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The Three Kinds of Boot

Bootspic via Ethan Desu

It’s a safe bet you’ll be kicking through some leaves in the near future, and you’re going to want to be dressed for it.

So we thought we’d break down the vagaries of rugged footwear into three distinct categories. Each one has its own brands and its own rules—from the rugged Red Wing to the gentlemanly cordovan equivalent—and we’ve got a favorite in each category.

Ladies and gentlemen... the three types of boot.

Red Wing

The Work Boot The classic indestructible boot. These have been all over lately, but for good reason. If you want to protect your feet against absolutely anything that comes your way—including lava and gunfire—this is the gold standard. There are some pretty handsome versions out there, including this one from the Brothers Bray, but the best is still... The Pick: The Red Wing 8-Inch Moc. The Reason: A high ankle, a classic sole and some of the toughest leather known to man.


The Mountain BootThis is what you want when you’re kicking through leaves in their natural habitat—which means it’s lighter and more water-resistant. It takes a bit of panache to pull off outside of a camping trip, but we’re sure you’re up to the challenge. The workwear gold standard is Yuketen or, for a cheaper version, Bean Boots —but for our money, the circle of trendiness has turned to something a bit more European.The Pick: Merrell Wilderness Canyon Boots. The Reason: Vibram-soled, waterproof, ultra-light. Have fun with the laces.


The City BootAs you may have noticed, we haven’t gotten to the strolling-through-the-city boot quite yet. It’s because we’re saving the best for last. These are the winterized form of classic cap-toes and brogues, from shops like Alden and Grenson. (The latter brand makes a handsome Balmoral, by the way.) Because of Mr. McNairy, they’re as likely to have Vibram soles as leather, but there’s no mistaking the leather uppers. Just for God’s sake, don’t take them into the woods... or wear them with a suit.The Pick: Alden Shell Cordovan Tanker. The Reason: The picture says it all.