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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
Table Of Contents
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!
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!
Read our review of the Teva De La Vina vs. the Ugg Simmens boot!
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!
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!
Stylish Suede Chelsea Boots: Cole Haan
We are in love with the Cole Haan 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!
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. Now available in their new version, Sorel Emelie II and Sorel Emelie III!
While knee high boots and ankle booties are forever classics, our readers are loving these mid-calf 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 Cate
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!
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!
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
|BRAND | MODEL||FEATURES | REVIEWS||RATING | PRICE|
|Kenneth Cole Salt Chelsea Boot||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.||Check Price|
|Teva Anaya Chelsea Boot||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.||Check Price|
|Dr. Martens Flora Chelsea Boots||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.||Check Price|
|Blondo Dagger Waterproof Ankle Boots||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.||Check Price|
|Cole Haan Chelsea boot||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.||Check Price|
|Sorel Emelie Waterproof Bootie||Travelers love Sorel boots especially for wet, snowy, cold, and extreme winter weather.||Check Price|
|Born Cove Chelsea Boot||Born brand is a long time reader favorite and their Cove chelsea suede boot is sure to become one of their newest must haves.||Check Price|
|Sorel Cate Chelsea boot||Whether you’re planning to rock out at a music festival or just want some stylish sightseeing shoes, these boots are made for walking!||Check Price|
|FRYE Melissa Chelsea Boot||No boot article is complete without a pick from Frye Boots NYC, known for their beautiful genuine leather shoes. The Frye riding chelsea boot is as timeless as it gets.||Check Price|
|Sam Edelman Tinsley Rain Boot||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.||Check Price|
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:
- 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.