The 23 Best Chelsea Boots for Men, From Backyard to Black Tie

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.

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.

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.

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.

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.

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.

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.

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?