Well Worn

The Boots Our Staff Can’t Live Without


October 18, 2019 Style By Photo by Chandler Bondurant
Editor’s Note: This post has been updated with new picks for 2019. You can find last year’s picks on here.

Every day, our staff filters through hundreds, if not thousands, of pieces of gear, whether in-hand or in the form of press releases, articles, lookbooks and more. We survey a wide array of products from tech gear to booze to motorcycles, but the common thread between every desk is a love of boots. From our office in New York to the streets of cities around the world, we’ve put a staggering array of boots to the test, each employee gravitating towards something unique. While no way definitive, these are a few of the boots our staff can’t live without.

White’s 350 Cutter Boots

“White’s was founded in 1853 in West Virginia and relocated to Spokane, Washington in 1915. A favorite of loggers for more than a century, White’s also makes boots for smokejumpers battling forest fires across the West. Between world wars, loggers asked Otto White for a lower-profile version of the boots they wore in the forests, so he took a chainsaw to the shaft of a 10-inch boot, essentially creating the 350 Cutter. The lace-to-toe version was created by White’s now-CEO Eric Kinney in the ‘90s, but still features handsewn stitchdown construction and the all-leather arch the brand is known for. It may be the most hard-wearing and comfortable boot you can buy.” — John Zientek, Associate Editor

Quoddy Kennebec Chukka

“Part of me thinks I moved from Charleston to New York just so I could have more months a year to wear boots. I needed a boot for the transitional months; something that wouldn’t make my feet sweat but still felt cozy enough on brisker mornings. These Quoddys were a gift to myself for dragging my life up here and do just that. I bought them at a second-hand store because moving (and living) here is very expensive and I’d heard they’re made very well. I heard correctly.” — Will Price, Assistant Editor

Thursday Boot Co. President

“I have more hiking and tactical boots than I know what to do with but have never owned a dressier pair. I picked up these Thursday Boot Company Presidents two years ago in brown because Red Wing wanted [much more] money for their equivalents — plus these come in wide sizes, (which I need). The brown color lets me reminisce about my brief airborne days without walking around in real jump boots, like a shmuck. They feature a Goodyear welt, an antimicrobial insole, and full glove leather interior lining, and if you condition them properly, they should last for years. Just be forewarned — the first few months of ownership are painful.” — Oren Hartov, Associate Editor

Red Wing for J.Crew 9143 Plantation Chukka Boot

“I bought these Red Wings about five or six years ago, but they ended up gravitating to the back of my closet for most of that time. The crepe sole got worn down fast and left my dogs barking and slipping in any kind of weather. Last summer I dusted them off and had a chunky commando sole added. After that, I could hardly take them off my feet. Comfortable, rugged, and not too shabby looking, I wear them with lots of varying wales of corduroy for a certain WASP-y collegiate vibe or maybe an off duty gamekeeper on a large estate. I love it.” — Charles McFarlane, Content Producer, Gear Patrol Studios

To Boot New York Stallworth Boot

“I first got my hands on a pair of To Boot loafers in 2013, and over the past few years have built a small collection from the catalog. These boots have been wearable since Day One and the quality is truly remarkable, earning more and more patina with every clunk into the Subway stairs. Dark denim and all sorts of other pants pair nicely and they can be dressed up and down for the office or the bar.” — Tim Murray, Account Executive, Brand Partnerships

Red Wing Heritage Iron Ranger Boots

“For about a month, I was positive I’d gone too small. After decades of tearing through pair after pair of roomy size 12 Vans, I knew that good boots that could last me much longer should start out feeling a little less spacious. Still, I held my breath as I slid into a snug pair of 10.5 Redwing Iron Rangers in charcoal. What followed was several weeks of tightness, a few strange blisters, some strategic sock decisions, and more than a little self-doubt, but my feet and the leather were eventually able to come to an agreement. Two years on (and mercifully wider than they were at the start), these beautiful boots are not just the most comfortable footwear I own, but maybe the most comfortable I think I’ve ever worn. And I’ll love them forever because we got here together.” — Eric Limer, Editor

Vans Sk8-Hi MTE

“No one will mistake a Vans Sk8-Hi for something like Red Wings or Fryes, but just about everyone owns a pair because the vulcanized outsole is comfortable and they can go with just about anything. Wearing chunky boots all winter trudging through sleet and snow gets tiresome, so I find myself wearing these Vans more often than not. The weather-resistant leather uppers allow them to be wiped clean and my feet are always dry and warm thanks to the heat retention layer. This pair doesn’t have a sherpa lining, so I can even wear them on rainy days in the fall and spring months without my feet getting too warm.” — Ryan Brower, Project Coordinator, Editorial Operations

