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Mild boot obsession? If your collection doesn’t include a pair of these slip-on boots, then you are sorely missing out. Fear not, we’ve got you covered with a compilation of the best Chelsea boots.
Table Of Contents
Shoe trends ebb and flow, and rarely do any stick around longer than a few seasons. The Chelsea boot is an exception. This cute boot style has become more than just a trend, ingraining itself as a full-on bootie obsession.
These boots have surpassed trend status, becoming a classic wardrobe staple. But this fashionable bootie is not only just a great shoe, but it happens to be the perfect shoe to bring on your travels! (Click here to learn how to create a capsule wardrobe with just three pairs of shoes!)
Ankle boots are some of the best boots for travel, especially if you’re headed to cooler weather or transition season climates. Keep reading for all the answers about these boots, but first, our readers offer their favorites.
Looking for more ankle boot suggestions? Here are our top picks!
What to Wear: Chelsea Boot
TFG Readers Pick: Teva De La Vina Dos Chelsea Boot
Best Chelsea Boots Readers’ Pick: Teva
For fashion-forward, casual Chelsea boots, then the Teva Women’s De La Vina Dos Chelsea boot is for you. It’s short, compact, casual, and cute.
If you’re looking for what to wear in London in May, the Teva is a great choice. While the weather is on the warmer side, the city does hit cooler spurts and sees a few days of rain — making this the perfect Chelsea boot to bring along.
TFG readers have a bootie obsession with these cute and casual brown leather boots. They’re ready for a sprinkle of rain with their waterproof material, a classy endeavour with their short heel, and an all-day walking tour with the soft canvas lining.
They’re lined and waterproof with rubber sole for stability, great if you’re looking for what to wear in Ireland on those rolling hills. These cute boots will compliment your fall adventures and make sure you’re looking cute as a button the whole way through. Plus, you can pick from four adorable but classic colors.
If you’re looking for an “AMAZING” (direct TFG reader quote) pair of Chelsea booties, then these are the pair for you!
We review the Teva De La Vina vs. the Ugg Simmens!
Best Chelsea Boot Editor’s Pick: Blondo
While we, too, love the TFG readers’ pick, the TFG editor’s pick is a sleek black Chelsea boot by Blondo.
These sleek black boots are 100% leather, with a flexible rubber sole, and heel that’s not too tall, but not too short, either. These booties are waterproof and easy to care for.
These leather Chelsea booties are very stylish and functional, and perfect for a trip to a snowy destination. They’ll keep your feet dry and warm. They are comfortable, functional, and, according to all reports, they fit great!
These booties are perfect if you’re looking for what to wear in Ireland in June. You’ll be comfortable walking and exploring all day!
These are the best shoes for Ireland!
Waterproof Chelsea Boots: Sam Edelman Tinsley
The easy pull-on style of the Chelsea boot makes it a favorite shape for rain boots. Compared to your traditional rain boot, the lower shaft and lighter weight of the Chelsea makes it a more packable boot for trips where you know waterproof shoes are a necessity.
The Sam Edelman Tinsley Rain Boot is the perfect example of a 100% rubber Chelsea boot, perfect for those wetter climates. These adorable boots have a low 1-inch heel, a comfy padded footbed, and cozy lining to keep you warm and comfortable for those rainy outdoor walking tours.
Add this boot your Irish fashion wardrobe for comfort and style!
While Hunter boots are the popular choice for rain footwear, they can get a little pricey. So if you’re looking for a similar-style boot that you can get on a budget, we’ve got some great choices for you.
Here’s our full round-up of the cutest ankle-length rain boots!
Budget Chelsea Boot: Joules Westbourne
If your shopping budget is tight this season or you’d rather save your hard-earned money for your trip, you’ll be happy to know that you can get a budget Chelsea boot.
Joules Westbourne Leather Boots are an affordable option to satisfy your bootie obsession. It’s the same chic look for less money, meaning you don’t have to sacrifice style by saving a few dollars.
I’m particularly fond of this pair of leather boots because it can be easily styled with any fall or winter outfit. It’s the perfect waterproof ankle boot with a feminine and sleek look that will compliment your outfit without giving away the discount price!
