- Dress boots for men can be costly but, with proper care, think of a good pair as an investment that could last for a very long time.
- Thursday Boot Co.'s Wingtip heads the top of the list with its outstanding quality and value.
Dress boots may be the most versatile footwear out there. They look as good with an old pair of jeans as they do with a suit and give off a slightly rugged, masculine vibe without being in your face about it. A dress boot, unlike a hiker or a work boot, doesn't typically have a fat outsole, so you're not going to go hiking in the Sierras or do construction in these, but they're sturdy enough to handle rain and snow, especially compared to, say, a pair of Italian loafers. While dress boots tend to be a bit pricey, they're three-season footwear and with proper care, will last you for years. Additionally, since these styles are pretty timeless you won't look outdated down the road.
We've put together a list of our favorite quality men's dress boots under $500. I've either personally tested these or in some cases have relied on customer and other professional reviews.
Our overall best dress boot is the Thursday Boot Co. Wingtip. I've been road testing a pair for two years and they pretty much look as good today as they did when I unboxed them in 2017 (and I'm notoriously hard on footwear). Here at Business Insider, 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 the best men's leather dress boots you can buy for under $500:
- Best men's leather dress boots under $500 overall: Thursday Boot Co. Wingtip
- Best for commuters: Wolf & Shepherd Breakaway Boot
- Best for a dressy occasion: Allen Edmonds Sullivan Street Dress Boot
- Best affordable men's leather boots: New Republic Huxley Chelsea Boot
- Best for standing out in a crowd: Grenson Fred Commando Soles
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