The 23 Best Chelsea Boots for Men, From Backyard to Black Tie
Name a more versatile boot than the classic Chelsea. We'll wait.
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Everyone knows the Chelsea boot. From James Dean and The Beatles to Timothee Chalamet and Virgil Abloh, the style has been synonymous with well-dressed figures for decades, a staple of fall/winter footwear for office bros and creative directors alike that goes with everything from cozy jeans to fisherman sweaters to tuxedos — suited and booted, as we like to say — without ever getting stale. They’re timeless, ultra-versatile and, in the case of the best, straight style dynamite.
- The Best All-Around Chelsea: Blundstone #500 Boot
- The Best High-End Chelsea: R.M. Williams Comfort Craftsman Boots
- The Best Office Chelsea Boot: Astorflex Bitflex Boot
- The Best Outdoor Chelsea Boot: Keen Revel IV Winter Boot
- The Best Weatherproof Chelsea Boot: Hunter Refined Slim-Fit Boots
- The Best Classic Menswear Boot: Saint Laurent Wyatt 30 Suede Boots
- The Best New Menswear Boot: A Kind of Guise Parioli Boot
- The Best Slipper Boot: Greys Sherpa Slipper Boot
What Is a Chelsea Boot?
The Chelsea boot, also known as a paddock boot, traces its origins back to the 1800s, although it didn’t rise to prominence until later, and is commonly denoted by elastic paneling — affording an easier, pull-on fit — pointed toe and high silhouette. Originally designed for equestrian and other physical pursuits, the shoe has evolved to span the entire frequency of functionality, from sleek leather styles best worn with a suit to rugged, lug-soled joints (maybe you’ve heard of the Blundstone) that’ll serve as well in the backcountry as they will in the backyard.
What Makes a Good Chelsea Boot?
According to heritage bootmakers Crocket and Jones, to be regarded as “high quality,” the classic Chelsea must be blocked, or built with shaped leather vamp castors cut from a pressurized blade. We find this way of thinking to be outdated — there are tons of new methods and labels making excellent boots outside the original construction. However, it’s worth noting that a Chelsea is denoted by its ankle-height shaft and leather or suede upper, and we’re inclined to agree with that baseline.
The biggest indicator of the quality of a Chelsea (or any boot, for that matter) is the upper material: whether a supple suede or treated pebble leather — for winterized styles, even synthetic, weatherproof blends are used — a quality upper cut from trusted sources (Italian leather and suede often prove the best) is always the way to go. Other standard hallmarks of craftsmanship — Goodyear welting, durable rubber soles — also play a factor in the grade of your boot.
Even with that knowledge, it can be hard to pluck the wheat from the chaff when it comes to the old paddock boot, considering the popularity of the style and the thousands of versions that exist. To help you decide which pair is right for you, we’ve compiled a list of the 18 best Chelseas — ones that we’ve put serious mileage into, ones that carry the weight of legacy, and some aspirational picks for you bazillionaire readers — for you to explore. Below, the 23 best Chelsea boots for men in 2023 and beyond.
The Best Chelsea Boots for Men in 2023:
The All ‘Rounder:
Blundstone #500 Chelsea Boot
Despite his silly mustache and proclivity to complicated coffee brewing, your buddy (also, your boss, sister, and anyone else who raves about their pairs) is right: Blundstones are objectively amazing. No other entrant on this list can do as much as well as the Tasmanian-born boot: the #500, Blundstone’s hard-working and versatile iteration, is just dressy enough to pass inspection but features all the bells and whistles, from a weatherproof 2.5 mm oiled leather upper to a Polyurethane midsole, to keep your tootsies protect, warm and most importantly, stylish as hell.
The Expensive, But Worth It:
R.M. Williams Craftsman Chelsea Boots
While we’re conscious of tightening budgets and increasing prices, we strongly recommend that, if you can swing it, Aussie-made R.M. William’s Craftsman Boots are the way to go. Straddling the dressy-workwear line to perfection, they are one of the few styles that can handle a suit and a shovel with similar aplomb. The secret lies in the one-piece leather upper and Goodyear welted-construction: if you treat them right, these bad boys should last you for years to come.
The Office Boot:
Astorflex Bitflex Chelsea Boot
Looking for something more at home at the office than the outdoors? The handmade Astorflex’s Bitflex more than looks the part in a business-casual uniform and maintains the added benefits of sporting a 100% natural crepe rubber sole, one of the softest footbeds we’ve tested. While the Italian-made boots might not be our first choice for braving it in the wilderness, they’re certainly our go-to for a long day pretending to work in your corner cubicle.
The ATC (All Terrian Chelsea):
Keen Revel IV Winter Boot
Keen’s Revel IV might have the paneling and pull tabs commonly associated with the style, but the winterized style has more in common with a bulldozer than a standard Chelsea. Nonetheless, the sheer mass of waterproof leather and grippy rubber, coupled with a lock-down fit and a recycled PET insulation rating of -25 degrees, make them the only slip-ons we’ll be reaching for as snow piles up and temps drop below freezing.
The Weatherproof Workday Pick:
Hunter Refined Slim-Fit Chelsea Boots
You might not know that Hunter’s Refined Chelsea Boots are entirely waterproof at first glance, and that’s kind of the whole point. Designed specifically for a sleek, sophisticated look when conditions get sloppy, the boots maintain that signature touch of Chelsea class, without losing the handcrafted, waterproof finish Hunter rain boots are so known for.
The Classic Menswear Choice:
Saint Laurent Wyatt 30 Suede Chelsea Boots
Anyone familiar with the wild west of menswear blogs, forums and subreddits will surely remember the chokehold that Yes Saint Laurent’s newly rebranded Saint Laurent and its iconic Hedi Slimane-designed Wyatt Chelsea had on the style-obsessed hive mind. As it turns out, it wasn’t just an arbitrary fixation: as they say, the devil’s in the details, and the Wyatt’s plethora of calculated nuances — tan Italian suede, snappy elastic paneling and that model-thin shape YSL is so known for — makes it one of the finest pairs you can purchase today.
The New Menswear Choice:
A Kind of Guise Parioli Boot
A Kind of Guise might not be a household label (yet), but the German ready-to-wear brand’s commitment to small-batch craftsmanship has not gone unnoticed. Case in point: the new Parioli Boot, part of AKOG’s F/W launch, is finished with Italian-sourced leather, tanned to a handsome “cognac” to complete it’s double-stitched, Vibram-soled body.
The Chelsea Slipper:
Greys Sherpa Slipper Boot
Are Greys’ Sherpa Slipper Boots actually Chelsea Boots? When you factor in the sherpa fleece lining, reinforced toe box and handmade Portuguese construction, does it really matter?
More Chelsea Boots We Love:
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