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Chelsea boots are a timeless shoe for any wardrobe — here's how to wear them

Stylists prove that these boots are more than just a seasonal staple.
Vivian Le / Kara Birnbaum / TODAY

While other fall fashion trends come and go, the Chelsea boot is a tried-and-true style that is equally functional and fashionable. Over the years, this wardrobe staple has been paired with jeans, slacks and leggings and is one of those shoes that still manages to elevate any fall attire.

“Chelsea boots are a footwear staple,” says New York City-based personal stylist Gloria Cospito. “This season, Chelsea boots are getting a streetwear upgrade with higher shafts and chunky soles.”

With updated takes and new iterations, Celebrity fashion stylist Kim Appelt says the lug sole trend is on its last legs this fall, but the style is still kicking around. 

“We see brands coming out with new versions of the lug sole and also sleeker silhouettes,” she says. “It’s safe to say we are in a transition and if you love a heavy sole, definitely still make that purchase.”

Read below to see what experts recommend and how you can upgrade your fall footwear repertoire.

How to style Chelsea boots | Are Chelsea boots timeless? | Are Chelsea boots comfortable? | Best overall Chelsea boot | Affordable Chelsea boots | Stylist-approved Chelsea boots | Editor-approved Chelsea boots | FAQs | How we chose | Meet our experts

How do I style Chelsea boots?

Chelsea boots are incredibly versatile and can be styled in so many different ways. 

If you want a more casual look, Appelt suggests pairing Chelsea boots with skinny jeans or straight-leg jeans with a basic tee or a casual button-down shirt. She even says layering this outfit with a lightweight jacket will take it from casual to chic. 

If you prefer a more bohemian look, style a pair of brown suede Chelsea boots with a flowy maxi dress or skirt.

As for fashion stylist and personal shopper Elisabeth Kassab, jeans and Chelsea boots are a match made in heaven. 

“Straight-leg jeans or baggy jeans and a crew neck sweater would be my go-to,” Kassab says. “But any type of straight-leg pants and sweater or long coat is what I would reach for.” 

Chelsea boots can transition into the office too. Appelt says pairing a black pair of Chelsea boots with tailored trousers and a crisp, tucked-in blouse will make you the best dressed in the office. Also, adding a blazer will be the cherry on top of a perfect fall outfit.

Do Chelsea boots go out of style?

The Chelsea boot proves it’s possible to be trendy and timeless at the same time. Los Angeles-based stylist Carrie Cramer says that Chelsea boots “have remained a constant, comfortable, sleek boot option for decades.”

When you think of a classic Chelsea boot, a sleek black boot with an elastic gore likely comes to mind. However, many new styles have put an elevated twist on this fall classic, incorporating different colors, textures and materials. 

“Chelsea boots are simultaneously utilitarian, streamlined and can be styled very edgy,” Appelt says.

If you’re a newbie when it comes to boots, don’t fret. Cramer shares the classic Chelsea boot will be the perfect addition to any outfit you’re planning to rock this fall. 

“Chelsea boots look very chic and modern with cropped jeans or black trousers no matter the season,” she adds.

But if you’re a fall footwear pro, a green-colored Chelsea boot may be a more “fashion-forward“ choice to zhuzh up your wardrobe.

Are Chelsea boots comfortable for walking?

Chelsea boots are also surprisingly comfortable and can be worn for any kind of occasion.

“Since most Chelsea boots are flat, they are a great option when you need to be on your feet all day or you are traveling,” Cramer says. “They are also a perfect choice for city living. For my life in Los Angeles, I wear a Chelsea boot to work and roll it into date night with my husband.”

Cospito also suggests that Chelsea boots with lug soles work well for the winter since they provide a bit more traction when it comes to braving the elements. When the warmer months roll around, opting for a sleek Chelsea boot in a lighter color such as brown or beige will make your look feel fresh.

Something to note

  • Chelsea boots can be a pricey wardrobe staple. Kassab says they are an investment piece because they are normally made with leather. Appelt suggests that buyers go for the best quality Chelsea boot that they can afford.

Best overall Chelsea boot

Steve Madden Thyra Chelsea Bootie

Material: Synthetic leather, suede | Heel height: 1.25 inches | Colorways: 2 | Sizes: 6-11, including half sizes

Complement your looks this fall with this classic Chelsea silhouette. These Thyra Chelsea booties from Steve Madden add simple style to every outfit. The lug soles and dual elastic panels make these a comfortable choice for any outfit. They also come in a brown suede perfect for the season.

One reviewer said, "This is my first boot purchase of the upcoming season and I absolutely love them. The suede is soft and feels quality. True to size and feels comfortable."

Budget-friendly Chelsea boots

A New Day Chelsea Rain Boots

Material: 100% PVC (Polyvinyl Chloride) | Heel height: 1 inch | Colorways: 2 | Sizes: 6-12

I (Domonique) has had these Chelsea rain boots for over three years and she says they still look brand new. The material has a matte finish that makes these boots stylish and easy to clean. Plus, they have a low-block heel and a pull-on tab at the back for easy wear.

One verified reviewer said, “These are the best rain boots you’ll ever find. Comfy and very sturdy. Proven during monsoon-type conditions and muddy terrain at an outdoor festival. Feet stayed clean and dry. Definitely worth it.”

Marc Fisher Rainy 2 Rain Boot

Material: Synthetic plastic | Heel height: 1 inch | Colorways: 1 | Sizes: 6-11

Don’t let rain stop your style. These Marc Fisher rain boots are designed to keep your feet dry and stylish on those wet and gloomy fall days. The double elastic gores make this shoe easy to slip on and reviews say these shoes run a bit narrow due to the almond toe.

