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Very few boot styles have stood the test of time, unlike the Chelsea boot. Trends may come and go, but this fall/winter necessity continues to transcend each one of them. Thanks to their practical design and durable construction, Chelsea boots can be worn season after season.
Not to mention, the style has been around forever – since the Victorian Era, to exact. The Chelsea boot was actually created by Queen Victoria’s shoemaker J.Sparkes Hall, who designed it for her to wear around her castle and while riding her many horses.
The name of the Chelsea boot has an equally posh origin, hailing from London’s affluent Chelsea neighbourhood that’s known for its high-end boutiques and restaurants.
The style gained popularity in the 60s when it was worn by the Beatles and the Rolling Stones, and it’s remained a staple in the closets of many. That’s why we’ve rounded up the best womens Chelsea boots for you to shop.
How to Choose The Best Women’s Chelsea Boots
The defining features of the Chelsea boot are the ankle-length and elasticated side panels, which add to its versatility, comfortability, and simple design. When you pull on a pair of Chelsea boots, you look effortlessly fashionable.
So, if you have no boots, need a new pair of basic boots, or have 500 pairs, it doesn’t matter – Chelsea boots make a great addition to your wardrobe for everyday wear. That said, there are a few things to consider when choosing the best pair for you, like price point, material, brand, and occasion.
Brand
Almost every shoe brand has produced its take on the Chelsea boot, but luckily for you, we did all of the research on the most popular brands so that you don’t have to. Blundstone, UGG, Hunter, Dr. Martens, Timberland, and Aldo are all known for creating high-quality Chelsea boots, while other brands such as Madewell and Rag & Bone provide a different take on the style.
The most classic options are delivered by Clarks and more modern styles come from Vagabond and Marc Fisher Footwear. Regardless of the brand, there are a pair of Chelsea boots out there that you’re bound to fall in love with.
Material
Chelsea boots come in a range of materials including leather, suede and even vegan leather, if you prefer not to purchase boots made with animal products. However, if you are ok with a leather such as calfskin, it’s a great option for Chelsea boots because it creates an unbelievably sleek look.
Overall, your choice of material when it comes to Chelsea boots is key not just when it comes to style points, but functionality too. If you’re planning on wearing your boots in all weather conditions, then it’s necessary to consider a water-resistant or waterproof pair.
Price
Since your budget will also determine the quality of the Chelsea boots that you buy, we made sure to include pairs at all price points to give you the best options available. The cost of the boots included in this list are also a reflection of the brand names, with Rag & Bone at the high-end of the spectrum and Aldo at the low-end.
- Dr. Martens Flora Smooth Leather Womens Chelsea Boots, $150
- Nisolo Classic Womens Chelsea Boots, $185
- Timberland Courmayeur Valley Womens Chelsea Boots, $150
- Madewell The Ainsley Womens Chelsea Boots, $198
- Thursday Boots Duchess Womens Chelsea Boots, $160
- Marc Fisher Yale Pointy Toe Womens Chelsea Boots, $179
- Rag & Bone Rover Boot, $395
- J.Crew Blundstone Original 500 Womens Chelsea Boots, $189.95
- Vagabond Kenova Womens Chelsea Boots, $140
- Clarks Clarkdale Arlo Womens Chelsea Boots, $200
- Hunter Refined Stitch Detail Womens Chelsea Boots, $175
- UGG Markstrum Chelsea Boots, $150
- Aldo Larecaja Chelsea Boots, $79.98
12 Best Womens Chelsea Boots
Whether you are looking for a timeless pair of plain black leather boots or a timeless brown suede pair, we’ve got you covered. No matter where you plan to go or how you plan to wear these Chelsea boots, they’ll always be up for the occasion.
Durable, comfortable, stylish, and extremely versatile, Chelsea boots have a clean, refined look that is never overdone. Here are the 12 best pairs of women’s Chelsea boots to shop right now:
#1 – Dr. Martens Flora Smooth Leather Women’s Chelsea Boots
Dr. Martens is widely known for its selection of punky, grungy boots. The British footwear brand has taken the globe by storm for decades, stealing the hearts of everyone from musicians to preppy fashionistas to celebrities, and the Flora Smooth Leather Women’s Chelsea Boots are the best choice if you’re looking for a name brand without a price tag to match.
These boots have a low, no skid air-cushioned sole that makes them perfect for any weather. The low profile silhouette and smooth polished leather adds a slick, feminine flair to any outfit as well. Available in black in sizes 5 to 11, they ring in at $150. Plus, anyone who owns a pair of docs knows that they get better with age, becoming more comfortable after every wear.
#2 – Nisolo Classic Women’s Chelsea Boots
We love a sustainable brand and Nisolo ranks at the top of our list. The company makes all of its products ethically and all of its producers receive wages that are well beyond fair trade. Available in sizes 5 through 11, the Nisolo Classic Womens Chelsea Boots are ideal for daily wear, but they can also be dressed up at night for.
