Staff Picks: Our Favorite Leather Boots

If you looked under the table at one of Outside’s morning news meetings, you’d notice a lot of leather boots on the feet of our male editors. Part of it has to do with style. Boots, jeans, and a flannel are sort of the office uniform. (It’s embarrassing how often we look alike.) Part of it also has to do with convenience. We’re a little lazy, and leather boots can be dirty and scuffed up and still look good. No single brand or style is most popular. Instead, everyone has their own favorite pair.

Red Wing Iron Ranger Boots ($320)

These rugged yet sleek leather boots were originally designed for iron miners in northern Minnesota. Which is to say: they’re built to withstand a lot of abuse. My pair, unsurprisingly, took a while to break in, but after a few weeks, the thick Amber Harness leather began to mold to my foot, leaving me with a comfortable and elegant boot that I’ve had for four years and will likely have for many more. My only complaint: the cork soles have no tread, and thus walking on snow or ice is a bit precarious. (Red Wing has since released a model with a grippy Vibram mini-lug outsole.) But I can’t really complain—it forces me to engage my small stabilizing muscles while walking, which is a good thing. Always be working, amirite? —Wes Judd, online fitness editor

Wolverine Original 1,000 Mile Boots ($360)

There’s a reason I wear Wolverine boots: they’re made in Michigan, and I can remember (or think I remember) both of my grandfathers having a pair. The 1,000 Mile boots are the most comfortable shoes I’ve ever had besides my house slippers. The leather bottoms make them slippery as hell in the winter, but from March to December, I wear these to work, on dog walks up the arroyo, and even on those rare occasions when I put on a tie. I’ve had them for two years and have already put about a few hundred miles on them. I imagine I’ll be hitting the 1,000-mile mark years from now, and they’ll still look good. —Jonah Ogles, articles editor

Clarks Desert Boots ($130)

I bought these boots to keep my feet dry in the snow and mud, and because they fit well. They used to be nice—like fancy nice. I could have worn them to a job interview if I wanted. But I didn’t like them as much back then. Now, they’re better. I’d still wear them to a job interview, though—no one wants a job that looks down on a pair of old boots. —Matt Skenazy, senior editor

Wolverine Evans Boots ($400)

These boots stand out among the other choices here because the color is more red clay than traditional brown leather. The more I wear them, the better they look, with the Horween leather aging like a patina. The aggressive Vibram sole can be overkill in downtown Santa Fe, where it doesn’t snow a ton, but I’m always glad to have those lugs when I’m at home in Maine after a big snowstorm. I can’t imagine wearing the Evans on a trail since they’re significantly heavier than my normal hikers, but they are great for around town and in the Outside office. —Ben Fox, editorial assistant

Frye Tyler Lace Up ($320)

Frye has been around since 1863, so the company knows a little something about making boots. I like the Tylers for their versatility: I’ve worn them to work in Santa Fe and out to dinner in New York and never felt like they’re out of place. Plus, the vintage Italian leather is incredibly soft and comfortable, and the rubber insets on the sole have just enough grip on snow and ice. —Bryan Rogala, video production manager