: https://www.travelfashiongirl.com/best-shoes-for-ireland/
Hope this helps and have an awesome time on your trip!
What do you recommend for Vienna in April?
53 year old woman never been to Europe
Hi Kate, thank you for your question! Take a look at this article on What to Wear in Austria: https://www.travelfashiongirl.com/what-to-wear-in-austria/. This article might also be on some help: https://www.travelfashiongirl.com/ultimate-packing-list-for-women-over-40-mixed-weather-travel/ Hope these are useful. Also this is a helpful guide that explains more about how to use our packing guides lists https://www.travelfashiongirl.com/how-to-use-the-travel-fashion-girl-packing-lists-and-guides/ Hope this helps! 🙂
My main concern is comfort, since I expect to be walking a LOT. I’ve never been comfortable in heels. Usually I go for ballet flats (and I’ll probably bring those as a second pair), but I wanted something different and more weather-proof for London in March. Any suggestions for boots that were made for walking? (Ha ha.)
I finally purchased a pair of Blundstone Chelsea boots in the cream color as an all-around travel and weather friendly pair due to the extra toe room and minimal heel. You could add inserts for extra comfort. They are water resistant. Born also makes a cozy Chelsea boot if you have more narrow feet/less toe splay. I loved their version too, but they didn’t fit my feet. The main thing is to break them in slowly at home on walks in increasing lengths before wearing them on a trip. Unfortunately, they don’t break in easy. Mz Mooz is my other brand for softer, ready to wear boots. Have an amazing trip when you go!
These are all such beautiful choices! As much as I try to wear boots like these with skirts, it always looks like I am trying too hard! I would love to see a post on travel boots that have a bit more of a feminine vibe!
We actually have a few posts with a lot of different boot suggestions, like this one: https://travelfashiongirl.com/best-travel-shoes-womens-leather-boots/ or this one: https://travelfashiongirl.com/best-ankle-boots-for-fall/ Happy shopping and traveling!
Tilly’s has Chelsea boots and they are a great option for only $30! The brand is SODA.
Oh thanks for the recommendations Rachel!