Fashion » 17 Coolest Women’s Chelsea Boots to Buy: Chelsea Boots Styling Guide

17 Coolest Women’s Chelsea Boots to Buy: Chelsea Boots Styling Guide

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Many women love Chelsea boots for their versatility and comfy look and feel. Chelsea boots have a round toe and flat sole, usually with a minor heel. They rise to or slightly above the ankle, so you most likely already wear them with skinny jeans or leggings. They’re simple and elegant, but they come in a variety of styles so you can make them work with nearly any outfit.

Coolest Women's Chelsea Boots to Buy
@fashion_jackson, @bartabacmode

Still not sure how to make a Chelsea boot look right with your wardrobe? Check out these 17 coolest women’s Chelsea boots to buy and read our styling guide below, so you know how to wear each pair. When you’ve caught up on styling your boots, you’ll want to make up an excuse just to get out of the house and show them off.

Women’s Guide to Chelsea Boots: Contents

17 Best Women’s Chelsea Boots to Consider Getting

You think you might like the idea of wearing Chelsea boots, but you’re not sure where to start. Take a look at these 17 pairs of Chelsea boot styles to decide which are right for you. Once you learn about what makes each pair different, you’ll know which features will work best with your typical outfits.

1. Classic Leather Chelsea Boots

Sometimes it’s best to start with the most classic version of a popular shoe. Common Projects’ black leather Chelsea boots are the best you’ll find. Each pair features genuine Italian leather and a tan lining. Make sure to look for the brand’s signature golden serial number just above the heel, available at Net-a-Porter.

Best Women's Chelsea Boots: Common Projects Chelsea Boots

2. Church’s Ketsby Leather Boots

When you want shoes made by one of the oldest brands in the business, look no further than Church’s Ketsby Chelsea boots. The brand uses a glossy leather that gives them a gorgeous shine. The studs that form a wingtip above the rounded toes are another sparkly element to make this shoe stand out from your wardrobe. They’re available for sale at My Theresa.

Best Women's Chelsea Boots: Church's Ketsby Chelsea Boots

3. “Petty” Minimalist Chelsea Boots

Anyone who wants to become minimalist or already lives that lifestyle will adore the “Petty” Chelsea boot style. They’ve got a low heel and cut, plus a side zipper for a seamless appearance. Another minimalist bonus – you can use them year-round, so you don’t need to waste space with extra shoe storage in your home. If you want to try them on, you can find them at Nordstrom in two colors.

Best Women's Chelsea Boots: Sam Edelman Chelsea Boots

4. Gold Eyelet Tall Boots

Looking for a statement shoe? Look no further than these gold eyelet Chelsea boots by See by Chloe. They have a modest one-inch heel but rise a couple of inches past the ankle. Antique gold eyelets line the elastic siding, while the rest of the shoe is calfskin leather. Curious shoppers can buy these beauties at Revolve in several sizes.

Best Women's Chelsea Boots: See by Chloe Helen Chelsea Boots

5. Pointed-Toe Heeled Chelsea Boots

Cowgirl boots are a popular accessory, but they don’t go with every outfit. When you need something a bit shorter, try the Reike Nen pointed Chelsea boots. Made with brilliant white leather and intricate stitching, they mimic classic country boots. The pointed three-inch heel and toe define any look. You can find them at Forward.

Best Women's Chelsea Boots: Reike Nen Chelsea Boots

6. Stud Embellished Santoni Boots

Grunge is coming back in a big way, and if you vibe with the trend, you’ll want Santoni’s Chelsea boots for women. They have the classic leather look with elastic sides, but with silver studs over the toes and around the heel. Pair them with dark gray stonewashed jeans for a modern grunge outfit. These boots are available online at Farfetch.

Best Women's Chelsea Boots: Santoni Chelsea Boots

7. Alexander Wang Cutout Chelsea Boots

Shoes are supposed to catch people’s eyes as you walk past, which is what will happen when you wear Alexander Wang’s cutout Chelsea boots for women. They take after the classic leather look but change it in a few ways. These boots rise above the ankle and make a bold statement with cutout wedges on the back of the heel. Try them on when you order from Net-a-Porter.

