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The 21 Best Men’s Dress Shoes for Every Occasion

Photo: Thursday Boot Co.

You can wear the nicest suit in the world, but if your dress shoes are lacking, then your entire wardrobe goes out the window. Dress shoes are the ultimate sartorial punctuation point, shouldering the gargantuan responsibility of tying an outfit together. If you have a stellar pair of dress shoes, your formal attire will certainly pop more. While there is a trove of incredible men’s dress shoes on the market to wear, sifting through them can be incredibly overwhelming.

Thankfully, we’re here to help you in your quest for the perfect dress shoe. We’ve compiled a guide to the best dress shoes for men that you can wear and have broken them down into seven major styles to fit your sensibilities. Not all dress shoes are created equal, but all of these chic shoes will do you right.

The Brogue

Detailed Beauty

The brogue is similar in design to a standard Oxford shoe, although it features a distinct perforated pattern. Broguing is the term used to describe the pattern of holes that marks the outer leather of these shoes. Originally, these perforations allowed water to escape the sopping shoes of the Irish and Scottish folks who wore them, although nowadays, the broguing pattern is purely aesthetic.

Cole Haan Modern Classics Wingtip

A style icon and household name, Cole Haan has been making accessible, fashionable footwear for decades. While it’s difficult to pick out just one of the brand’s offerings, its Modern Classic Wingtips are simply too stylish to exclude. These resplendent, Oxford-style shoes feature full-grain leather uppers with genuine leather lining for added comfort. An EVA footbed provides stability and shock absorption while the salpa welt detailing and intricate broguing offer more style points than you can count. If you’re in the market for a modern interpretation of a timeless classic, you can’t go wrong with these brogues.

Purchase: $300

Trickers Bourton Derby Brogue

Trickers has been one of the premier shoemakers in the world for almost two centuries. The British brand’s phenomenal footwear has captured the hearts and feet of all who have worn them, and its Bourton Derby Brogues exemplify Tricker’s master craftsmanship. These dapper shoes feature a chocolate leather suede construction and are pinked and brogued by hand, which is evident given the precision of the broguing. The true genius of these shoes, however, is that they toe the line between formal and casual, so you can either dress these up for a formal event or dress them down for a night out on the town. Regardless, you’re going to look criminally good while doing so.

Purchase: $505

Brunello Cucinelli Suede Wingtip Brogues

Brunello Cucinelli is a sartorial sorcerer who designs luxury garments that ooze style. Seriously, just about everything this man designs is immaculate. Case and point: his Suede Wingtip Brogues. This beautiful amalgamation of contemporary style and timeless design perfectly encapsulates the brilliance of Cucinelli’s design language. The shoes are made of suede leather and feature a leather lining for enhanced comfort. Their rubber-trimmed soles provide a neutral canvas to either dress up or rock the relaxed look. No matter how you wear these shoes, you’re guaranteed to have the best footwear in the entire room.

Purchase: $1,095

The Chelsea Boot

Where Military Meets Style

Chelsea boots are snug ankle boots featuring stretchy elastic side panels. Aside from their minimalist design and silhouette, another hallmark of the Chelsea is its pull tabs for easy on and off. They got their name due to their popularity in Chelsea, a chic area of London.

Charles Tyrwhitt Suede Chelsea Boots

Charles Tyrwhitt is a well-respected British label that makes impeccably good-looking formalwear that’s accessibly priced. The brand sticks to the classics and executes them as well as any luxury brand out there. Its Suede Chelsea Boots are an example of the timeless design and modern methods Tyrwhitt uses to make its garments. These beautiful boots are made from premium calf leather and feature a Goodyear-welted sole that enhances their longevity and durability. For superior comfort and a relaxed fit, the designers at Tyrwhitt incorporated insulating cork filler between the insole and the sole to mold to the shape of your foot as you wear them.

Purchase: $249

Belstaff Longton Leather Chelsea Boots

Belstaff is an iconic shoemaker, having made some of the best shoes in the industry for almost 100 years. While the brand makes incredible outerwear, its Longton Leather Chelsea Boots are simply sensational. The boots have the same rugged elegance that made Belstaff iconic, however, their refined, minimalistic silhouette elevates them to match with almost any wardrobe. They feature a calf leather construction that’s supple yet durable, as well as timeless Chelsea characteristics like front and back pull tabs and elasticated gusset sides. If you’re looking for a style workhorse that can go with pretty much anything, you can’t go wrong with these.

