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

Stylists prove that Chelsea boots are more than just a seasonal staple.
Jeremy Moeller / Contributor / Getty Images

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.

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

"Chelsea boots are a footwear staple," New York City-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 over the last year 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.

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. 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.

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 season.

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.

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.

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.

Sam Edelman Laguna Waterproof Boot

Cospito picked this 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.

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.

More bestselling Chelsea boots to shop

J.Crew Factory Chelsea Rain Boots

Indulge in a practical pair of Chelsea boots with this multitasking pair from J. Crew. Not only are they cute, but they're also a pair that can withstand the elements as well. "I own some tall name brand rain boots and while those work great, they’re hard for me to walk in," one reviewer said, adding, "these are much better."

Lucky Brand Eabile Bootie

A new take on the Chelsea boot, reviewers recommend sizing up at least a half size with this pair, so then you can wear these with thicker socks to prevent blisters. Available in two colors — a taupe, sandy brown, and a cognac with black accents — these boots are "comfortable and flexible," according to reviewers.

Sam Edelman Daelyn Lug Sole Short Boot

Designed with a light color and lug sole, this Sam Edelman boot is perfect for those looking to stay on trend this season. This edgy option features classic side panels and back pull tabs and will blend right into your current wardrobe.

Dr. Martens 2976 Women's Patent Leather Chelsea Boots

For classic boot lovers, Dr. Martens are quintessential, and these Chelsea boots are a super stylish option. The upper and sole of these boots are heat-sealed and sewn together to provide extra comfort and durability.

Blundstone Chelsea Boots

Searches for Blundstone Chelsea boots rose around fall time last year — and rightfully so. While the product description says they're "always in style," we believe they scream fall. Reviewers rave about how comfortable and versatile this boot is, meaning you can wear it with jeans, a dress, to the office or a night out.