Best Women's Chelsea Boots: Alexander Wang Andee Chelsea Boots

8. Isabel Marant Chelay Leather Boots

Some outfits require boots that are a bit higher than your ankle but don’t rise past your calves. If you’re looking for a pair like this, you’ll love the Isabel Marant Chelsea boots. They model the Chelsea style with a short heel and almond toes, but the brand designed the shoe with calf leather from Portugal to rise just past the hemline of your jeans. Try them on after checking them out at My Theresa.

Best Women's Chelsea Boots: Isabel Marant Chelay Chelsea Boots

9. Block Chunky Heel Boots

If you’re a fashionista who lives for big heels, try out the Tony Bianco Chelsea boots for women. These black leather boots feature a chunky 2.5-inch heel and elastic straps on the front and back of the shoe. It’s the perfect blend of classic and cool, which you can pick up at Revolve.

Best Women's Chelsea Boots: Tony Bianco Hampton Chelsea Boots

10. Saint Laurent West Chelsea Boots

On those nights where you want to wear something that goes all out, slip into these Saint Laurent Chelsea boots. These boots come in Italian suede and have a leather sole, plus parallel stitching that complements the fine lines of the boot. You won’t be able to resist this vintage look and leaning heel, available at Forward.

Best Women's Chelsea Boots: Saint Laurent West Chelsea Boots

11. Dr. Martens Chelsea Boots

Not ready to leave your Doc Martens behind? You don’t have to when you wear the Flora Chelsea boots. They have the signature Dr. Martens tag on the back but Chelsea style, with dyed haircalf covering the boots in a classy leopard print. You’ll want to wear these slip-resistant boots every day after you find them at Shopbop.

Best Women's Chelsea Boots: Dr. Martens Flora Hair on Chelsea Boots

12. Refined Glossy Chelsea Boots

Another popular way to wear Chelsea boots with style is to get them glossed up. They’ll shine in the sun and last in any heavy downpour because you bought them from the renowned Hunter brand. Wear these stylish boots all year long with jeans or shorts. They’re available for sale online at Revolve.

Best Women's Chelsea Boots: Hunter Original Refined Chelsea Boots

13. Dolce & Gabbana Embellished-Heel Boots

Marry your love of studded shoes and Chelsea boots with these Dolce & Gabbana embellished heels. They take on the original Chelsea style and create pointed elastic siding to complement the almond toes. The focal points of these Chelsea boots for women are the embellished heels, which have pyramids made of gunmetal and the brand’s logo embedded in studs. You can check them out at Farfetch.

Best Women's Chelsea Boots: Dolce & Gabbana Chelsea Boots

14. Italian Suede Chelsea Boots

Those who want to venture into a new style without jumping too far from what they already love will adore these Rag & Bone suede Chelsea boots. The classy stacked block heel molds beautifully to the suede boots and elastic panels. They’re what you want to wear with a deep blue pair of jeans and a chunky sweater. Anyone wanting something cozy and cute can find them at Net-a-Porter.

Best Women's Chelsea Boots: Rag & Bone Walker Chelsea Boots

15. Elegant Pointed-Toe Chelsea Boots

People hunt for a smart and sophisticated style for dinner parties and dates, and you’ll find it in these Marc Fisher Chelsea boots. The pointed toe and triangular elastic paneling line up perfectly with the short heel. Genuine leather completes the sophisticated look, available at Nordstrom in different colors and textures.

Best Women's Chelsea Boots: Marc Fisher LTD Yale Chelsea Boots

16. Rubber Sole Chelsea Boots

You can get Chelsea boots made with Italian leather and a uniquely layered look when you try on the 100% leather Paloma Barceló shoes. The elasticated side paneling and rear pull tab fit naturally into the design of the boot. The rubber sole is what makes the statement, layering black and brown stripes for a wood-paneling effect. They’re currently available at Farfetch.

Best Women's Chelsea Boots: Paloma Barcelo Chelsea Boots

17. Chunky Chelsea Boots

Looking for a stylish boot to wear in the countryside? You’ll want to bring the See by Chloé Chelsea boots along with you. They stand out from their competition because of their taupe suede and rubber soles with deep grooves for off-trail traction. The elastic siding reaches from top to sole, so you can easily slip them on and off. Interested fashionistas can check them out at Net-a-Porter.

