When you think of your wardrobe essentials, you probably think of a great pair of slippers. And if they don’t, they should! Ankle boots or Chelsea boots are some of the most versatile fashion items you can invest in; they go with almost any look, slip on and off easily, and wear well over time.

A bit of history, the first boots with elastic inserts date back to 1837, when different styles were trendy thanks to technical innovations such as sewing machines and vulcanized rubber. Like today’s Chelsea boots, these early versions were flat and had an ankle-length shank made of leather with a flexible wedge on the sides for easy on and off, fashion expert Maureen Lento Brewster tells Birdie. The style returned to popularity in the 1950s, “but included a higher Cuban heel and a tapered toe to complement the slim pants that became popular during this period.” They were called Chelsea boots because of their association with the British quarter that was at the center of Swinging London in the 1960s.

Since then, the relationship between fashion and nostalgia has seen Chelsea boots come and go, varying in heel height, shape and manufacture. “Originally they were only made in leather with a very limited color palette, but now they are available in many different colors, materials and patterns according to trends,” says Lehto Brewster. And given their versatility, stylish people make sure they always have a quality pair on hand.

With all of this in mind, we used our internet research skills and expertise in brands, shoe materials and shoe construction to round up the best Chelsea boots on the market across a range of categories. For example, KHAITE’s high soles and contrast stitching are one of the most eye-catching options, while Isabel Mirant’s monochrome black pair offers a glossy edge. Similarly, Italian Everland leather is very classic and goes with almost any outfit. Birkenstock, Dr. Martens and Hunter all offer sturdy pairs that are perfect for a variety of weather conditions.

Best of all: Isabel Marantz Caste leather Chelsea boots

Isabel Mirant’s leather Chelsea boots are so classic that they go perfectly with everything from denim and tailored trousers to dresses and skirts of various lengths. Although they seem silly compared to the other songs on this list, we can’t help but notice their value for their quality and versatility. Constructed from black leather, they stand on chunky rubber soles with a manageable 1-inch heel. They also have elastic sides at the edges, so you can easily put them on and take them off.

Best Value: Dr. Martens Flora Chelsea Boot

Dr. Martens Flora Chelsea Boot is by far the best value for money Chelsea boots. They are made of smooth, shiny leather with a low, matte base without visible construction threads. They’re also non-slip, so they’re perfect for use in the rain or snow if you want to keep that super shiny look.

Best Budget: Everland Italian Leather Chelsea Boot

Everland’s Chelsea boots exude elegance, timelessness and great value (under $200). The upper is made from Italian leather and features a round toe and leather tongue. For optimal comfort, it has flexible panels on both sides, and for stability, the soles are made of textured rubber. These are the everyday leather boots that you can wear from fall to spring and pair perfectly with everything from black or flared knit jeans to a floral midi dress.

Best for Outdoors: Bloodstone Thermal Chelsea Boot

Considered one of the most durable footwear brands, Bloodstone has introduced its Thermal series. Here’s our best advice for keeping your feet warm, dry and stylish. With removable cutout insoles, waterproof leather and stitching, and an “ergonomically shaped flexible toe cap,” these Chelsea boots have all the benefits of a bulky, purely functional winter boot, but also add a touch of street style. Don’t be afraid to hit the trails or step into a puddle with this pair.

The best patent: Todid’s leather ankle boots

For maximum shine and some lift, Tod’s is just what you are looking for. Made in Italy in glossy patent leather, the Chelsea boots rest on rubber soles with a wide heel. Wear them with straight jeans, a knitted midi skirt or, as NET-A-PORTER suggests, a delicate tea dress.

Best Vegan: Stella McCartney Trace Chelsea Boot

British designer Stella McCartney is known for her dedication to veganism in fashion, so it’s only natural that we call her Chelsea boots the best in this category. Made in Italy from faux leather, this pair features elasticated corners, jacquard fabric tabs with the label logo and thick rubber soles.

The best pointy shoes: Acne Studios Chelsea boots

Acne Studios designer Johnny Johansson is diving on the edge of his luxury shoes made in Italy. These leather ankle boots embrace the classic Chelsea style of smooth black leather, with a subtle gunmetal finish that hugs the toe. They are low-cut and have corners and a tab on the back for easy wearing and taking off.

Best jersey: Chloe Jamie Chelsea Boot

Feel at home in Chloe’s innovative Chelsea boots. We like that the designer uses the jersey to warm the boot and replace the typical elastic corners. The base of the ear and the block heel are equally practical and elegant, and overall the style balances the masculine and feminine design features.

The best weather resistance: the Aquatalia Leila waterproof leather shoe

Few luxury brands prioritize waterproofing like Aquatalia. The brand prides itself on its ability to combine distinctive Italian fashion and design with quality and comfort. The Leila style of the brand is a great demonstration of these goals and values. It keeps feet dry in wet conditions and adds shine and versatility in any weather, something people living in true four-season climates should really appreciate.

The best eco-friendly: Gianni recycled rubber Chelsea rain boot

Chunky brim boots are all the rage right now and Gianni creates a pair that are hard to resist in terms of style and durability. Made in Portugal with 50% recycled rubber, it has a matte finish and features branded tabs and stretch panels. We love them because they fit just about anything, add just the right amount of sturdiness to delicate dresses, skirts and other tailored looks, and complement combinations of raw denim and T-shirts. For extra warmth, choose the version with an artificial cutter.

Best Use: Birkenstock Stalin Chelsea Boot

Birkenstock is known for comfort and support, and the Stalin boot is no exception, reviewers say. Made in Portugal, this Chelsea model features a molded cork sicklier for arch support and an outsole designed for superior traction. If you are going to wear socks, users say you should go one size up than your normal size.

Best length: KHAITE Calgary leather Chelsea boots

KHAITE’s Calgary Leather Chelsea Boots prove that a little height is all you need when it comes to boots. The taller shaft is a twist on the classic Chelsea boot style and gives the illusion of leg length. In addition, the thick sole with white stitching is modern and easy to combine with many outfits.

What to look for in Chelsea boots

To build

Most Chelsea boots are made from leather, suede or rubber and each has its own charm. The leather is classic, comfortable and long lasting, while the suede is much easier to put on and difficult to keep in great condition. (So ​​if you’re worried about your shoes breaking after some wear, dark leather might be the best choice for you, especially one that’s made to be weatherproof. Otherwise, suede and lighter leathers are great. clothing.) Rubber is very durable, but not the most environmentally friendly unless made from recycled materials.

Module

Chelsea boots are skinny ankle boots that usually have a round toe, a low profile sole and a very low heel. However, many classic Chelsea boots have pointed and square toes, as well as thicker soles, higher heels, and higher shaft heights.