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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 thing 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 mini-dress like my outfit above. These versatile slip-on boots are ultra-versatile and will uplevel any travel outfit.



What’s the most cute and comfortable chelsea boot? Find out below!




Kenneth Cole Reaction Salt Chelsea Ankle Boot


The Classic Black Chelsea Boots Women Need in their Everyday Wardrobe: Kenneth Cole Salt


I had to start the list with the epitome of chelsea boot perfection and this timeless style by Kenneth Cole is the perfect representation of the classic chelsea design. You bet I bought them as soon as I saw them! The black microsuede color is the perfect replacement for the Kurt Geiger style I’m wearing in the top picture!

At roughly $100, these leather boots are an incredible value. They’re chic, sophisticated, well made, and absolutely beautiful. This is a fantastic everyday shoe that you can walk miles in on the streets of NYC, wear to work, or use as elegant yet comfortable travel shoes. 

Best for a narrow to medium fit, choose from ten colors, they’re available from sizes 5-12! Women without foot issues love these boots and rave about being able to walk in them all day. 


If you need arch support or aren’t used to being on your feet for long sightseeing days, keep reading our list below because we have a range of options from comfort shoe brands including the top selling Teva boot below!




TFG Readers Pick: Teva Anaya Chelsea Boot


Most Popular Chelsea Boots Womens Style According to the Readers: Teva Anaya 


For a practical and casual option, the Teva Women’s Anaya is a good choice for you. It’s sleek, practical, and cute. It’ll make the perfect compliment for your overseas or autumn adventures. 

They’re lined and waterproof with rubber sole for stability – ideal shoes if Ireland’s your destination. TFG readers love the Anaya- the shoe continue to get the readers’ top vote as the most comfortable chelsea boots womens style of all time!





Dr. Martens Flora Chelsea Boots


Comfortable Women’s Chelsea Boots: Dr. Martens Flora


This fashion-forward shoe is as practical as it is comfy, making the Dr. Martens Flora a perfect travel boot.

Dr. Martens are a much loved brand across the world for their famous air-cushioned sole. The above style, in particular, is awesome for adding a touch of edge to your look.

Because of their durability and superior comfort, you can walk in them over salty sidewalks, through snow and rain, and your feet will stay comfortable and warm, all while looking good!

If you’re on the hunt 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!




Blondo Dagger Waterproof Ankle Boots


Cute Waterproof Chelsea Boots: Blondo Dagger


Blondo is by far the most popular brand for travel boots! The majority of their styles are waterproof and many have light rubber soles making them perfect for light rainy days. The Blondo Dagger shown above has a modern chelsea inspired design, but has a zipper on the side making it just as easy to remove after a long day on your feet.


Read our review for the Blondo Boot Villa, the most popular waterproof ankle boot according to the readers!




Eddie Bauer Bellingham Chelsea boot


Stylish Suede Chelsea Boots: Eddie Bauer


We are in love with the Eddie Bauer Chelsea Ankle Boots! They’re so stylish I can’t believe they’re actually practical, too. They pair just as perfectly with leggings and a long sweater in the winter as they do with a short skirt and tights in the spring. Dress them up, dress them down, wear them to dinner with your friends at home, or take them on your trip abroad, this slip-resistant rubber soled boot will absorb the shock of the cobbled streets in Europe and they’ll do it in style. 

The water-resistant suede upper is perfect for all kinds of weather and has a sturdy sole with a strong grip to lead you safely down the Champs-Élysées. If you’re looking for what to wear in London in Summer or Los Angeles in Spring, these fashionable chunky heeled chelsea boots are a top pick for your travels near or far!


Looking for knee-high boot suggestions? Here are our top picks!




Sorel Emelie Chelsea Boot


Leather Brown Chelsea Boots for All-Terrain: Sorel Emelie


Travelers love Sorel boots especially for wet, snowy, cold, and extreme winter weather. For a boot with sturdy traction that will keep your feet dry in the light to heavy rain, we recommend the popular Sorel Emelie Waterproof Bootie

They have a synthetic rubber made to handle a variety of terrain. But they’re not just rugged in durability, they also have cushy moulded footbeds, making them comfy enough to walk all day!

We love the rich dark brown leather style shown above, but these full-grain leather chelsea boots are also available in black, grey, and various tan shades. 


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!




Born Cove Boots


Light Brown Chelsea Boot Women Love: 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. Available in four colors, this suede waterproof boot is made to withstand the rain and also 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!





Tan Platform Chelsea Boots: Sorel Joan Now


Another cute and comfortable style, the Sorel Tan Chelsea Boots are a pleasant surprise by comfort brand Sorel. They’re waterproof, are slip-on, feature a sturdy rubber sole, and a stretchy opening that feels comfy on the ankles. 

Whether you’re planning to rock out at a music festival or just want some stylish sightseeing shoes, these boots are made for walking!


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!




Blundstone Unisex 550 Rugged Lux Chelsea Boot


Black Chelsea Boots for Outdoor: Blundstones 550


When asked about Blundstone boots for traveling, readers agree: these boots 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. Wearers like the comfort, quality and water resistance of the boots. They mention that they provide great ankle support, they mold to your feet and are waterproof. Available in many sizes both men and women. Buy it here!




FRYE Melissa Chelsea Boot


Gorgeous Genuine Black Leather Chelsea Boots: FRYE Melissa 


No boot article is complete without a pick from Frye Boots NYC, known for their beautiful genuine leather shoes. The Frye riding chelsea boot shown above is as timeless as it gets.

It’s important to note that this is not the traditional travel shoe that we normally recommend. It’s not known for its comfort and has no arch support, but if you’re looking for a quality investment piece, I can vouch that Frye leather boots can stand the test of time. I’ve had a pair for almost 20 years and the leather is still supple and has softened just the right amount over time.


Please note that these boots DO NOT have arch support and the sole is not rubber so they are best for non-slippery surfaces and for travelers without foot issues. Use anti-slip shoe pads for boots with wooden, not rubber soles!




Sam Edelman Tinsley Rain Boot


Easy-to-pack Chelsea Rainboots: Sam Edelman Tinsley


Rain boots are too bulky to pack in a carry-on but if you’re headed to a rainy and muddy location, these are your best bet to pack light.

The Sam Edelman Tinsley Rain Boot has a low 1-inch heel and a lightly padded lining to keep you warm for those rainy outdoor walking tours.

However, if you’re looking for a boot that will be comfortable enough for long hours sightseeing, we recommend these cute, comfortable, and waterproof leather boots instead.


For more ideas, take a look at these ankle-length rain boots!



Chelsea Boots Comparison Chart


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How to Choose the Best Womens Chelsea Boots




My airport outfit with chelsea boots (similar), jeans, blouse, and 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 admittedly we see a bit more variety these days.

This Chelsea boot is borrowed from the guys, bringing a masculine element to your wardrobe. Traditionally, it has a leather upper with a latex sole and tiny little heel to dress it up a bit. 

One of the most distinguishing features is that it’s a pull-on style boot. Sometimes it has a zipper, but usually, it has stretchy side panels that allow you to pull them on and off easily.

They can be a really handy boot 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 chelsea 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 is 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:






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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.