For classic style, Chelsea boots are a shoo-in every boot season. A solid pair is easily attainable on a budget, and the best Chelsea boots under $100 are stylish yet comfortable. The Chelsea boot was designed to be easy to slip on and off — a couple of easily recognizable features make this so.
Elastic goring on each side of the boot, along the shaft, makes it more flexible and is a sure sign of a Chelsea boot. These chic ankle boots generally have a pull tab at the heel for added ease when slipping into them. A round toe is another telltale characteristic, but pointy toe versions are around as well.
Typically, Chelsea boots are made of leather, though when you're looking for a pair under $100, most options will be faux leather. Leather is durable and flexible, but PU or artificial leather are easier to find in this price range, and have the benefit of being more lightweight. Some Chelsea boots are water-resistant or waterproof to double as rain boots — a natural transition with the Chelsea's characteristic rubber sole for traction, which helps prevent slippage in rainy weather.
The most common colors for Chelsea boots are black or brown — cementing them as a versatile closet staple — with either matte or glossy finishes. It's worth noting that even flat Chelsea boots have a bit of a heel, though it's usually under an inch and balanced by a platform at the shoe's front to remain walkable. However, there are high-heel versions of the boot.
With all this in mind, it's time to shop for the best Chelsea boots under $100, plus an extra splurge worth considering for rougher weather.
1. The Best Overall: An Under $100 Option Made With Real Leather
Made with a 100% leather upper-body, this designer Chelsea boot is a sustainable leather shoe by Clarks, a founding member of the Leather Working Group, which aims to promote sustainable business practices within the leather industry. This classic boot has a rubber sole that provides traction with a low heel that's less than an inch high. While there's no pull tab on these modern booties, the elastic goring makes them easy to slip on and the Cushion Soft Technology ensures long-lasting comfort. This pick comes in tan, black, and a nude pink leather — all of which keep their black goring.
Fans say: “I love these boots!!!!! Quality leather and extreme comfort. I have a wider foot so I always have to order a 1/2 size larger but because these boots have such soft buttery leather I wore them for about 5 hours to mold my foot into them and they have been perfect ever since! Would love another pair in camel brown leather!”
- Available sizes: 6–10
2. The Best Leather Chelsea Boot on a Budget
For the look of leather under $50, the Odema Chelsea boot is made from PU leather, but still delivers a comfortable fit with all the hallmarks of a Chelsea boot — particularly its low, 1.25-inch heel. The rubber sole provides the traction that people expect with this type of shoe. Reviewers report that this budget buy is comfortable enough to wear to work, however, you should expect a brief breaking-in period. This pick comes in black and brown with your choice of black or a mahogany brown with either leather or velvet lining.
Fans say: “Exactly what I was looking for. I seriously love these shoes. I normally wear a size 8 (and ordered an 8) and they fit great!...The material feels great and the soles are very sturdy. These shoes are super cute and I’m excited to wear...”
- Available sizes: 5.5–10.5
3. The Best Waterproof Chelsea Boots
With more than 1,300 reviews on Amazon, this highly rated Chelsea boot is loved for being cute, functional, and waterproof, too. Asgard's Chelsea boot is lightweight and durable thanks to the high-quality PVC material. The rubber outer-sole keeps you from slipping on wet or muddy ground, while the roomy toe area and padded footbed provide plenty of comfort, and the inner elastic fabric is edge finished to reduce rubbing at the ankle. With a matte finish and 1-inch heel with a half-inch platform, this is a classically attractive Chelsea boot that comes in a 10 different colors like classic black, silver glitter, a sunny yellow, and navy blue. Some options even have goring or outsoles in different colors.
Fans say: “I wanted something versatile that I could wear with everything but waterproof just in case it rained. Overall these boots were a great choice! They went with everything and most importantly, were very comfortable. I walked all day in them for 4 days straight with no issues...Great boot if you're not wanting to commit to a full rain boot all day and are not going to a snowy climate!”
- Available sizes: 4.5–12
4. The Best Chunky Heel Chelsea Boots
If you're looking for a Chelsea boot with a chunky heel, this faux leather number has a 3-inch heel that's surprisingly wearable. This pair is highly rated with more than 700 reviews from Amazon shoppers who love their comfort and walkability. Designed with a cushioned insole, they have a zipper along the shaft as well as the classic pull tab at the heel — so they're also really easy to get on and off. These come in your choice of suede or leather styles, with multiple color combinations to choose from, including pewter, wine, and black.
Fans say: “Finally found shoes that fit and are comfortable and cute! I have been looking for chunky black boots for months! I have returned everything before these...They are super comfortable right out of the box, tried them on with a medium thick sock. I might get a second pair. Heel height with the platform is very comfortable, just right. You can't go wrong for the price.”
- Available sizes: 5.5–11
5. A Doc Martens Dupe
This edgy pair of waxed, vegan leather Chelsea boots is a total dupe for Doc Martens and even water-proof, too. The unisex boots stand out with yellow Z-welt stitching and a branded pull tab, but there are a lot of great features inside the shoe, too. The optional plush fur lining makes them warm enough for winter, and the soft, moisture-wicking lining with a memory-foam heel pad makes them cozy and comfortable. These boots come in black, burgundy, and a marbleized black and burgundy.
Fans say: “I worried they would be too narrow, as [Doc Martens] are. I have wide feet and high arches. But the price was too good to pass up...They slipped on perfectly. The toe box is wide and roomy!! The height is perfect!!...I am SO IMPRESSED!!!”
- Available sizes: 5.5–14
Also Great: The Best All-Weather Option to Invest In
Sorel is a brand committed to functionality and fashion, and their full-grain leather Chelsea boot with seam-sealed waterproof construction is the one to wear during heavy rain or even snow. The canvas lining ensures these boots are still breathable, though. Additionally, the molded EVA footbed provides comfort and support, while a molded rubber midsole and outsole bring stability and traction when wearing these in wet weather. This pick comes in either black or a rich whiskey color called "burro."
Fans say: “These are my favorite boots ever. Comfortable as soon I put them on and comfortable even used heavily for a few months. Waterproof when tested in snow and slush. When these inevitably break down from heavy use I will buy another pair. That’s how much I love them. I usually wear and 8 but got an 8.5 based on reviews and they fit [perfectly].”
- Available sizes: 5–11
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