Like so many valiant pieces of menswear before it, the dress boot has had to fight for its spot at the top of the sartorial food chain. What’s that? Don’t think the best dress boots for men deserve that designation and aren’t willing to be convinced otherwise?
We’ll wait while you see yourself out…
Everyone else, prepare for enlightenment. Worn properly, dress boots can elevate an outfit without skimping on the utility. And given their unique ability to straddle the line between formal and casual, you can lace them up for almost any occasion. Work: check. Wedding season: bring it on. Steakhouse with the investors: we’ve got you covered.
So here they are—our picks for the top 12 men’s dress boots across a range of categories. And before you ask, yes, one of them is dairy farming. (No, one of them is not dairy farming.)
The best dress boots for men don’t have to be the most expensive, the flashiest, or have the most groundbreaking design. All they have to be is comfortable, versatile, and offered at a price you’re comfortable with. Though there’s no such thing as a one-size-fits-all scenario, we think Thursday’s Wingtip might come close.
Goodyear Welt construction, shock absorbing insoles, a wingtip brogue pattern, and the sturdy good looks of a proper boot come together to make your feet the talk of the occasion. Which occasion? All of them. Except for maybe yard work—there’s a dad shoe for that.
Material: Leather | Sizes Available: 6 – 16 | Colors available: Black, Brown | Formality: Formal, Casual | Style: Ankle
Strapping on a pair of cowboy boots and confidently sauntering into a wedding doesn’t have to be an expert-level move. All you need is the right pair from the right manufacturer. And, of course, enough confidence to pull off the cowboy look when the day comes.
Enter the Majestic Roper. Lucchese has been manufacturing boots in Texas since the late 1800s. They’ve been worn by presidents, celebrities, and men who like to add a touch of covert badassery to their outfits. Oh hey, that’s you. Supple goat leather and intricate stitching give this timeless pair of dress boots a versatile and rugged look.
Material: Goat Leather | Sizes Available: 7 – 15 | Colors available: Black, Tobacco | Formality: Casual | Style: Calf
You’d be hard-pressed to find a footwear specimen more versatile than the Chelsea boot. And though they come in endless styles and colors, this black pair from A Day’s March is ready for any occasion you can throw at it.
A throughline of Italian Mastrotto leather is only one feature that makes this one of the best dress boots. A Day’s March is also committed to the environment and spares no expense to reduce waste and maintain a small footprint. And did we mention it’ll make you look like the crown prince of Chelsea boots? If not… it’ll make you look like the crown prince of Chelsea boots.
Material: Leather | Sizes Available: 7 – 11 | Colors available: Black | Formality: Casual, Cocktail | Style: Ankle
You’d never know these best dress boots for men aren’t a regular pair of Oxfords. A row of hand-punched brogueing along the toe cap is part of what lends the Elliot Balmoral this covert look. And that vibe continues up the ankle with simplistic stitching across calfskin leather sourced from a prized Italian tannery.
If you’re not planning on wearing these with jeans or chinos in addition to formal attire, you may as well opt for actual Oxfords (yes, they’re that close in aesthetics). Otherwise, it doesn’t get more adaptable than these lace-ups from Beckett Simonon.
Material: Leather | Sizes Available: 7 – 14 | Colors available: Black, Brown | Formality: Casual, Formal | Style: Ankle
Steeped in American tradition, Wolverine’s 1000 Mile Classic is the epitome of form meeting function. The handsome and timeless silhouette is bolstered by a Goodyear Welt construction and sturdy leather from Chicago’s storied Horween tannery. To give you just a taste of the love poured into these beauties, each pair is handmade in the US by over 80 shoemakers.
Though you could just as comfortably work the land for decades in this rugged pair of dress boots for men, you’re probably better off pairing them with chinos for an upscale casual dinner or jeans for a Sunday brewery session with friends. But you already knew that—we were just looking for an excuse to say “work the land.”
Material: Horween Leather | Sizes Available: 7 – 14 | Colors available: Black, Brown | Formality: Casual | Style: Ankle
Business below, party up top. That’s how one might describe this handsome pair of dress boots for men, especially if one were completely out of other things to say. Still, though, Myrqvist has outdone itself with this exquisite footwear specimen with a 360-degree Goodyear storm welt to keep your feet toasty and dry.
Like most dress boots worth their salt, this pair exudes elegance and sophistication below the cuff, but they’re all about utility just beneath the surface.
Material: Leather | Sizes Available: 7 – 12.5 | Colors available: Brown | Formality: Formal, Casual | Style: Ankle
Ah, the wingtip. Timeless bastion of horse track buffoonery, steakhouse negotiations, and 19th hole world-domination plotting. Right? Wrong. The venerable wingtip was meant to be peacocked around in whichever scenario you feel could use a good peacocking.
And with that in mind, we turn our attention to Johnston & Murphy’s XC Flex Cody boot with its inside zipper, suede-and-leather construction, and sheepskin lining for maximum breathability. This entrant to our list of best dress boots for men is formal, but not too formal. Casual, but not too casual. And most importantly, super comfortable, thanks to its memory foam insole.