While it may not have the lifespan of some of the other higher-quality boots on this list, these babies should get you few you next one or two seasons. Plus it comes in a handful of colors, so you can really choose your style.
Looking for budget boots? We have a great round-up (if we do say so ourselves)!
Chelsea with Grip: Sorel
Chelseas come in all shapes, sizes, and grip strength. For a boot with a great grip, then the Sorel Lolla Bootie is your pick!
TFG readers love Sorel boots, which makes sense, considering the company’s well-structured brand and history of making warm, comfortable boots for cooler weather.
These leather boots have a synthetic sole with great grip — perfect for if you’re on your feet all day in the snow, ice, or simply cooler weather. They make for perfect fall or winter boots, considering the fabric liner built in for warmth, and the cushy moulded footbed, so you can walk all day!
While we’re raving about the functionality of these boots, we don’t want to forget the cute look. With a double buckle strap detail and full-grain leather finish, you couldn’t go wrong with the timeless look of these Lolla booties.
These boots are waterproof, with a canvas lining, allowing plenty of breathability and comfort for your feet. To look chic on a rainy day, then these are the Chelsea booties for you!
Looking for hiking boots or shoes? Learn how to pick the best!
Elegant Chelsea Boot: Geox
The versatility of the Chelsea boot style makes them the ideal boot for casual comfort or evening elegance. And if evening elegance is more your style, then who better to design your boot than well-known Italian brand Geox?
The Asheel Ankle Boot is a sexy, trendy, classic Chelsea boot with a sturdy and flexible stacked heel. The boots’ rubber sole is lightweight, breathable, and flexible, which is fantastic if you want to travel light.
These fashionable Chelsea booties are created with comfort in mind. They have a breathable and high-absorbing inner lining for an always-dry feeling. Whether you’re dressing for the streets of Milan or New York City, these waterproof Chelseas have you covered.
TFG readers love these cute booties, especially the side-entry zipper, which makes it easy to slide your travel boots on when you’re getting ready for a day of sightseeing.
These are the best shoes to pack for Italy!
Functional Chelsea Boot: Kodiak
One of the beauties of a good pair of boots is the exceptional functionality of them. Whether you’re out on the town exploring a new city, or running through the airport, these are the perfect travel boots for comfort.
If you’re looking for what to wear in London in June and want superior functionality, the Kodiak aims to design timeless and reliable boots, Canada’s version of Timberland boots. These cute, casual booties are great for your travels!
The classic design of the leather Alma Chelsea boot is perfect for all kinds of weather. The waterproof membrane construction with sealed seams and microfiber lining will keep your feet cozy and warm. And the removable leather memory foam insole offers maximum comfort and support, a feature that our readers rave about.
These Alma boots are cute and stylish, with slip-resistant rubber soles that absorb the shock of those cobbled streets in Norway. And they pair perfectly with a pair of jeans or a cute skirt.
Need more ideas for how to dress in London? Check out the TFG What to Pack For London e-book!
Comfortable Chelsea Boots: Dr. Martens
This is a more industrious Chelsea boot style that’s more fashion-forward and practical, making the Dr. Martens Flora Leather a perfect travel boot.
Dr. Martens are a much loved brand across the world for their famous air-cushioned sole. The Flora Chelsea boot, in particular, are awesome for adding a finishing edge to your travel outfit.
They are a great Chelsea style for travel because of their fashionable style, durability, and superior comfort. You can walk for miles in them over salty sidewalks, through snow and rain, and your feet will stay comfortable and warm, and the boots will retain their great look!
These boots are also vegan-friendly, so if you’re on the hunt for a responsible, fashion-friendly choice, then these are the Chelsea boot pick for you!
These are the best black ankle boots for sightseeing!
Chelsea Boot with Heel: Cole Haan
One of the great things about the variety-but-similarity of the Chelsea boot is that it has some standard features, like a heel that can be as tall or short as you want.
If you’re looking for some added height from your boots, then check out the Cole Haan bootie. These leather Chelsea booties have a stacked heel and looped pull, creating a classic stylish look that never goes out of fashion, and gives you a tad bit of height!
