Well Worn

The Most Stylish Men We Know Share Their Favorite Boots

October 19, 2019 Style : Shoes By Photo by Chandler Bondurant
Purchasing products through our links may earn us a portion of the sale, which supports our editorial team’s mission. Learn more here.

Much of the time, a quality pair of boots is both the literal and figurative foundation of any man’s wardrobe. Built to stand up to years of wear, they have the potential to outlast most of the other items in a guy’s closet. Because there are numerous brands making first-rate boots, one must make a conscious long-term decision when investing in a new pair. Over years of wear, these investments become highly personal, forming to the wearer’s feet, displaying well-earned creases and aged hues.

To hear the stories behind some well-loved boots, we reached out to some of the most stylish guys we know and asked them to share their favorite boots. The styles and stories vary as much as personalities we surveyed, but every pick exhibits top-tier features built to stand the test of time.

Todd Snyder, Designer


Vintage Red Wing 877 Irish Setter Boots: “I probably have over 15 pairs of boots, so it’s hard to pick just one. I guess my favorite boots are my Red Wing 877 Irish Setters circa 1970. I found them vintage in a RRL store approximately 15 years ago and they fit me perfectly. I have a size 13 foot and I can never find vintage anything that comes close to fitting me, so I jumped on them. They had the best patina and were in great condition so the $500 price tag seemed like a steal. They are totally worth it.

To me, Red Wing invented the work-boot and are still doing it the way they did back in the day — made in the USA with great quality and comfort. These boots are the reason that I wanted to collaborate with the brand in the first place. I get so many compliments from the Red Wing workers when I visit their factory in Minnesota. I travel there once a year to discuss the future collabs and work with their design team. Everyone there is very proud of what they do. I cherish these boots because they look cool, but they also are legit (looks like I wore the heck out them, but took very good care of them). I should give thanks to the guy who broke them in for all of those years! Thank you, sir.”

Antonio Ciongoli, Designer of 18 East


Clarks x Lemaire Redland Boots: “I’ve been wearing Clarks since I was a kid and I can’t think of boots that are more comfortable. I love these Redlands because while the crepe runner’s toe makes them look like a Wallabee/late-’90s skate shoe mash-up, they’re actually a discontinued silhouette from the ’60s. When Lemaire brought them back last winter, I bought two pairs just to be sure I was covered should the silhouette disappear again. Afterward, I was happy to discover that Padmore and Barnes — the original Clarks manufacturer in Ireland — never stopped making them. I’m glad to know they’ve got me for life.”

Jake Mueser, Owner of J. Mueser Bespoke


J.FitzPatrick Alki Chelsea Boot: “I’ve had these black Chelsea boots for years now. They were the first pair of shoes I got from my friend Justin Fitzpatrick, founder of J.FitzPatrick Footwear. My style has always been a mix of classic and more relaxed. I tend to wear jeans with a nice jacket so a pair of good Chelsea boots is perfect. Alternatively, they also work when I wear with a suit and tie. The construction on these is amazing, they are Goodyear welted and hand-finished. I am having a new pair made in espresso suede, probably less versatile but excited to add to the collection!”

Donnell Baldwin, Chief Stylist of Mr. Baldwin Style


RRL Engineer Boots: “I fell in love with these engineer boots while working at Ralph Lauren in the Vintage and Antiques Division years ago. My boss would wear engineer boots with army green cargo pants, a gray vintage tee and an assortment of silver and turquoise jewelry. There was something easy about it all — an effortless cool that was undeniable. I knew then that I had to get a pair of these boots and that they’d give me that effortless, authentic style I always admired. These boots have been with me for seven years now and keep getting better as time goes on.”

50 Best Boots for Men

From rugged engineer boots to office-friendly brogues, these are the pairs you should invest in. Read the Story

Note: Purchasing products through our links may earn us a portion of the sale, which supports our editorial team’s mission. Learn more here.

John Zientek

John Zientek is Gear Patrol's style editor and in-house guitar authority. He grew up on the West Coast.

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