All the Boots Our Editor-in-Chief Swears By

Okay, so right off the bat I’m lying to you guys. I don’t own these boots, but I very much would like to. The reason I included them here is that I currently find myself preferring slightly dressier options when it comes to chukkas. Just last night, I was talking with some folks in the office about how the standard desert boot silhouette — whether you’re talking about the classic Clarks version, the J.Crew MacAlister or the Todd Snyder Nomad — is feeling a bit stale right now. And I say this as a person who’s had at least one pair of those in my rotation for probably 25 years, so perhaps it’s just a classic case of me getting sick of myself. Regardless, a nice, structured pair of chukkas like these from Alden, with some crisp, dark denim, an OCBD and a tweed blazer is a timeless, put-together look. If these are too pricey for you, there’s also this handsome option from Beckett Simonon.

Alright, so this is really my sweet spot when it comes to boots, to the extent that I had a very difficult time figuring out which one to feature. The Iron Ranger has been a go-to for me for years. I own them in both brown and black, and I feel like they most accurately capture my whole vibe and work best with many of the other staples in my wardrobe. A very, very close second, though, is the Red Wing Moc Toe, which features a chunkier silhouette and the immediately recognizable white soul. They’re pretty heavily associated with the whole workwear trend from the early 2010s (and I guess also again right now?), but you’ll have a hard time convincing me they’re anything but classic.

Admittedly not a boot I get a whole lot of use out of — it should come as little surprise to hear that we’re not exactly suited up every day at IH HQ — but I’m glad to have them. My father, a devotee of traditional conservative menswear, swore by the Allen Edmonds Park Avenue Cap-Toe Oxford, so I felt obligated to add a pair to my collection when he died a few years ago. I’ve since added the boot version as well, and I think it looks extremely sharp on the rare occasion that I do wear a suit.

Are there hiking boots out there that are better equipped to handle challenging terrain and inclement weather? Very much so, yes. But do I ever truly find myself dealing with challenging terrain and inclement weather? Reader, I do not. So for my purposes, the Merrell Moab 3 is more than sufficient, and despite their being a little suburban dad-coded, I actually really like the way they look. They’re also extremely comfortable. If you are actually a person who goes hiking and needs some real performance from your boots, you’ve got a million options from La Sportiva, Salomon, Danner and the like. I’ve got the Danner Light Khakis, which are awesome, though they are anything but light.

I know I said I don’t really fuck with Chelsea boots, and that technically these qualify as such, but in my mind, given their rugged durability and more substantial presence on the foot, they’re such an outlier in the category that I think they basically deserve their own. I have complicated feelings about how Blundstones work and what kind of leg opening on your pants is best suited for them, but for me, I wear them in the rain and with slightly wider-leg pants than I normally do. Pretty sure I’m overthinking the whole situation because literally everyone else on the planet looks awesome in them regardless of the situation. You should definitely have a pair of these.

Remember when it used to snow? I’ve had these in my closet for two years, and I think I’ve worn them once. But look how cool they are! A classic Sorel style, featuring an aggressively lugged sole for real traction, plus a quilted top that makes it a little easier to fit them under a pair of pants. I hope to wear them again some day.

Full disclosure: I also don’t own these, but I’m about to add them to my Christmas list because, yes, I am a 46-year-old man who still makes a Christmas list. These beautiful leather lace-ups from Mr Porter’s house brand would be an excellent choice for anyone who wants a polished but not stuffy look for the office or for a night out on the town. As evidenced by the model on the site, they look great with a pair of jeans, and I suspect they’d do just fine being dressed up a little more as well.