My Alden Roy boots are probably my favorite piece of footwear that I own.

For a long time, I was on a quest to find the ultimate brown plain-toe boot: not overly dressy but not un-dressy, goes with everything, displays a perfectly simple shape without any excess panels or stitching, sneakily cool. A boot which, if you look at it with an untrained eye, just looks like a regular old boot—but upon further inspection is actually well beyond that, maybe even exceptional. Something legitimately timeless. A boot I’d be desperate to pull back on every 48 hours, after it got a day off from the last wear. Something, honestly, that was just really effing cool, without trying too hard.

I found exactly what I was seeking with the Roy, the signature Alden makeup from Context Clothing in Madison, Wisconsin—initially somewhat randomly, on Instagram. I obsessed over the scant worn photos I found on Google Images, displaying the a beautiful patina on the brown Chromexcel leather (no need to get cute or creative when seeking a boot designed for timelessness, right?).

I pulled the trigger. I was not disappointed—not in the least. They immediately took that every-other-day job, and accompanied me on basically every trip I took, at one point doing 10 miles a day in Tokyo.

There was one thing, though. The crepe rubber sole was superbly comfortable and cushiony, but the tradeoff for that was rapid wear. I walk a ton (even when I’m not in Tokyo!), and before long I needed to pick other boots and bench the Roys if there was a chance of even slight rain—on the wrong surface they just didn’t have the traction I needed. So I started thinking about an outsole with a bit more grip, and definitely something that offered the promise of longer life as I walked 4, 5, 6 miles a day, almost every day.

The answer: Dainite. British outfit Harbaro Rubber’s signature product, Dainite soles offered the durability, low-ish profile, and traction and grip that I was seeking.


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Alden Roy Plain Toe Boot With Dainite Outsole

When I floated the idea out there, some people thought me mad. “ALDEN ON DAINITE?! I think you might be mad,” was an actual comment from an actual person. But after speaking to the good people at B. Nelson on 55th St. in Manhattan, I thought became convinced of two things: the idea was right, and they were the ones to pull it off. B Nelson probably does the most Alden re-soles/re-builds/re-everythings of any shop in New York (they also have all the stock Alden soles, which most shops don’t, if you’re looking for that).

The leather midsole and heel stack were a must, and we kept the original prestitched reverse welt that gives the boot so much character. The stitching is largely good and true, and I opted for a slight stain on the threads—I saw them in pure white at first and honestly it was kind of cool, but I decided it contrasted too oddly the rest of the three-year old, lovably beaten boots.

All Aldens are built with an impressive solidity—but these things, suddenly, are tanks. Everything adds up to them being significantly heavier than the crepe. So they’re more substantial, but still never a chore, something I’m dragging around behind me. They’ve lost that crepe bounce, but I knew what I was getting myself into on that front. They are ready to clobber whatever comes at them, and seem prepared to be with me for years to come.

The only thing I’m considering to get them all the way home is doing a further antiquing on the midsole and heel stack. Some days I like the contrast pop they give off; others I wish everything was a little darker, a little more uniform.

Now to figure out what to do with my resole-desperate Indy boots

Alden Roy Plain Toe Boot With Dainite Outsole

Alden Roy Plain Toe Boot With Dainite Outsole

Alden Roy Plain Toe Boot With Dainite Outsole

Alden Roy Plain Toe Boot With Dainite Outsole