Purchase: $395

Tom Ford Robert Polished-Leather Chelsea Boots

Tom Ford is another style wizard who seemingly can’t help but make incredible clothing. The man is one of the most iconic designers of the modern era, so of course, his Robert Polished-Leather Chelsea Boots are going to make it on this list. We’d be remiss to exclude them. Their premium calf polished-leather construction is so chic that these boots literally gleam with style. For easy access, the boots feature elasticated gusset sides and a subtle pull-tab that doesn’t interrupt the gorgeous, streamlined silhouette of these boots. Leave it to Tom Ford to find a way to elevate a timeless staple like the Chelsea.

Purchase: $1,490

The Chukka

Minimalistic Chic

Chukkas are ankle-high boots that are made with two whole pieces of leather, have two (occasionally three) eyelets, and often feature thin laces. They’re a fantastic and versatile boot that thrives in upscale casual to semi-formal settings.

Thursday Boot Company Scout Chukka

If Thursday Boot Co. isn’t a brand you frequent, then it should be. The Big Apple brand has mastered the craft of leatherworking and has a wide range of phenomenal shoes to show for it. In particular, its Scout Chukkas are some of the suavest you’ll find on the market. They feature a genuine leather construction, a lined supple glove leather interior, and Poron antimicrobial insoles that absorb shock as you walk and keep the stink at bay. Design-wise, their leather construction elevates the streamlined, minimalistic silhouette of the chukka for an elevated casual look. These chukkas will never prove you wrong.

Purchase: $149

Clarks Desert Boot

Clarks’ Desert Boot burst onto the scene in 1950 and has only gotten more popular and appreciated as time has passed. The iconic chukka has made its way around the world and launched Clarks’ reputation into the sartorial stratosphere. Its upper features a premium leather construction which is complemented by the minimalist lace fastenings. A streamlined design and understated stitching empower this amazing boot to transcend eras or seasons, while its suede tags remind us of the brand that started it all.

Purchase: $230

Crockett & Jones Coniston Boot

Crockett & Jones is a footwear institution and makes some of the most dapper shoes on the planet. The Northampton staple has been producing masterpieces since its 1879 inception, and its Coniston Boot is proof that the brand’s design language has aged like fine wine. These boots are effortlessly stylish, made from a rugged yet sophisticated scotch grain leather, and constructed with Dainite rubber soles for comfort and a storm welt for durability. Their lace-up design offers a snug and secure fit while their pull-tab provides easy accessibility. These are dress boots you simply can’t pass up.

Purchase: $725

The Dress Boot

Rugged Elegance

Dress boots are pretty amorphous to define given how wide-ranging of a category they are. In this case, we’re looking for boots that are taller than chukkas, feature lace-up fronts, and sport a durable, rugged look.

Dr. Martens Vegan 1460

It’s hard to find a brand that’s as iconic as Dac Martens. The Doctor has long been a streetwear staple as well as a go-to bootmaker for many in the high-fashion space, which makes sense due to the shoes’ classic design elements. The Vegan 1460 adds a sustainable layer to the already head-turningly stylish look of Doc Martens’ famous boots. We see all the iconic elements that make the 1460: its eight eyelets, grooved sides, a heel-loop, the signature yellow stitching, and an air-cushioned sole. Add in the Goodyear welt stitching for durability and a 100% vegan construction, and you have one of the best boots out there.

Purchase: $101+

Thursday Boot Company Wingtip Boots

A footwear company so nice, we had to mention it twice. When “boot” is in the name of your company, you almost have to make one of the best pairs of boots in the footwear space, and Thursday Boot Co. did precisely that with its resplendent pair of wingtip boots. Their smooth and pebbled leather construction provides the perfect smooth canvas for the intricate broguing pattern to pop while the chiseled toe adds a little textural flair as a punctuation point. Their Goodyear welt makes the boots easy to resole and also provides a decent level of water resistance. For comfort, the Wingtips feature cork-bed midsoles while their studded rubber outsoles provide excellent grip in the elements.

Purchase: $235

Wolverine Original 1000 Mile Boot

Whoever said that dress boots can’t be rugged clearly never owned a pair of Wolverines. The American standout has been making classic shoes for over a century, and if the timelessness and undying popularity of its shoes keep at its pace, it’ll most likely be around in another century. Wolverine introduced the original 1000 Mile Boot in 1914, its modern contemporaries are nearly identical. They sport the same rough-and-tumble design and Horween leather construction, but they also come with some modern upgrades. Their Goodyear Welt construction provides durability and flexibility while the Vibram heel makes them comfortable and stable enough to walk 1,000 miles comfortably.

