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Welcome to the Esquire Endorsement. Heavily researched. Thoroughly vetted. These picks are the best way to spend your hard-earned cash.


New York City eats away at my boots. Typically, I wear my cowboy boots with everything—suits, jeans, even a tuxedo. All I do is give a high shine to my black snip-toe Luccheses. I do love the classic dress-shoe brands—Alden, all the English ones, Berluti—but like a sleazy Texas politician, I take a sick pride in always wearing my boots. This city doesn’t take kindly to that. In the winter, the roads and sidewalks get salted to hell. When it rains, puddles are (like everything here, I assume) carcinogenic. It’s a bad environment for leather soles and lemonwood pegs.

So this winter I had to get a pair of rubber soles, something I could wear with everything. I looked to one of the world’s other great cowboy cultures, Australia. I got a menswear favorite, the R.M. Williams Crafstman boots with the comfort rubber sole. Over this winter, I realized these boots could replace almost every other shoe I own. I’ll never give up my cowboy boots, but I think most men (women too) who read this magazine could give up 90 percent of their shoes for this pair of boots. So stop—think about every shoe you own. I’ll tell you how an R.M. Williams Craftsman will replace it.

Close-up of a black leather boot with branded pull tabs.

Florence Sullivan

They’re Rugged

I’m sure you’ve heard about how this was one of New York’s snowiest winters in some time. (This city likes to talk about itself.) For the majority of this rugged winter, I was wearing these boots. I would change into a pair of beat-up pull-on work boots only to dig out the car, or a pair of sneakers to get in a workout. Otherwise, I lived in these R.M. Williams boots. So long as I didn’t step through a shin-deep puddle or snow bank, I was totally fine. I wore wool boot socks when it was below freezing, $4 Uniqlo socks when it wasn’t. They never required breaking in, and no matter how I wore them, no matter how many miles I put on them, they never aggravated my feet. They are true Outback boots at the end of the day.

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But They Can Dress Up

But you could say that rugged stuff about a pair of Blundstones, and I’m not a huge fan of Blundstones. As I said, the key to good boots is that they can dress up just as they dress down. I might get crucified by Styleforum types for this, but these boots are acceptable for everything that’s not a tuxedo. They are, at least, not the most egregious thing you can see with a suit. For me, if you wear trousers of a proper length, you won’t see all that much of the elastic ankle. At this point, they act like a pair of dress boots.

I also love the toe—what I, knowing about cowboy boots, would call a French toe—that slightly squared-off shape. It gives it some elegance, more so than a regular Chelsea boot’s rounded toe. So long as you keep shoe trees in them and give them the occasional shine, they’ll absolutely look better than the dress sneakers other people are wearing. And compared with the guys in oxfords, you’ll look a lot more interesting, a little bit rockstar.

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Black leather Chelsea boot with elastic sides

Florence Sullivan

Most Importantly, You Buy Them for Life

Three things work in favor of this boot as a buy-for-life item. First, the R.M. Williams comfort soles are no joke. I find them less about comfort (leather soles are plenty comfortable) and more about durability. Over a few months of hard use—snow, rain, flights, and hikes through city and country—there’s virtually no sign of wear. Other first-hand reviews on the Internet will show people saying the same thing over the course of half a decade of hard work. Second, the primary seam is on the back of the boot. The entire upper is a single-cut piece of yearling calfskin. It’s rugged, breaks in beautifully, and won’t rub you weird. Finally, and this is related to the quality of the leather, you can repair them endlessly. R.M. Williams will do it for you, but if shipping them to Australia once a decade for a resole proves too time-consuming, any local cobbler can make quick work of it. Yes, you pay $600 now, but you’ve then got a pair of beaters you can wear for life.

Will I trade my cowboy boots for something from the Outback? No, but R.M. Williams gives me the same thing I like from my ’boy boots—endless wearability, a somewhat rugged look—in a shape I think is more friendly for the majority of people. If you have ever looked at your shoe rack and seen the sneakers everyone else owns, dress shoes you never wear, and rain boots that kill your feet, throw them all out right now. A pair of R.M. Williams is all you actually need.

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Photographs by Florence Sullivan

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