The Best Women’s Chelsea Boots

Asgard Women’s Ankle Rain Boots Waterproof Chelsea Boots

Classic Chelsea Boots That Are Also Waterproof

This versatile pair of shoes can be worn rain or shine.

Best Overall

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This simple and sophisticated pair of boots goes with any outfit. The rounded toe and simple design allow you to transition from day to night, while the rubber upper and rubber sole ensure that you can wear them no matter the weather. The side features elastic goring and a pull-tab at the heel so that you can easily put them on and take them off, and the toe area has extra space for added comfort along with an EVA insole to give you extra padding. Pair these boots with anything from a dress to jeans for a stylish and fashion-forward look that’s equally practical.

Pros:

• The rubber sole prevents slipping, even on wet surfaces
• The 5.5″ ankle shaft hits at the perfect height
• The lightweight style is made of rubber and is comfortable enough for all-day wear

Cons:

• The boots run large, so consider sizing down
• The rubber upper may rub your feet on the first few wears

DAWAN Women’s Anti-Slip Rain Boots

Safe, Secure, Stylish

This pair of boots is designed to make it easy to walk in any conditions.

Best Anti-Slip

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These boots are the answer to a more stylish approach to rain gear. The PVC upper looks like leather while being more durable for inclement conditions. The rubber sole is designed for optimal traction that mimics a tire pattern, helping you avoid slipping or sliding in rain, snow, or ice. And with a padded footbed and soft fabric lining, these shoes will keep your feet cozy and comfortable all day. Plus, the gore elastic at the sides makes it easier to slip them on and off for an all-purpose, functional, and stylish design.

Pros:

• The boots have an anti-slip tread on the bottom that will help you avoid slipping
• The PVC upper is waterproof to keep your feet warm and dry
• A padded footbed and fabric lining add comfort for long-term wear

Cons:

• The boots run a bit small, so it’s recommended to size up
• With frequent wear, the insole may come loose but can be replaced easily

PiePieBuy Women’s Tie Knot Chelsea Pump Ankle Boots

The Best of Both Worlds

These platform Chelsea boots have heels, so you can strut your stuff in comfort and style.

Best Heels

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These heeled boots can easily transition for any occasion. The fashionable suede style features an almond toe and wooden block heel for a trendy edge, while the subtle bow and sophisticated faux suede upper are timeless details. The interior of the boots features a cushioned insole to make it comfortable to wear all day, even with a heel. Plus, the side zipper closure makes it easy to throw these boots on quickly, making them perfect for your morning routine.

Pros:

• The 2.75″ heel is the perfect height to add sophistication, while still allowing for all-day walking
• The wooden block heel is a stylish and modern take on a classic Chelsea boot
• The boots have a side zipper to make it easy to put them on and take them off

Cons:

• Faux suede can get marked easily in rain, snow, or ice if not treated properly
• The bottoms don’t have a lot of treads, which can make them slippery in the rain

find. Women’s Leather Chunky Gumsole Chelsea Boots

A Timeless Look

This simple and timeless pair of boots will quickly become your daily go-to.

Best Leather

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These Chelsea boots are a true classic. The rounded toe and leather upper give them an edgy feel, while the chunky gumsole adds a fashion-forward touch. Better yet, the elastic inserts at the sides make the boots easy to slip on and off, and the ethylene-vinyl acetate sole gives you the grip you need to walk confidently, even in rain, snow, or ice. Pair these stylish boots with a dress for a tougher look, or add them to leggings and a sweater for a more casual approach to your style.

Pros:

• The leather upper will keep your feet dry in any weather conditions
• The elastic sides and pull-tab at the heel make them easy to slip on and off
• The 1″ sole gives you the tread you need for slippery conditions

Cons:

• The boots run in European sizing, so must be converted for those in the US
• The boots run narrow, so may not work well for those with wide feet

Dr. Martens Women’s 2976 Leonore Chelsea Boot

Faux Fur Lining to Keep You Warm

Even on the coldest days, this sherpa lining will keep your feet cozy.

Best Lined

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This classic leather Chelsea boot gets an upgrade with a few stylish details. The thick sole gives the boots a fashion-forward edge, while also adding extra tread for snow and ice. The sherpa lining keeps your feet and toes extra-warm, even on the coldest days. Plus, the upper and sole are heat-sealed and sewn together with a z-welt stitch for added security and protection to keep water and moisture out. Experience these heavy-duty boots for yourself and they’ll quickly become your cold-weather staple.

Pros:

• The sherpa lining is designed to keep your feet extra-warm, even in freezing weather
• The leather upper is fused to the sole through a heat seal and stitching for added protection against moisture
• The sole has good slip-resistance for slipper surfaces

Cons:

• Because of the thick lining, these boots run a bit small
• The boots are made of leather, so may take a few wears to break-in

Frequently Asked Questions

Are Chelsea boots waterproof?

Some Chelsea boot styles are designed to be waterproof, especially those with leather and rubber soles and uppers. However, not all styles are designed to withstand harsh weather. Be sure to check the specifics on the product listing to understand how they will hold up in rain or snow.

Can you wear Chelsea boots year-round?

Yes. Chelsea boots are a stylish footwear option at any time of the year. The short shaft, rounded toe, and variety of different available designs ensure that you can find ones to suit your personal style. Whether you choose leather, suede, or rubber, Chelsea boots are a versatile footwear option that can be styled for any occasion.

Do you tuck jeans into Chelsea boots?

No. Tucking your pant hem into your boots will visually shorten your silhouette. Instead, try cuffing the hem of your pants to create a sliver of ankle visible between the top of the boot and the end of your pant hem. This will help elongate your look and create a stylish finish for your outfit.

Are Chelsea boots good for snow?

Many Chelsea boot styles are great for the snowy seasons. Those with thick treads, leather or rubber uppers, and a comfortable lining are a great option for cold and wet days.