These high-quality boots are waterproof, perfect for a trek during a light rainy day in Wellington.
Or why not pair with cropped skinny jeans and a plaid shirt for a stylish outfit for a warmer vacation destination!
Suede Chelsea Boots: Rag & Bone
We admit, expensive doesn’t always mean better. But you can usually expect high quality construction and materials with a slightly pricier shoe. More expensive shoes also tend to have a better leather wear, and when you wear your boots down, you can typically get your boots repaired or resoled after extensive wear.
Shopping for an investment wardrobe piece can be a challenging activity — how do you decide? Which do you choose? Here at TFG, we recommend sticking to classic styles and colors when you’re investing (significantly) in your wardrobe and shy away from trendy designs and shapes.
If you’re looking for a great investment Chelsea boot, the Rag & Bone Walker Bootie has a waterproof coating without that rubber rainboot look, making them ideal for travel. These sleek Western-style Chelseas will stay on-trend for as long as they’ll last you (which will be a long time considering their high-quality make).
We round up the most comfortable shoes for travel!
Classic Chelsea Boots Women Love: FRYE
The traditional 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.
The FRYE Melissa boot is a great example of classic Chelsea style. Its shaft hits just above the ankle with a pull-tab on the back, and its streamlined construction compliments relaxed and contemporary outfits.
This Chelsea boot is borrowed from the guys, bringing a masculine element to your wardrobe. It’s got a leather top with a latex sole and tiny little heel to dress it up a bit. They match perfectly with a cute pair of jeans or a classic summer dress!
If you are looking for a boot to invest in or one that will stand the test of time, look no further than a classic Chelsea.
Not sure which clothes to wear with a pair of these brown Chelsea boots? Here’s how to wear ankle boots!
Best Chelsea Boots Womens Print: Sam Edelman Petty
Perhaps your Chelsea boo style comes with a little more flare and gravitas. Then a printed Chelsea boot might just be the perfect addition to your travel wardrobe.
Despite the bold print, a pair of patterned suede Chelsea boots like the Sam Edelman Petty Ankle Boot still maintains the versatility and comfort of the classic Chelsea boot style, but it provides gives oomph to your outfit.
Adding a print like this fabulous leopard style is a great way to play up its classic look. And they’re hearty enough to spend all day on your feet, perfect for your next trip to Rome! Note that the Sam Edelman boots like these have limited traction, so they’re not great for sleet, ice, or snow.
Make sure you bring more than one outfit that goes with these cute booties. If you stick with a neutral color like taupe or grey, it can easily be matched with many items in a capsule travel wardrobe!
Yes, you can wear prints on vacation! Read our tips!
Stylish Chelsea Boot: Marc Fisher Yente
You can’t go wrong with a little bling here and there! Add a little glitz and glam to your wardrobe by giving the classic Chelsea boot a few embellishments.
The Mark Fisher Yente Chelsea Boot is a boho-chic pair of Chelsea style boots. Not only does it have stand-out studs, but we absolutely love the scalloped stitching and gleaming toe tip.
Whether you’re planning a night out in Madrid or heading to a roaring music festival, these boots will be a stylish addition to your travel wardrobe.
Wondering what to pack for a music festival? Read this!
Brown Chelsea Boots: Marc Fisher Yale
Not everyone’s style of bold includes bling, and Chelsea boot styles come in all shapes, sizes, and colors, for the travel fashionista in all of us.
If you’re looking to add a tad bit of alternative style to your wardrobe but aren’t looking for flashy and bling, then the Marc Fisher Yale boot will help you play up simple jeans and white tee combo with this unexpectedly bold Chelsea boot.
A touch of texture can instantly elevate a boot. The texture on these boots almost creates the look for a print without actually being one — making them blend seamlessly into any outfit. And we love it!
