The 9 Best Leather Dress Boots for Men in 2023, All Under $500

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Leather dress boots may be the most versatile footwear out there. They give off a slightly rugged vibe without being over the top, and can help elevate a simple look or give a suit a little more panache. And while the best leather dress boots can get pricey, they’re three-season footwear (depending on where you live) and with proper care, will last you for years.

We’ve put together a list of our favorite quality men’s dress boots for under $500. I’ve either tested these, or in some cases have relied on customer and other professional reviews. And since these styles are pretty timeless, you won’t look outdated down the road.

Our overall best dress boot is the Thursday Boot Co. Wingtip. I’ve been road-testing a pair for six years and except for some minimal wear, they pretty much look as good today as they did when I unboxed them in 2017 (and I’m notoriously hard on footwear). We’ve praised this company in the past, and continue to do so because of their boots’ formidable construction, price point, looks, and quality.

Here are our picks for the best leather dress boots for men:

Best overall: Thursday Boot Co. Wingtip – See at Thursday Boot Co.
The Thursday Boot Co. Wingtip is a great looking, durable boot and an outstanding value at under $250.

Best budget: Florsheim Midtown Plain Toe – See at Florsheim Shoe Company
The Florsheim MIdtown Plain Toe is a classic zipper boot from an American heritage brand at a great price.

Best for comfort: Taft Mack – See at Taft
Gorgeous Italian leather full-brogue boots that break in easily and are supremely comfortable.

Best waterproof: Beckett Simonon Silva Boots – See at Beckett Simonon
A fully waterproof and handsome Chelsea boot that can take on the nastiest weather.

Best cowboy: Tecovas Dean Boot – See at Tecovas
Stunning, versatile, and impeccably made.

Best Chelsea: Ace Marks Troy – See at Ace Marks
Made in Italy using old-world techniques and exceptional materials at a reasonable price.

Best Moc Toe: Grant Stone Field Boot – See at Grant Stone
Ruggedly handsome and able to elevate your everyday style.

Best vegan leather: Nae Lore Vegan Derby Boots – See at Nae Vegan Shoes
A dress boot free of any animal products that looks like a million bucks. 

Best combat: John Fluevog Castellano – See at John Fluevog
An upscale leather and suede take on the combat boot with striking details.

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