Yuketen Maine Guide Boots

“My Yuketen Maine Guide boots are easily the most precious pair of boots I’ve ever owned. These boots are a genuine moccasin construction but with a Japanese personality. They are handsewn in Maine and pay tribute to classic techniques used to make boots in the early settlement days of New England. Being hand sewn makes them feel a little different on the feet, way more comfortable than a machine-stitched shoe. The craftsmanship is second to none — which sorta justifies the high cost of them. These boots will outlive me.” — Hunter D. Kelley, Associate Designer

Alden x Need Supply Co. Shields Boot

“I was hankering for a pair of Alden Indy boots for a while when I came across these Alden x Need Supply boots. About 80 percent of my wardrobe is some shade of blue, so it just made sense. (I avoid wearing these with an overly blue outfit lest I look like an unofficial member of Blue Man Group.) The Chromexcel leather started off navy but has faded into a worn-out blue. A waterproof pre-stitched reverse welt means I don’t have to hop over sewer water puddles on the way to the office, and the crepe sole provides comfort, especially when I’m running late to work. I have a fairly laissez-faire attitude towards shoe care, but the result is a beautifully broken-in pair of boots.” — Tyler Chin, Editorial Associate, Editorial Operations

Red Wing Heritage Clara Boots

“These are the boots I donned for a family trip to Africa in 2018 — and every time I pull them on, I reminisce about it. We started in Johannesburg, then spent a handful of days on a wild game reserve near Kruger National Park in South Africa. Our daily game drives began at 4 AM, which were well worth it for all the zebras, giraffes and elephants we saw, plus the cheetahs and lions.

“Seeing the animals meandering around the desert landscape quickly put into perspective just how large they truly are. While that may sound absurd — have you ever really thought about how giant an elephant is? Large enough to flip over an open-air jeep, that’s for sure. Every morning, I pulled on the Clara boots, climbed into the back of the 4×4 and never thought twice about them, which is to say, they did their job perfectly.” — Meg Lappe, Editorial Coordinator

Eastland Sherman 1955 Boots

“I discovered a shoebox with two left foot boots in it at a retailer. I was totally into them, so I helped the employees scour the store for the next 45 minutes until I discovered the two right foot boots and reunited the pairs. They were so grateful they provided me with a hefty discount, on top of a coupon and a birthday promo code I already came armed with. At the end of the day, I walked out with a pair of iconic boots for a small fraction of the original cost and used the savings to resole them with some heavy Vibram tread. Since then, they’ve slushed through NYC snow and also been paired with slacks, a tie and blazer.” — Kyle Snarr, Head of Marketing

Thursday Boot Co. Duchess Chelsea Boots

“Full disclosure: I was gifted these a few years ago by the Thursday Boots team. They soon won my trust — functionally and sartorially — as I noticed that every time I searched my closet for the right pair of footwear to plus up a casual outfit, these were the boots I picked. They also happen to be surprisingly comfortable, which I learned in quite a few sprints to Penn Station when running to catch a train. I love to throw them on with jeans, or even leggings or joggers, to make an otherwise low-lift outfit feel put-together.” — Caitlyn Shaw, Consumer Marketing Manager

Wolverine Jenson Waterproof Boots

“Style-conscious motorcyclists face an eternal conundrum: the best riding boots don’t look so great off the bike, and the most stylish boots don’t fare so well on it. I grappled with this reality for some time, until I discovered Wolverine’s Jenson boots. From the moment I laced them up, they were super comfortable and sharp, the cap toe adding an unmistakable touch of class. Then I rode with them, and they only rose in my esteem. The Gore-tex lining keeps my feet warm and dry, while the classic rubber sole (replicated from a 1950s boot) provides life-saving grip on sometimes sketchy New York City streets. I generally pair with button-down shirts and jeans — and a temperamental Bonneville T-100 Black, of course.” — Steve Mazzucchi, Editor

Danner Forest Heights II

“This pair of Danners were my first real leather boots. Before that, I had no idea of what it meant to have shoes age with you. Every nick and imperfection in the leather reminds me of the miles walked. Some of my favorite memories with them were days spent outside building sets or mucking through the snow. Also getting them resoled when I moved to New York was a moment of re-birth for my beloved boots.” — Joe Tornatzky, Art Director

Red Wing Heritage x Todd Snyder Moc-Toe Boots

“The Todd Snyder Red Wing Moc Toes are the first leather boots I’ve actually worn since the obligatory physical labor boots (also Redwings) I wore at one of my first jobs, and they’re totally different. I would describe the leather’s soft-but-firm feel as similar to that of a baseball glove — but on your feet. They’re surprisingly light and comfortable, quick to break in, and the combination of leather and suede gives them a refined feel. Leather laces are a nice touch too.” — Zen Love, Associate Staff Writer

The 50 Best Boots to Buy

This guide to the best boots for men covers nine different categories, including work boots, Chelseas, chukkas and more. Read the Story
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