Although these Chelsea boots are conveniently made with water-resistant material, what makes them unique is their triangular elastic side panel. The shape is extremely flattering because it makes your legs look longer, and who wouldn’t want that? They also come in four colourways (black with a brown heel, black on black, brown, and brandy), and they’re currently on sale for $185 from $200.
The only downside to purchasing these boots is that the brand only ships within the United States at this time, which we are hoping they change soon!
#3 – Timberland Courmayeur Valley Women’s Chelsea Boots
Timberland is known for making high-quality work boots that look just as good with streetwear, and a combination of these two things was made popular by hip-hop artists in the late 90s and 2000s. The company’s pro line can even be worn to do construction work, while other styles like the Courmayeur Valley Women’s Chelsea Boots have become a fall/winter closet staple.
Though these ‘Timbs’ are not made in the brand’s traditional style, they compliment casual ensembles with their heavy lug outsoles and topstitching. They also come with ortholite insoles, which provide extra padding for your feet. Ringing in at $150, they come in sizes 5.5 to 11 and three neutral colours: grey nubuck, black nubuck, and dark brown nubuck.
#4 – Madewell The Ainsley Women’s Chelsea Boots
When you think of Madewell you probably think about jeans, but did you know that the brand also makes a killer pair of Chelsea boots? The Ainsley Women’s Chelsea Boots are made from soft and supple leather that stretches overtime for a more comfortable wear, in true black and ‘English saddle’.
To top things off, Madewell’s signature MWL Cloudlift Lite padding provides extra cushion for your feet, so you’ll be walking on clouds in no time. If you are looking for a simple and polished pair of Chelsea boots to carry you through the coldest seasons, you can scoop these up in sizes five to 11 for $198.
#5 – Thursday Boots Duchess Women’s Chelsea Boots
If you are looking to shop a brand that focuses on quality and affordable pricing, Thursday Boots is it. This small company sells handcrafted shoes and focuses on ethical sourcing, responsible manufacturing, fair labour, and sustainability. They also know how to pay homage to a heritage style like the Chelsea boot with the Duchess Women’s Chelsea Boots.
These booties come in dark olive, brown, shadow grey, ash, glazed ginger, and cognac-coloured suede, as well as black, old English, black coffee, brown, and toffee-coloured leather. With a durable rubber base and outsole, they come in sizes 5 through 11 and are priced at $160.
#6 – Marc Fisher Yale Pointy Toe Women’s Chelsea Boots
Marc Fisher Footwear was founded by the son of Jerome Fisher, who is the co-founder of Nine West. So, designing shoes is in his blood, and Marc nailed the design of the Yale Pointy Toe Womens Chelsea Boots: a modern yet timeless shoe that feels luxurious on the foot.
Made for both fashion and function, this style of boot elongates the foot, and the thin metal details on the toes will catch the eyes of everyone you walk by. Available in sizes 5 through 12, these boots come in a large range of fabrics and colors, from black or ivory leather to taupe and brown suede for $179.
#7 – Rag & Bone Rover Boot
Rag and Bone’s edgy jeans and footwear have become popular amongst celebrities and Victoria Secret models. And yes, we would buy these boots just to copy Candice Swanepoel. The Rover Boot features an almond-shaped toe and an exaggerated heel for a little added height.
With an anti-slip outsole that’s wearable throughout the seasons and a large size range from 35 to 41 (EU), they’ll quickly become one of the most reached for pairs in your closet. With a price tag of $395, they’re a bit more expensive, but are worth the investment if you wear them everyday.
#8 – Blundstone Original 500 Women’s Chelsea Boots
Blundstone is a family-owned business that has been around since the mid-1800s. Today, the Tasmanian boot brand is one of the most recognized for their weatherproof, gender-neutral Chelsea boots, including the best-selling Original 500s.
Designed in 1969, these rugged pull-on Chelsea boots will always be in style. Shaped to the foot for comfort and designed to withstand any kind of weather, they’re water-resistant, lightweight, and make the perfect addition to any outfit. Available in size 5 through 12 and colours like voltan black and stout brown, the Original 500 Women’s Chelsea Boots ring in at $189.95.
#9 – Vagabond Kenova Women’s Chelsea Boots
Vagabond may not be the most well-known shoe brand featured, but it is one of the leading brands of affordable shoes in Europe. It is true, European women do dress the best, so why not take a page out of their book? You can start with the effortlessly chic Kenova Women’s Chelsea Boots.
These black, round-toe booties feature a chunkier outsole and a 40mm heel, which gives them a youthful and trendy look. Priced at $140, they feel like a steal but Vagabond tells you exactly where they’re made and where the materials were sourced to make them. Plus, they come in an expansive size range from 35 to 42 (EU).
