The Chelsea Boot Is the King of Trend-Proof Footwear

Best All-Weather Chelsea Boots: Blundstone 500 Chelsea Boots

Some Chelsea boots lean heavily into their rockstar appeal, while others skew utilitarian, expressly designed to protect you from the elements. Then there, however, are the rare pairs that gracefully straddle the line between. Enter the other Australian boot: Blundstone. Those tough leather uppers might not be monsoon-ready, but on days when you just need to jump a few puddles en route to work, the whole package is the slickest way to ensure your socks stay dry without compromising your fit.

Tired Bushwick memes aside, Blunnies are truly good looking boots built like a tank. They can take a real whooping and still show up for their 5 a.m. shift behind the espresso machine, ready for more. They’re a boot you don’t have to feel precious about, and the de facto kicks to wear when the weather forecast just says “shitty.” They look great with vintage jeans, a pair of Dickies, cargo pants, and chinos—though, in our humble opinion, they don’t belong anywhere with a dress code (explicit or implied).

Best Lug-Sole Chelsea Boots: Red Wing 3192 Suede Chelsea Boots

If you think of Red Wing, it’s the brand’s iconic 6-inch moc toe boots you’re probably imagining. But the Minnesotan boot makers can do more than turn out jobsite-endorsed footwear. Introduced in the 1990s, Red Wing’s Chelseas were made for ranchers who wanted something durable enough for the farm, but easy enough to nap in. They’re a happy middle ground between a high-shine European Chelsea like the R.M. Williams and the woodsy Blundstones.

That means you get Goodyear-welted construction and built-to-stroll rubber outsoles topped by Hawthorne Muleskinner roughout suede. The texture is “rugged handyman,” but the dusty tan and dark brown color can hold down a coffee date-worthy fit. White tees and white jeans? Sure. Nice pants and a knit sweater or polo? Absolutely. Wranglers and a Stetson. Of course.

Best Suede Chelsea Boots: Morjas The Chelsea Boot

Morjas is best known for loafers worn by everyone from Wall Street bros to Greenpoint baristas. Now the Swedish shoemakers are coming for your ankles with a Chelsea boot. If you’ve already graduated from Chelsea Boots 101 by having a classic black or brown calf-leather pair in your closet, consider these brown suede beauties for next semester.

They’re fully leather-lined but require absolutely zero break-in time, thanks to a studded rubber sole that feels like walking on a cloud… if clouds had traction. Style-wise, they walk the line (pun intended) between office-ready and weekend cool—equally dialed in when paired with a crisp white dress shirt beneath unforgiving Monday-morning fluorescents or some linen pants while you sip a doppia espresso in Florence.

Best Chelsea Boots for Fashion Guys: Saint Laurent Vadim Polished-Leather Chelsea Boots

Hedi Slimane’s legacy at Saint Laurent was all skinny jeans, razor-sharp suits, and rockstar Chelsea boots. The look he cooked up over a decade ago has come back again, with guys dubbing themselves Hedi Boys looking to recreate the magic. One glance at boots like these, and you understand why. A leading man gleam and a stacked Cuban heel mean these boots by themselves could headline Coachella. The only update: a very right-now edginess (literally) at the toe. Whether or not the rumored skinny jeans comeback arrives, these are the boots to wear when you want all eyes on you.

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