The best men’s leather dress boots you can buy for under $500

  • 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 Additionally, since these styles are pretty timeless you won’t look outdated down the road.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:


The best men’s leather dress boots for under $500 overall

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Thursday Boot Co.

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

Thursday Boot Co., a direct-to-consumer brand launched in 2014 by Nolan Walsh and Connor Wilson, is bringing top-quality, handcrafted boots to market at a reasonable price point (from $149 to $265). Their Wingtip boot ($220) is both stunning and solidly built. There’s a lot of rich broguing and other detailing and it features Goodyear-welt construction. This labor-intensive method of attaching the outsole to the upper makes for durable, water-resistant footwear that can easily be resoled down the line.

There are four color choices – brandy, caramel, black, and my favorite, a rich brown that is almost an oxblood, in a double-tanned leather that has a deep, glowing shine. The interior has full glove leather lining and there’s a cork-bed midsole, which conforms to the shape of your foot over time, to make for a fit that feels custom made.

These boots broke in easily and pretty quickly took on the shape of my feet. Two years in, they remain very comfortable. The uppers have stayed looking great with a relatively lax maintenance schedule that mainly involves cleaning and polishing them somewhere in the range of three times a season – they’re taking on a nice patina. The midsoles are showing wear but not unduly so.

These boots tend to run about a half-size larger than what you would wear in a sneaker. They’re a little heavier than some of my other dress boots, although that hasn’t kept me from wearing them a lot each year. They’ve gotten me through New York winters and soggy springs without leaving my socks feeling like sponges, and I’ve worn them on long city treks (5 miles or more) without discomfort.

Pros: Durable, handsome, very reasonably priced

Cons: A bit heavy (may not be the best choice if you do a lot of walking)


The best for commuters

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Wolf & Shepard

Wolf & Shepherd’s beautiful Breakaway Boots are made of full-grain Italian calfskin and are so light I wore them jogging. Seriously.

I’d been hearing about this brand for a few years before getting a pair. The company’s claim to fame is its hybridization of dress and running shoes. Wolf & Shepherd was founded in 2014 by Justin Schneider, a former track and field star at Notre Dame who later designed running shoes for Adidas.

The boots are made in Portugal of full-grain Italian calfskin and come in black, chili (a reddish-brown), and honey (these last two colors have burnished toes). With its high shine and cap toe, these boots pair extremely well with a suit, but I’ve also styled them with black jeans, a T-shirt, and a Western snap shirt and they looked great.

The boots have a good bit of padding, including on the tongue and heel, while still maintaining a sleek profile. They incorporate memory foam and high-density ethylene-vinyl acetate (EVA), more commonly found in running shoes than in dress boots, as well as a carbon-fiber shank for stability. The boots have a lot of stretch and are lined in buttery soft sheepskin. They quickly conformed to my foot and there wasn’t a break-in period to speak of.

For this story I threw them on and went for a run to see if the hype lived up to the reality. Although the experience was slightly embarrassing – apparently no one’s seen a guy jogging in dress boots before – it was not physically uncomfortable. Only my pride hurt from the weird looks of the passerby. The mile-long jog was downright enjoyable. I wouldn’t make a habit of it, though, since they’re $395 dress boots.

Unlike most of the footwear in this guide, the Breakaway is also more like a running shoe in that the sole is glued on rather than attached via a Goodyear welt. Boot mavens tend to have a problem with a glued sole because it’s harder to resole them, among other reasons. That being said, the boot has been specifically designed so that it can be resoled by the company (for $80, a decent price, actually), but not by a cobbler. I’ve read that these boots run small but the fit was spot on for me. If you have a wide foot you may be out of luck; they don’t currently offer the boot in wide sizes.

Pros: Super lightweight and comfortable, nicely padded while maintaining a sleek profile, looks great with a suit

Cons: A bit on the pricier side, can’t be resoled by a cobbler, limited sizing for guys with wide feet


The best for a dressy occasion

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Allen Edmonds

Allen Edmonds Sullivan Street Dress Boots are distinctive and handsome, incorporating two types of leather, yet still tough and long-wearing.

Allen Edmonds is an old-school American-made brand based in Port Washington, Wisconsin that was founded in the 1920s and continues to craft outstanding footwear. Their Sullivan Street dress boots are made from two types of leather, a soft and lustrous vegano calfskin and a pebbled leather that gives these boots subtle, unique styles. They come in black or coffee (brown).