Chelsea Boots Comparison Chart
|BRAND / MODEL||REVIEWS||RATING||PRICE|
|Teva De La Vina Dos Chelsea Boot||For fashion-forward, casual Chelsea boots, then the Teva Women’s De La Vina Dos Chelsea boot is for you. It’s short, compact, casual, and cute.||Check Price|
|Blondo Elvina Waterproof Ankle Bootie||These sleek black boots are 100% leather, with a flexible rubber sole, and heel that’s not too tall, but not too short, either. These booties are waterproof and easy to care for.||Check Price|
|Sam Edelman Tinsley Rain Boot||The Sam Edelman Tinsley Rain Boot is the perfect example of a 100% rubber Chelsea boot, perfect for those wetter climates.||Check Price|
|Joules Westbourne Leather Chelsea Boot||Joules Westbourne Leather Boots are an affordable option to satisfy your bootie obsession. It’s the same chic look for less money, meaning you don’t have to sacrifice style by saving a few dollars.||Check Price|
|Sorel Lolla Bootie||These leather boots have a synthetic sole with great grip — perfect for if you’re on your feet all day in the snow, ice, or simply cooler weather.||Check Price|
|Geox Asheel Ankle Boot||These fashionable Chelsea booties are created with comfort in mind. They have a breathable and high-absorbing inner lining for an always-dry feeling.||Check Price|
|Kodiak Alma Chelsea Boot||The classic design of the leather Alma Chelsea boot is perfect for all kinds of weather. The waterproof membrane construction with sealed seams and microfiber lining will keep your feet cozy and warm.||Check Price|
|Dr. Martens Flora Chelsea Boots||This is a great Chelsea style for travel because of their fashionable style, durability, and superior comfort. You can walk for miles in them over salty sidewalks, through snow and rain, and your feet will stay comfortable and warm, and the boots will retain their great look!||Check Price|
|Cole Haan Newburg Boot||These leather Chelsea booties have a stacked heel and looped pull, creating a classic stylish look that never goes out of fashion, and gives you a tad bit of height!||Check Price|
|Rag & Bone Walker Bootie||The Rag & Bone Walker Bootie has a waterproof coating without that rubber rainboot look, making them ideal for travel. These sleek Western-style Chelseas will stay on-trend for as long as they’ll last you (which will be a long time considering their high-quality make).||Check Price|
|FRYE Melissa Chelsea Boot||The FRYE Melissa boot is a great example of classic Chelsea style. Its shaft hits just above the ankle with a pull-tab on the back, and its streamlined construction compliments relaxed and contemporary outfits.||Check Price|
|Sam Edelman Petty Ankle Boot||Sam Edelman Petty Ankle Boot still maintains the versatility and comfort of the classic Chelsea boot style, but it provides gives oomph to your outfit.||Check Price|
|Marc Fisher Yente Chelsea Boot||The Mark Fisher Yente Chelsea Boot is a boho-chic pair of Chelsea style boots. Not only does it have stand-out studs, but we absolutely love the scalloped stitching and gleaming toe tip.||Check Price|
|Marc Fisher Yale Chelsea Boot||The texture on these boots almost create the look for a print without actually being one — making them blend seamlessly into any outfit.||Check Price|
What are Chelsea Boots?
The Chelsea is a type of ankle boot that’s simple but stylish, comfy, and versatile, making it a great addition to most packing lists. It’s a pull-on style boot. Sometimes it has a zipper, but usually it has a 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 you need to slip your shoes on and off easily. If you’re wondering about wearing your boots on a plane, our readers offer their advice!
Some boots are even small enough to fit into a slim packing cube instead of a shoe bag!
How to Wear Chelsea Boots?
Chelsea booties are a great addition to any travel outfit. You can wear them with jeans, a dress, or even a cute skirt! The best thing about them is that you can wear them with pretty much anything!
What Shoes Should I Pack for Travel?
Need more general insights on packing shoes for travel? Start by reading our best tips and tricks on choosing the best shoes for travel:
- 10 Steps to Packing the Best Travel Shoes
- The Importance of Packing the Best Shoes for Travel
- Don’t Break these Travel Shoe Rules
What do you think are the best Chelsea boots for travel? Please share your comments below!
For more tips on travel boots, please read:
- Best Ankle Boots for Fall
- Ankle Booties – The Best Travel Shoes for Europe
- Budget-Friendly Autumn/Winter Boots
- Best Ankle Boots for Travel to Europe
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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.