9 Stylish and Comfortable Chelsea Boots That Will Compliment Any ‘Fit

This year, summer carried on far too long, and fall barely grazed us. But, as we enjoy the last of the crisp autumn season and brace ourselves for the cold, we only need to answer one important question: What boots are we wearing? As a strong advocate for timeless and classic pieces, only one boot comes to mind, the Chelsea. Therefore, I’ve found nine amazing styles you just have to try this season that will carry you for many more to come. Scroll down for a few of the best Chelsea boots that are stylish, comfortable, and versatile enough to fit effortlessly into your existing wardrobe.

The best Chelsea boots, at a glance:

Best bold take:Madewell Ingrid Chelsea Boot, $198Most modern:Zara Treaded Chelsea Boot, $70Best value:No Boundaries Knit Chelsea Boot, $30Most deceivingly comfortable: Naturalizer Lug Sole Chelsea-Inspired Bootie, $120Most stylish:Mango Leather Pointed Ankle Boots, $140Best for travel: Samuel Hubbard Van Ness Chelsea Boot, $185Best waterproof:Sperry Torrent Rain Boot, $80Best on-trend:Sam Edelman Bronson Boot, $170Best outdoorsy:Barbour Nimbus Chelsea Wellies, $120

The Chelsea boot is so classic that it originated as a riding boot in the mid-1800s for Queen Victoria and gained its popularity around the 50s and 60s in London’s Chelsea neighborhood. Today, standing the test of time, it’s transformed into many different variations that it is almost impossible to pick just one. In fact, Fashion Police alum Melissa Rivers suggests having two pairs.

“Chelsea boots are a classic fall staple. They are simple, effortlessly stylish, and can go easily with just about anything. They’re so versatile that having two pairs, one more casual and one dressier, wouldn’t hurt!” says the actress. Ready to get shopping? Check out nine of the best Chelsea boots, below.

Shop 9 of the best Chelsea boots

Madewell Ingrid Chelsea Boot — $198.00

Sizes: 5—11 (half sizes available) | Colors: 2 | Materials: Full grain leather

Add a bit of flair to your wardrobe with this bold take of this classic boot. A little bit vintage and a little bit western, this 100% leather boot (sourced from a tannery certified by the Leather Working Group) is sure to make heads turn. Made with a 31% recycled sole, this is just another brand that is going in the right direction.

Pros: 

• Sleek silhouette
• Sole contains recycled materials
  
• Leather sourced from a LWG-certified tannery

Cons: 

• Pointed toe might not work for all foot types
• Only two color options

Zara Treaded Chelsea Boot — $70.00

Sizes: 5—11 (some half sizes available)| Colors: 1 | Materials: Faux leather (polyurethane), elastic

A chunky soled rendition of a classic, this style isperfect for channeling that classic Caroline Bessette-Kennedy vibe with its modern sleekness and it girl factor. The side elastic goring and back pull tab makes putting on and taking off, the perfect style for the gal on the go. 

Pros: 

• Cool, chunky aesthetic
• Completely vegan
• Elastic panels for easy entry

Cons: 

• Limited sizes and colors
• Taller boot shaft might not work for all calves

Best value: No Boundaries Knit Chelsea Boot — $30.00

Sizes: 6—12 | Colors: 3 | Materials: Polyester upper, rubber sole

Further proof that style doesn’t have to be expensive. At just $30, this version is reminiscent of a popular designer style that is popular with celebrities and top fashion editors. With a chunky sole and knit upper, it’s giving IT girl vibes for every woman. 

Pros: 

• Zipper for easy entry
• Budget-friendly price
• Three versatile colors

Cons: 

• No half sizes

Most deceivingly comfortable: Naturalizer Lug Sole Chelsea Inspired Bootie — $123.00

Sizes: 6—12 (half and wide sizes available) | Colors: 2 | Materials: Faux leather

Don’t let the three-inch heel fool you, Naturalizer is well known for comfort. Made with the brand’s Contour+ Comfort technology, these beauties promise all day wear with all day comfort. Style with a slim denim, button up and trench for the classic about town vibe. 

Pros: 

• Extensive size range
• Designed with comfort in mind
• Zipper for easy entry

Cons: 

• Heel may be too tall for some

Most stylish: Mango Leather Pointed Toe Boots — $140.00

Sizes: 5—10 (half sizes available) | Colors: 1 | Materials: Real leather upper

Made of 100% bovine leather, this cowboy style version is a fun take on the Chelsea boot . The pointed toe adds a sleek finish to this timeless design. Perfectly paired with a slim black pant, a chunky knit sweater, and dark sunnies for a cool girl aesthetic. 

Pros: 

• Real, bovine leather for added durability
• Sleek pointed silhouette

Cons: 

• Only one color available
• 3-inch heel may be too tall for some

Best for travel: Samuel Hubbard Van Ness Chelsea Boot — $185.00

Size: 5—11 (half sizes available) | Colors: 3 | Materials: Leather and nubuck upper, lightweight synthetic sole

An almond-shaped toe adds to the modern sleekness of this traditional style of boot. Handcrafted by artisans in Portugal, every detail was carefully thought through. It’s lightweight style and comfort makes this style the perfect choice for travelers whether exploring a new city or walking the countryside. 

Pros: 

• Removable insoles with arch support
• Real leather upper
• Lightweight support for travel

Cons: 

• Pricier option

Best waterproof: Sperry Torrent Rain Boot — $80.00

Sizes: 5—12 (some half sizes available) | Colors: 14 | Materials: Waterproof rubber upper

The durable rubber design of this Sperry boot makes it perfect for rainy and slushy days alike. The interior has micro-fleece for added warmth, and the lugged outsole has non-stick traction to keep you on your feet, even when it’s slippery outside. Plus, it comes in more than 10 colors so you can find the perfect shade to fit your style. 

Pros: 

• Waterproof
• Tons of color options
• Grippy outsole for less slips

Cons: 

• Causal design is tougher to dress up

Best on-trend: Sam Edelman Bronson Boot — $170.00

Sizes: 5—11 (half sizes available) | Colors: 6 | Materials: Suede or faux leather

Made with a suede leather upper, this style is great for elevating a casual everyday look for that modern, laid back feel. The square toe and block heel adds to the modern sophisticated vibe, plus it’s available in a range of neutral brown, black, and taupe hues. 

Pros: 

• Soft suede makes it easy to dress up or down
• Range of neutral colors available
• Comfortable low heel

Cons: 

• May be tough to get on and off

Best outdoorsy: Barbous Nimbus Chelsea Wellies — $120.00

Sizes: 5—11 (whole sizes only) | Colors: 2 | Materials: Rubber, synthetic textile lining

Rain or shine, these boots are the perfect addition to your wardrobe. From the brand synonymous with the British countryside, Barbour, these waterproof rain wellies are seriously stylish and the best way to elevate your style on the gloomiest of days. 

Pros: 

• Rugged and durable
• Waterproof design
• Elastic panels for easy on and off

Cons: 

• No half sizes
• Only two colors