Dolce Vita Coen H2O Boots

Material: 100% PVC (Polyvinyl Chloride) | Heel height: 1 inch | Colorways: 2 | Sizes: 6-12

Step out in style with these Dolce Vita heeled Chelsea boots. The chunky platform base adds a dramatic flare to any fall outfit. While many reviews say they run a bit small, one reviewer says, "I love this boot for styling with skirts and dresses because the of the taller shaft height! This is a great transitional boot, plus they are so comfortable!"

Steve Madden Laurely Chelsea Bootie

Material: Synthetic leather | Heel height: 2.38 inches | Colorways: 2 | Sizes: 6-11, including half sizes

The classic silhouette of this Chelsea bootie from Steve Madden makes it a wardrobe staple. They feature a stacked wooden heel, round toe and dual elastic panels to slip them on and off with ease. They also have a lightly padded footbed to give your fabulous fall outfit extra support.

Best Chelsea boots, according to stylists

Journee Collection Rorke Chelsea Boot

Material: Vegan leather | Heel height: 2 inches | Colorways: 4 | Sizes: 6-12, including half sizes

Cramer says she loves these boots from Journee Collection, especially since they come in a variety of fun color options. “This style looks great any day of the year but [it’s] also a perfect choice for those days when you don’t know what the weather will be like,” she adds. The Tru Comfort Foam insole in these Chelsea boots makes them the perfect pair for a day of long walking. 

Dolce Vita Stormy H2O Waterproof Chelsea Boot

Material: Waterproof synthetic plastic | Heel height: 1.3 inches | Colorways: 3 | Sizes: 6-10

Never sacrifice style for comfort with these chic H2O waterproof boots. The synthetic lining in these boots will keep your feet dry on a fall rainy day. Plus, the dual elastic gores make it easier to slip on this statement shoe.

Best Chelsea boots, according to editors

Sam Edelman Women’s Laguna Chelsea Boot

Material: Leather, suede | Heel height: 1.5 inches | Colorways: 17 | Sizes: 5-11, including half sizes

Senior partnerships editor Francesca Cocchi wore these weatherproof boots all fall last year. “They’re perfect for those rainy days when you still want to rock a cute outfit. I have the desert olive color but there are a bunch of stylish color combos available to suit your style,” she says.

This style comes in suede and leather with 17 different colors to choose from. However, reviews say they run a bit narrow around the toe.

Wolverine Women's Torrent Waterproof Chelsea Boot

Material: Waterproof full-grain leather | Heel height: N/A | Colorways: 3 | Sizes: 5-11, including half sizes

Production associate Audrey Ekman recently bought these Wolverine waterproof boots that will transition perfectly into the winter months.

"I’m from Minnesota where there’s usually snow on the ground from December to March and when I go home for the holidays this year I’ll definitely pack these!" she says.

These Chelsea boots also have a fleece lining with Wolverine DuraWarm insulation plus moisture control. The rubber lug sole on these boots provides traction and grip for any fall surfaces you face.

Dr. Martens Leonore Chelsea Boot

Material: Leather | Heel height: 1.12 inches | Colorways: 1 | Sizes: 5-11

Dr. Martens are a fall fashion staple and these brown Chelsea boots do not disappoint. These are Goodyear-welted for long-lasting durability, with the upper leather and sole sewn together in a z-welt stitch. 

Editorial assistant Sierra Hoeger said the ankle tab on these boots makes it easy to slip them on and off with leggings, jeans and tights. “They have a sherpa lining — which I theorize is why I didn’t get the classic blisters everyone complains about with Docs,” she shares. Reviewers say these boots run true-to-size and are surprisingly lightweight. 

Cologne Arlo 2 Tan Leather

Material: Leather, suede | Heel height: 0.78 inches | Colorways: 4 | Sizes: 6-12, including half sizes

SEO writer Jannely Espinal says this style is similar to the beloved, and sold-out, Orinoco2 Chelsea Boots. “What I love about these boots is the stretchy panels on the sides of the ankle for easy on and off."

“These are my go-to for the fall season and they also have one of the most comfortable footbeds for walking and commuting," she adds. The boots have a sturdy outer sole keeping your feet safe and dry as the winter winds come in. 

Frequently asked questions about Chelsea boots

How we chose the best Chelsea boots

In order to find the best Chelsea boots on the market, Shop TODAY gained expertise from multiple experts. We dug deep into dozens of customer reviews and made sure that we picked a mix of both high-end and budget-friendly Chelsea boots that work with everyone’s style.

Meet our experts

  • Gloria Cospito is a New York City-based personal stylist. Cospito has styled for film, television, digital, print and more. 
  • Carrie Cramer is a wardrobe stylist, personal stylist and costume designer based in Los Angeles. Cramer has been in the styling industry for over 20 years dressing all body types and shapes. 
  • Dr. Miguel Cunha is a foot and ankle surgeon based in New York City. Dr. Cunha has experience in a wide array of foot and ankle conditions, including reconstructive surgery.
  • Elisabeth Kassab is a fashion stylist and personal shopper who specializes in street style looks, brand campaigns and capsule wardrobes. She’s the founder of STYLISTCHECK, a platform where she curates outfits for her followers to shop. 
  • Kim Appelt is a celebrity fashion stylist and author of Style for EveryBODY. Appelt’s mission is to help people love themselves and find a style that speaks to their personal truth.