13 Ultra-Comfy Chelsea Boots to Wear With Jeans This Season

It’s officially November and that means it’s finally boot season. There are a bunch of different boot styles to choose from, but one that never goes out of style is the Chelsea boot. In the haze of trendy shoes that come and go, these boots have been here through it all! Chelsea boots are timeless, classy-looking and go with just about anything, not to mention they’re one of the most comfortable winter shoes of all . . . only if you choose the right ones!

There’s a neverending stream of options when it comes to Chelsea boots, but if you want to choose from a pool of ultra-comfy crowd favorites, read on! We gathered the best of the best from retailers like Amazon, Nordstrom and Quince. These boots pair beautifully with any style of jeans in your wardrobe — wide-leg, flare, bootcut, straight-leg, whatever!

We included options for all budgets, so let’s jump in!

1. Sassy queen: Slightly heeled and ultra-chic, these Kenneth Cole ankle boots have a suede upper and elasticized panels, making them easy to take on and off — $109 on Amazon!

2. Sherpa-lined find: This is the combo you didn’t know you needed. A leather-looking boot with faux fur lining, a cushioned footbed and a generous 1.5-inch platform check all the boxes — $90 on Amazon!

3. Comfy pick: Look no further for a lug-sole shoe that goes with absolutely everything in your fall and winter wardrobes — was $70, now $40 on Amazon!

4. Cinnamon suede: You don’t have to grab these sleek tapered boots in cinnamon brown, but you’ll get boundless compliments if you do — $100 at Quince!

5. Low wedge: Hey there, fashionista! These wedge boots have a 2.17-inch wedge heel and detailed stitching that makes them look much more expensive than they are — was $40, now $37 on Amazon!

6. Sorel pick: We can’t get enough of the block heel design of these waterproof boots. Your feet will stay dry whether you’re going through rain, snow or slush — $190 at Nordstrom!

7. Dr. Martens: These unisex boots couldn’t be more versatile. They’re a number-one bestseller on Amazon for a reason — was $130, now $95 on Amazon!

8. Total classic: You can’t say ‘Chelsea boot’ — or ‘boot’, for that matter — without thinking of Hunter. There are five classic waterproof pairs to choose from — $140 at Nordstrom!

9. Crowd favorite: Reviewers can’t get enough of this chunky Ugg pick. A waterproof leather upper paired with a foam footbed, lightweight rubber outsole and three-inch heel height is dreamy — $170 on Amazon!

10. Everyday staple: Look no further for a boot that you’ll want to wear every single day this fall and winter. Pair it with wide-leg jeans and an oversized sweater for an ultra-trendy look — was $140, now $55 at Nordstrom!

11. Sam Edelman: Dress it up or down for any occasion on your cold-weather agenda. This utilitarian-style Chelsea boot is waterproof, too — $150 on Amazon!

12. Classy act: A pointed toe and stacked block heel give this Clarks boot a one-of-a-kind flair — $150 at Nordstrom!

13. Our favorite hybrid: Somewhere between a Chelsea boot and a bootie, this go-with-everything find is guaranteed to elevate any fall ensemble — was $69, now $49!