11 designer-approved Chelsea boots for every wardrobe

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Trends come and go in fashion, but there are wardrobe basics that will always stand the test of time. You know – the white sneakers, the black leggings, the perfect jeans – the list goes on. However, there is another essential element that we must add to this list of fashions that never go out of style: the Chelsea boot.

Yes, Chelsea boots have been around for a while and aren’t necessarily new, but in recent months the designers have given them updated versions that make them feel fresh and on-trend.

“Chelsea boots are a staple of any shoe,” New York-based personal stylist Gloria Cospito told us. “This season, the Chelsea boots get a streetwear upgrade with taller uppers and chunky soles.”

We’ve seen the spiked sole trend play a lot this season on almost every type of shoe, so we love that the upgraded Chelsea boot is a stylish option that you can wear almost anywhere.

Are Chelsea boots going out of style?

Los Angeles-based celebrity, wardrobe and personal stylist Carrie Cramer says Chelsea boots “have been a consistent, comfortable and stylish boot option for decades,” making them a timeless staple. Going forward, however, Cramer believes we’ll see “a return to the classic Chelsea boot with a lower heel in several years. For now, enjoy the extra height and rugged-chic style.”

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

If you don’t already own a pair of Chelsea boots, Cramer recommends that you go for a classic black style first. However, a cool green color may be a more “edgy” choice for the more seasoned Chelsea boot wearer, as it “can go with anything in your wardrobe.”

“Chelsea boots look very chic and modern with cropped jeans or black pants, whatever the season,” Cramer said. “This winter, I can’t wait to wear Chelsea boots with joggers and a chunky sweater or cropped jacket.”

Are Chelsea boots comfortable for walking?

In addition to their fashionable look, Chelsea boots are also surprisingly comfortable and can be worn for any type of occasion.

“Since most Chelsea boots are flat, they are a great option when you need to be on your feet all day or when you are traveling,” Cramer said. “They’re also a perfect choice for city living. For my life in Los Angeles, I wear a Chelsea boot to work and put them on to hang out with my husband.”

Cospito also says that the Chelsea boots with notched soles work well for the winter, as they offer a little more traction when it comes to braving the elements. And when the warmer months come back, opting for a stylish Chelsea boot in a lighter color like brown or beige will make your look feel cool.

Best Chelsea Boots, According to Stylists

We asked Cramer and Cospito for the best Chelsea boots they own or have their eyes on – and their choices didn’t disappoint. Read on for the boots that were made to walk this fall.

Rorke Chelsea Boots Journee Collection

Cramer says she loves these boots from the 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 Boots

The boot Cramer has in his closet? This chunky pair of Madden Girl. “I love that they are a little punk rock combined with a sleek style,” she said.

A New Day Ellie Chelsea Boot

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

Dolce Vita Stormy H2O Waterproof Chelsea Boots

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

Waterproof Boot Sam Edelman Laguna

Cospito chose this white boot with a notched sole as a stylish shoe option for this season. Not only are they trendy, but they will also keep your feet comfortable and dry, thanks to a “synthetic” insole and waterproof leather material.

Coach Lyden Leather Chelsea Boot

You can’t go wrong with a leather Chelsea boot. This platform style from Coach is another of Cospito’s picks that features a rounded toe and pull buckles for easy wearing.

ASOS Design Wide Fit Chelsea Boots

Need a wider style? These boots feature a loose fit and a slim toe silhouette. Reviewers love the faux leather construction and comfortable fit.

Aerosoles Boots Emelia

Cramer loves that these boots add height and a lot of edge to any look. In addition, the platform sole is made with “advanced technology” which gives them a super comfortable feel.

Calvin Klein Demmie Chelsea Boot

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 the most is that they’re on sale right now for just $ 75.

Madewell Perry Chelsea Boots

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

Madden Girl Cindy Chelsea Boots

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

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