Best Women's Chelsea Boots: See by Chloe Suede Chelsea Boots

What Are Chelsea Boots, and What’s Their History?

Originating from Chelsea, England in the 1950s-1960s, Chelsea boots are close-fitting ankle boots, usually with a small heel and an elastic side panel that makes slipping into them a breeze. There are many style varieties with Chelsea boots, so it may seem like they’re a modern invention.

It may surprise some people to discover that they’ve existed since 1851 when the Chelsea Boot Company began. At the request of Queen Victoria, J. Sparkes-Hall created a short boot with elastic siding, so she didn’t have to worry about her laces getting stuck in her stirrups while she rode on horseback.

In the 1960s, the Beatles popularized the style again by requesting boots with a Cuban heel. You will sometimes still see it called “the Beatle boot” for this very reason.

What Are Chelsea Boots, and What's Their History?

Today, both men and women wear Chelsea boots in hundreds of different styles. They’re easily adaptable to various fashion trends and remain a crowd favorite when it comes to dependable footwear.

How to Wear Chelsea Boots for Any Occasion

Picking out the perfect shoes for every outfit can make or break your look of the day. Casual sandals with an evening gown would never go together as well as a classy pair of heels with the same dress. If you’re going to put together a look that makes a statement, you’ll need to know all about the kinds of shoes you prefer.

Now that you’ve seen some of the trendiest Chelsea boot styles and know about their history, it’s time to learn how to wear them for any occasion.

Try an Everyday Casual Style

The first thing you should know is how to match your new favorite pair of Chelsea boots to your everyday style. They work well with cuffed jeans and a T-shirt, as well as camel coats and leather jackets. You might style them with a scarf or a tweed coat, along with a wide-brimmed hat or beanie.

Many people add leggings or tights to wear their favorite Chelsea boots all year long. If you play around with different textures and colors, you can wear Chelsea boots with any daily style you prefer.

When wearing Chelsea boots with jeans, leggings, and pants, make sure to let the hem stop before your ankle to prevent a bulky look. You can also style them with skinny jeans tucked into the booties for a leg elongating effect.

Avoid combining your Chelsea boots with long pants covering them and showing only the toe, as this will make you look shorter and bulkier.

Chelsea Boots Outfits Ideas

Wear Them Business Casual

Depending on your workplace, you can wear Chelsea boots for a business casual dress code in a couple of different ways. You might pair a classic style with tights and a bold-print dress. Match ankle Chelsea boots with a long pencil skirt and blazer or style them with a top coat for a complete accessorized look.

Pick Chelsea boots with pointed toes, skinny heels, and neutral colors to help them fit in with your office. They’ll also complement skinny or wide-leg trousers if skirts and dresses aren’t your style.

Hit the Clubs

Chelsea boots are so comfy and chic, they’re the perfect shoe to wear on your night out. After you find the right after-dark dress, pair it with high-heeled Chelsea boots or shoes in a bright color. They’ll add a bit of grunge to make your outfit edgy.

Play around with colors and styles by layering your tight dress with a loose leather jacket and dark pair of Chelsea boots for a look that says you’re ready to have fun.

Dress Them up

Easily dress up any outfit when you slip into a pair of Chelsea boots. A tight skirt or a flared-out style goes great with a pair of classic leather Chelsea boots. Aim for a higher heel or lower boot height to match them with a fancy dress and a pair of tights.

How to Wear Chelsea Boots for Any Occasion

Abide by Basic Dos and Don’ts

While you decide which kinds of Chelsea boots will work with the outfits in your wardrobe, remember these fundamentals to set you on the right path to fashion success.

Always try to:

• Adjust your heel to your outfit

• Incorporate new textures

• Wear Chelsea boots with the right weather

Never wear Chelsea boots with:

• Capris

• Cropped tights

• Cropped pants

Play Around with Them

Playing around with different outfits is the best thing you can do to get used to styling Chelsea boots. Order a few pairs that catch your eye and dress up in different clothes in front of your mirror. You’ll quickly get the hang of which outfits go with different colors and textures, so you’ll rock your Chelsea boots anytime, anywhere.

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