Material: Leather, Suede | Sizes Available: 8 – 13 | Colors available: Black, Brown | Formality: Formal, Casual | Style: Ankle
Chukkas, by their very design and nature, are comfortable. But these chukkas take things to a whole other level. A podiatrist designed the footbed specifically to provide orthotic support for those who may suffer from foot pain. Does this mean you have to walk with a cane and be named Albert? Nope. Just a regular, active guy who’s prone to foot aggravations just like everyone else.
If you love the look of these cozy, comfortable shoes but don’t necessarily need the extra support, the footbeds are removable. As for where you’re wearing them, think summer evenings on some sort of windswept patio. String lights may be involved. Probably a glass of gin. Definitely a date.
Or you could just wear them to work.
Material: Suede | Sizes Available: 7 – 11.5 | Colors available: Black, Tan, Brown | Formality: Casual | Style: Ankle
Velasca went all-in with the construction of the Armiro boot. Its calf leather lining envelops your feet with warmth and makes these venerable foot sheaths perfect for year-round use. The calfskin leather is treated in a way that encourages breathability, and the handsome buckle helps elevate your look without skimping on edge.
All of this translates to a cozy, cloudlike boot that should be considered a staple in any man’s closet. Pair it with tailored-look jeans to put that buckle on center stage, or hide it under suit pants only to dazzle your onlookers when it’s time for an effortless leg cross. Everyone loves a good effortless leg cross.
Material: Calf Leather | Sizes Available: 5 – 14 | Colors available: Black, Brown | Formality: Casual, Formal | Style: Ankle
Taft has your funky, unorthodox, bohemian vibes covered with most of its boots, but especially with the Jack Boot in the Florence colorway. The colorful flower motif is eye-catching but not so much as to read tacky—especially if correctly complemented and partially concealed by a neutral trouser leg.
And lest you think these are all about catching compliments (though that’s certainly an attractive side-effect), Taft has built the Jack Boot to last. One potential drawback is this pair’s tendency to bleed in wet conditions, so no puddle jumping while these quirky specimens are laced up.
Material: Cotton Twill, Leather | Sizes Available: 6 – 15 | Colors available: Multicolor, Brown | Formality: Casual | Style: Ankle
When the snow is falling, but the formal show must go on (we’re looking at you, winter destination weddings and holiday office parties), it’s time to break out the big guns. Or the… winter dress boots. You get it.
Here to help you get it even more is Blundstone’s #1900 dress boots. Expect the same tough-as-hell performance as you would from any other Blundstone Chelsea, but with the added benefits of head-turning good looks and being ready for whatever your winter nights have in store.
Are these the most formal winter boots you’ve ever seen? Certainly not. Do you get a pass because snow is wet and your feet have feelings too? Damn right you do.
Material: Leather | Sizes Available: 6 – 13 | Colors available: Black, Brown | Formality: Formal, Casual | Style: Ankle
A form and function staple, the Chelsea boot is available in every style, color, and budget. If the latter is a consideration, look no further than Shoe the Bear’s Dev Chelsea boot. Handmade in Portugal, it checks all the sturdy construction and comfort boxes while maintaining a handsome silhouette.
Team this pair of men’s dress boots up with a casual summer suit or with a pair of broken-in jeans on a crisp fall day. We’ll also accept “literally any other type of day.”
Material: Suede | Sizes Available: 7 – 15 | Colors available: Black, Brown | Formality: Casual | Style: Ankle
What To Look For When Searching For The Best Dress Boots For Men
The best dress boots for men come in a variety of materials, from suede to leather and all points between. If you’re looking for a casual everyday boot that can moonlight as formal under the right circumstances, you can’t go wrong with a leather upper in a neutral color. But if the boot section of your closet runs deep, there’s no shortage of ways to diversify your footwear portfolio.
Not all dress boots have to be formal. That said, you’ll want to look for boots casual enough to wear with jeans or chinos but formal enough to suit up with. Most excellent dress boots for men look like traditional dress shoes when the shafts are covered by pant legs. A solid rule of thumb: business below, party up top.
As with any footwear, you’ll be in a world of hurt if your boots don’t fit properly. Most manufacturers will have a size guide or, at the very least, a description of whether the boots fit true to size or run small or large. Measure your feet and compare the measurements with the company’s online recommendations if you’re unable to try boots on in person.
How you choose to dress up or dress down your boots is completely up to you. Generally, though, you’ll want to weigh the overall look and feel of the boots against the clothes you pair them with. If it’s a more serious dress boot that screams formality, a tailored suit is always a winner. Boots that lean more casual can be worn with anything from jeans to chinos.
There are several ways to lace your dress boots that give a professional appearance—one of the most popular being the cross-bar method. To achieve this clean look, start by putting the laces through the bottom eyelets. From there, cross them as you normally would, only below the upper itself. This allows for one clean row of horizontal laces up the length of the boot.
Not only can you wear dress boots with a suit, but it’s also a fantastic look that we highly encourage. And bonus: You don’t need a lot of sartorial wherewithal to pull it off. Just make sure you match the formality of the boot with the formality of the suit.
No two feet are alike, so what’s comfortable for one man might be torture for another. That said, there’s a universal truth or two. Generally speaking, the softer the upper (be it a supple leather or cushy suede), the more comfortable your feet will be. Some dress boots for men even come with orthotic inserts like the Chase chukkas from Vionic.