Striding with confidence into early fall is paramount: Arguably the best season for menswear, fall brings with it an embrace of rich, hearty fabrics, blazing colors and old favorites made new again, like the Chelsea boot. With historic roots dating back centuries, the Chelsea boot remains a style icon both classic and modern, prized for its easy wearability with everything from tailored trousers to classic blue jeans. Options both luxurious and slightly more rugged abound, as brands turn to the Chelsea’s pull-on design for a mix of both tailored and workwear inspiration. Opt for a pair with a sturdy wedge outsole for weekend tailgating, or slide into an ultra-sleek European set made to be styled with a finely tailored fall suit. Check out some of the best Chelsea boots available to shop now.
Astorflex Bitflex Chelsea Boots

The good folks at Austin-based Americana retailer Huckberry have a knack for unearthing some of the coolest under-the-radar-brands on the planet. And that certainly goes for Italy’s family-owned Astorflex: For about a decade now, the brand has been sustainably crafting absurdly comfortable, fairly priced Chelsea boots, like this pair set atop a sturdy yet soft gum rubber outsole. $250
Thursday Boots Hickory Chelsea Boots

For more than a decade now, Thursday Boots has been making it easy for guys looking to upgrade their boot game, offering seamless online ordering and surprising quality given the agreeable pricing. If you’re in the market for a starter set of Chelsea boots, look no further. $199
Rhodes Footwear Boone Wedge Chelsea Boots

The Chelsea boot can be a surprisingly hard-working shoe, if you find one crafted from the right materials (like bovine leather) that happens to be set atop a sturdy wedge outsole. These beastly boots are as fit for a rock concert as they are for a day in the field, and they’re on sale right now at Huckberry. $162 (was $250)
Carmina Shoes Simpson Chelsea Boots

There’s passion and luxury in every step of the footwear craftsmanship that goes into Carmina Shoes. With a family-owned lineage and an intense commitment to quality, its handsome and refined boots and shoes proudly showcase the brand’s heritage on the island of Mallorca. The Simpson Boots in particular are remarkable in terms of leather quality, a sleek yet comfortable fit, and investment-worthy construction. $685
Todd Snyder Nomad Chelsea Boots

For years, customers clamored for award-winning designer Todd Snyder to produce footwear: While the company had collaborated with the likes of P.F. Flyers and Tricker’s, the Nomad is the first launch bearing Todd Snyder’s namesake. The results are effortlessly cool, crafted from rich suede with a “TS” branded back pull tab and a streamlined silhouette. $398
Blundstone Classic #587 Chelsea Boots

Look closely, from Bushwick to London, and you’ll spot plenty of pairs of sturdy yet ridiculously comfortable Blundstone boots. The Australian bootmaker is having a moment, thanks to its expert blend of rugged form and casually stylish function. With water-resistant leather and a shock-absorbing outsole, consider these both festival and field-ready boots. $209
Dr. Martens Vintage 2976 Quilon Chelsea Boots

The Chelsea boot takes on a dash of punk-inspired, rock n’roll edge when done by Dr. Martens. The company’s signature yellow stitching air-cushioned outsole are part of the makeup, while two-tone textured leather should develop its own eye-catching patina over time. Find them now via the substantial Chelsea boot offering at Huckberry. $260
Tecovas Rugged Chelsea Boots

Pull-on boot styles have been prized for ranchers and cowboys dating back generations: The easy-on, easy-off style performs particularly well on horseback. And for pursuits both rugged and more leisurely, Tecovas (the wildly popular Western boot brand) delivers, with a dual-density outsole and tough-as-nails water and slip-resistant construction. Looking for Chelsea boots that can take a beating? You’ve found ’em. $225
LUCA Terra Slip On Chelsea Sneaker Boots

The Chelsea boot can take on many forms these days, including that of a sneaker boot: This pair boasts a thick, springy gum rubber outsole and supple leather upper construction. Hailing from Huckberry’s lineup of LUCA sneakers, these are as wearable with olive chinos as they are with wool trousers. $215
R.M. Williams Craftsman Chelsea Boots

Originally fashioned for workers and field hands in the wilderness of Australia (not unlike Blundstone boots), R.M. Williams’ boots today epitomize luxury and craft. With as distinctive a toe shape and build as any Chelsea boots on the market, consider these a stylish splurge you can wear with looks both Western-inspired (like blue jeans and a denim shirt) or tailored (as with a herringbone suit this fall and winter). $590