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11 stylist-approved Chelsea boots for every wardrobe

Though they're having a moment, stylists prove that Chelsea boots are more than just a seasonal staple.
Split image of two stylish Women wearing different styles of the Chelsea boot
Jeremy Moeller / Contributor / Getty Images

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Trends come and go in fashion, but there are wardrobe staples that will always stand the test of time. You know — the white sneaker, black legging, the perfect jeans — the list goes on. Though, there's another essential item we have to add to that list of fashions that never go out of style: the Chelsea boot.

Yes, Chelsea boots have been around for quite some time and aren't necessarily anything new, but in recent months, designers have been giving them updated takes that make them feel fresh and trendy.

"Chelsea boots are a footwear staple," NYC-based personal stylist, Gloria Cospito, told us. "This season, Chelsea boots are getting a streetwear upgrade with higher shafts and chunky soles."

We've seen the lug sole trend come into play a lot this season on nearly every kind of shoe, so we're loving that the upgraded Chelsea boot is a classy option that you can sport nearly anywhere.

Do Chelsea boots go out of style?

Carrie Cramer, a celebrity, wardrobe and personal stylist based in Los Angeles, says that Chelsea boots "have remained a constant, comfortable, sleek boot option for decades," which makes them a timeless go-to. In the future, though, Cramer thinks that we will "see a return to the classic Chelsea boot with a lower heel in several years. For now, enjoy the extra height and the tough-chic styling."

The classic Chelsea boot likely comes to mind as a sleek black boot with an elastic gore, but some of the elevated styles now incorporate different colors, textures and materials. Cospito says that white Chelsea boots are a "trendy graphic statement" right now.

If you don't already own a pair of Chelsea boots, Cramer recommends opting for a classic black style first. However, a fresh green color can be a more "fashion-forward" choice for the more experienced Chelsea boot wearer, since it "can go with anything in your wardrobe."

"Chelsea boots look very chic and modern with a cropped jean or black trouser no matter what season," Cramer said. "This winter, I can’t wait to style Chelsea boots with joggers and a chunky sweater or cropped jacket."

Are Chelsea boots comfortable for walking?

Aside from their fashionable look, 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 said. "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 says 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. And when the warmer months roll around again, opting for a sleek Chelsea boot in a lighter color such as brown or beige will make your look feel fresh.

Best Chelsea boots, according to stylists

We asked Cramer and Cospito for the best Chelsea boots that they either own or have their eyes on — and their picks did not disappoint. Read on for the boots that were made for walking this fall.

Journee Collection Rorke Chelsea Boot

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 added.

Madden Girl Truffle Bootie

The boot that Cramer has in her own closet? This chunky pair from Madden Girl. "I love that they are a little punk rock combined with sleek styling," she said.

A New Day Ellie Chelsea Boot

These affordable Chelsea boots touch on all of the classic features of the boot, but the 2-inch block heel and memory foam footbed give them an elevated twist.

Dolce Vita Stormy H2O Waterproof Chelsea Boot

Stylish and waterproof, these boots will take you from fall to spring just like that. They come in a bunch of different colors and are made with a rubber lug sole. Cramer says they're a "perfect choice for those days when you don’t know what the weather will be like."

Sam Edelman Laguna Waterproof Boot

Cospito picked this white boot with a lug sole as a stylish footwear option for this season. Not only are they on-trend, but they'll also keep your feet comfortable and dry, thanks to a "man-made" insole and a waterproof leather material.

Coach Lyden Leather Chelsea Bootie

You can't go wrong with a leather Chelsea boot. This platform style from Coach is another one of Cospito's picks that features a rounded toe and pull-up loops for easy wear.

ASOS Design Wide Fit Chelsea Boots

Need a wider style? These boots boast a wide-fit design along with a slim-toe silhouette. Reviewers love the faux-leather make and the comfortable fit.

Aerosoles Emelia Bootie

Cramer likes that these boots give some height and a whole lot of edge to any look. Plus, the platform sole is made with "cutting-edge technology" that gives them a super comfortable feel.

Calvin Klein Demmie Chelsea Bootie

Cospito says these Chelsea boots show off the classic style. From the sleek leather exterior to the almond-toe, there's so much to love about these boots — but what we love most is that they're on sale right now for just $75.

Madewell Perry Chelsea Boot

A truly elevated take on the Chelsea style, these boots from Madewell are delivering some serious height. The brown color feels refreshing, while the stacked heel gives it a unique look.

Madden Girl Cindy Chelsea Boot

These boots combine a little bit of edge with a lot of style. The lug sole gives them a trendy look, while the classic black and white designs make them a versatile piece in any wardrobe.

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