The addition of the cap toe gives it a dressier feel that deserves to be paired with a nice suit for those special occasions where you want to impress, be it a date or a business meeting. They probably wouldn’t work with a tux, but everything else is on the table. At $445 you’re probably going to want to wear them more than a few times a year. Thankfully, they’re versatile enough to wear with business casual or even dressed-down with a nice pair of chinos and a button-down shirt for a night out with friends.

Allen Edmonds is known for its craftsmanship and the Sullivan stays true to form with Dainite rubber soles that provide grip and stability, a cork-based midsole that conforms to your foot, and Goodyear-welt construction. The Sullivan Dress Boots received positive reviews from the Bespoke Unit and Stridewise blogs.

Pros: Beautiful and distinctive, well-made, can be paired with a nice suit or casual attire

Cons: Priced at the high-end


The best on a budget

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New Republic

The New Republic Huxley Chelsea boot is as stylish as brands that charge twice the price.

Chelsea boots have been all the rage of late and New Republic’s version, the Huxley, will keep you looking stylish without draining your wallet. They look as good as higher-priced boots, thanks to their narrow profile and nicely tapered toe. They have a natural crepe outsole and a padded insole for comfort, a warm tan-colored leather upper, and leather lining and footbed.

New Republic, a direct-to-consumer brand started by fashion designer Mark McNairy in 2016, has been racking up accolades here at Business Insider, as well as in New York Magazine, GQ, and Esquire. New Republic has also been getting love from customers who have been specifically happy with the company’s Chelsea boots.

“For this price point, this is the only game in town,” wrote one verified customer on Amazon. “They fit like a glove, the crepe sole is spongy and soft, and the leather-lined interior shapes to your foot, making it feel like a custom boot on the fourth or fifth wear.”

Like most Chelsea boots with a crepe sole, the outsole can’t easily be replaced because it’s glued on. I spoke to a service rep at the company who told me a cobbler may be able to change out the sole.

Pros: Great looking boot for an unbeatable price

Cons: The soles are glued on and can’t easily be resoled


The best for standing out in a crowd

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Zappos

Grenson’s Fred wingtip brogues with commando soles are a truly unique boot, with beautiful details and a bit of edge.

Grenson is a British heritage brand that’s been around since the 1860s and continues to deliver. The company perennially appears in “must-have” lists in places like GQ and Esquire. Guys Style Guide called the Grenson Fred commando sole “truly sensational,” and we agree.

The Grenson Fred is part of the company’s G: Two line. While some of Grenson’s boots run upward of $600, these come in at less than $350 (a bit more for the dark brown version) but still retain the brand’s standards. The G: Two line is hand-assembled in India, with the leather selected in the company’s UK factory and the lasts (the form over which a boot is constructed) made in the UK.

The Fred comes in black, tan, and dark brown (the latter two are hand-painted, giving them a deep, lustrous color). The chunky commando sole gives the boots heft, stability, and traction, making them great for bad weather. You’ll also literally stand out in a crowd because these boots will make you a bit taller than if you were wearing typical dress shoes. They’re Goodyear welted for better waterproofing and easier resoling.

Because of the commando sole, you’re probably not going to want to wear these with a business suit, though they would work well with tweed. These are perfect for both business casual and smart casual and look amazing dressed down with a pair of jeans.

Pros: Unique style, beautifully detailed, great for winter

Cons: The commando sole isn’t for everyone and is less dressy than other styles


What else we considered

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Johnston & Murphy

There are many great boots out there that are nearly as good as these choices. Here are two that almost made the cut.

Johnston & Murphy Conard Wingtip

I own several pairs of Johnston & Murphy shoes and boots and really like the brand. The company has been around since 1850 and they offer a variety of great looking and very comfortable footwear at a good price. The boots typically run under $200. The Conard Wingtip is a great example. It has a 5-star rating based on 50 reviews on the company’s website and comes in at $179. It didn’t make the cut based on my experience with a pair of the company’s Merrit wingtip boots. The stitching began to come out on one of the boots about four months after I got them, requiring repairs. The company does have a 90-day return policy for defects but I missed the window by just a few weeks. My other purchases from the company have been issue free and I will continue to buy from the brand.

Wolverine 1000 Mile

The Wolverine 1000 Mile boot was another contender. They’re well-constructed American-made heritage boots. They have a 4-star rating based on 253 reviews on the Wolverine website. In the end, they didn’t make the cut because for the $385 price tag, they’re just not that versatile. They’re not quite dressy enough to be worn with a suit or business casual. They are the perfect boots for a weekend look, dressed down with jeans or chinos, a collared shirt and blazer or shawl-collar sweater.