#10 – Clarks Clarkdale Arlo Women’s Chelsea Boots
Clarks is another British footwear company that has stood the test of time thanks to their high-quality, reasonably priced products. Although the brand was founded in 1825, its perennial styles – like the infamous Desert Boot – are still trending today, including the Clarkdale Arlo Women’s Chelsea Boots, which ring in at $200.
To provide you with a little extra comfort, these Chelsea boots are available in a medium or wide width depending on your needs, and in sizes 5 through 10 in either medium or wide width depending on your needs. They also come in five different patterns, colours and materials including pebble suede and leopard print.
#11 – Hunter Refined Stitch Detail Women’s Chelsea Boots
Need rain boots? Look no further than Hunter – for Chelsea boots too! The Refined Stitch Detail Women’s Chelsea Boots are functional and stylish with a pronounced outsole platform and chunky heel for grip and support.
Whether you’re constantly running around the city or planning a weekend getaway to the countryside, these 100 per cent vegan boots are the only thing you need to pack for footwear. They’re entirely waterproof and come in sizes 5 through 11. Whether you choose a plain black pair or you go slightly lighter with ‘grey heron’, they’ll cost you a slim $175. Bonus: they come with a two-year warranty!
#12 – UGG Women’s Markstrum Boot
UGG may be known for its fuzzy, winterized mules and adorable furry slippers, but the Australian footwear giant makes a wide variety of shoes, including the Markstrum Boot. The chunky Chelsea boots of your dream, they come in a sharp, matte black waterproof leather in size 5 through 12.
These are the booties to wear in even the most torrential weather, from rain to light snow. At $150, their edgy, slightly punky look is streamlined enough to be dressed up for a work or a dinner date. And if you can’t decide between a pair of trendy lug sole boots or classic Chelsea’s, this style is the perfect crossover.
How should you wear Chelsea boots?
If you want a pair of boots that do the styling work for you, then Chelsea boots are the way to go. Whether you enjoy dressing in boho, ultra-casual, elegant or super trendy clothing, there’s a pair of Chelsea boots to match your style.
Pairing them with denim jeans, a sweater, a jacket, and a scarf for the ultimate fall or winter ensemble. If you want to spice things up, throw a printed coat or a blazer over top. From Julia Roberts to Alexa Chung, we’ve seen a similar look on nearly every celebrity there is, but regardless of how you wear your Chelsea boots, they’ll have you looking put together in no time.
What are the most comfortable Chelsea boots for women?
Chelsea boots are known for being extremely practical, wearable, and most importantly, comfortable. The following brands focus on comfort:
- Dr. Martens Flora Smooth Leather Women’s Chelsea Boots
- Timberland Courmayeur Valley Women’s Chelsea Boots
- Madewell Ainsley Women’s Chelsea Boots
- Hunter Refined Stitch Detail Women’s Chelsea Boots
- Thursday Boots Duchess Women’s Chelsea Boots
When buying any pair of boots, it’s important to focus on the small details like high-performance and shock-absorbing insoles, as well as stretchy, elastic fabrics that move with you so you never have to worry about blisters again.
How do you clean women’s Chelsea boots?
Lived-in boots look great, but once they pass the point of looking cool it’s time to clean them up. If your boots are not waterproof, try not to get them overly wet. Be sure to apply a leather protector and remove excess dirt with a soft brush on either suede or leather.
To clean your suede Chelsea boots:
- Stuff them with a paper towel or newspaper
- Use a suede cleaning brush to get rid of stains and mud
- Rub them with a towel to dry
To clean your leather Chelsea boots:
- Shake off excess dirt with a shoe brush
- Use a damp cloth to wipe off any extra debris
- Use a soft brush to put on leather cleaner and polish marks off
For extra tough stains, you can buy a stain cleaner or use white wine vinegar. Keeping your boots clean means they will last longer, so it’s worth the extra work!
Which Chelsea boots are the best?
If you’re wondering which Chelsea Boots are the best choice for you, refer to the quick facts below:
Top affordable Chelsea Boots (from least expensive to most):
- Vagabond Kenova Womens Chelsea Boots, $140
- Dr. Martens Flora Smooth Leather Womens Chelsea Boots, Timberland Courmayeur Valley Womens Chelsea Boots, UGG, $150
Top 3 luxury Chelsea Boots (from least expensive to most):
- Madewell The Ainsley Womens Chelsea Boots, $198
- Clarks Clarkdale Arlo Womens Chelsea Boots, $200
- Rag & Bone, $395
Top 3 Chelsea boots to shop for the best value (from least expensive to most):
- Vagabond Kenova Womens Chelsea Boots, $140
- Dr. Martens Flora Smooth Leather Womens Chelsea Boots, $150
- Thursday Boots Duchess Womens Chelsea Boots, $160
All in all, investing in the best pair of Chelsea boots for you really depends on your needs, but no matter which pair you buy, you can be confident knowing they’ll never go out of style.
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