Purchase: $385

The Loafer

Slip Into Style

The loafer is a laceless shoe that slips on and off the foot. While many loafers have tassels and penny keepers, hence the term penny loafers, the main criteria for loafers is that they are slip-on shoes without laces.

Vinny’s Townee Patent Leather Penny Loafers

Vinny’s is a stalwart label that makes a stellar pair of penny loafers. These shoes are as timeless as timeless gets, which makes perfect sense given Vinny’s penchant for making classic gems. Its Townee Patent Leather Penny Loafers are a work of beauty, sporting a gorgeous black patent-leather construction that shines like a diamond. Their traditional penny straps, signature engraved logos, and hard-wearing soles provide the perfect design accents and durability to keep this sleek pair of loafers in your rotation for years.

Purchase: $285

Viberg Slipper

Viberg, the British Columbia standout, makes some of the most handsome shoes you can buy, and while the brand call its loafers “slippers,” we’d argue they satisfy all the pertinent criteria to be called loafers. Confining the style of these loafers to just your home is heretical. Inspired from vintage travel slippers from Viberg’s archives, the Slipper has a timeless design and calf suede construction that will up the style quotient of any wardrobe with which you pair them. If there ever were a perfect autumnal loafer, it would be Viberg’s Slipper.

Purchase: $620

Fear of God Leather Penny Loafers

We know, Fear of God probably isn’t the first name you think of when you hear “penny loafers,” but one look at its masterfully designed penny loafers is all it will take to convince you that it’s really a premium penny loafer brand disguised as a fashion-forward streetwear label. These penny loafers feature the timeless, understated silhouette of the classic penny loafer, however, they have a sleeker, more contemporary design for a shot of modernity. They’re made of gorgeous calf lining, with comfy leather soles that will give you all the more reason never to take these bad boys off.

Purchase: $695

The Monk Strap

Buckle Up, Buckaroo

A monk strap is another style of a laceless dress shoe, however, rather than strictly being a slip-on shoe, they feature one or two clasps to secure the shoe to your foot. They are particularly in vogue nowadays due to their versatility.

La Milano Double Monk Strap

Finding an accessibly priced pair of dress shoes that aren’t cheaply made can be a herculean task, thankfully, brands like La Milano are here to provide big quality, bigger style, and even bigger value. Its Double Monk Strap is simple, well-made, and oh-so-stylish, featuring a genuine Argentinian leather upper with a rich color due to the company’s special paint and brush technology. Aside from looking handsome as all get-out, these monk straps also boast a memory foam insole for all-day comfort. If you’re looking to turn heads on a budget, you definitely can’t go wrong with these shoes.

Purchase: $70

Paul Stuart Giordano Monk Strap Shoe

Anyone who denies the beauty and trendiness of the monk strap need only see Paul Stuart’s Giordano Monk Strap Shoe. The stalwart designer makes a slew of head-turning shoes, but we’re particularly fond of these impeccable monk straps. These Italian-made works of art feature a dapper single strap for minimal interruptions of their silhouette and maximum style points. Featuring a premium calf leather construction that is augmented by the shoes’ Goodyear Welted soles, these understated shoes are the perfect accent piece for any formalwear with which they’re paired.

Purchase: $995

John Lobb William Double Sole Suede Shoes

With a rich British history dating back to the 1870s, John Lobb is a heritage brand that every appreciator of fine footwear should know, and the William Double Sole Suede Shoes only provide more evidence of that. These gorgeous shoes feature a double monk strap, an elegant suede leather construction, and double soles for enhanced comfort. From a design standpoint, they drip with style. All it takes to see the premium quality of these shoes is a quick gander, which is also all you’ll need to fall in love with them.

Purchase: $1,495

The Oxford

Old Faithful

Oxfords are your classic dress shoes, often characterized by their closed lacing. This design allows for the shoe to have a slimmer, more elegant profile.

Allen Edmonds Carlyle

Shoe brands don’t get a lot more recognizable than Allen Edmonds. The Wisconsin brand has been a staple in the men’s footwear space since its 1922 inception. It’s almost impossible to pick just one standout shoe of the brand to pick, but we’re particularly partial to its Carlyle Oxford. These dapper shoes are about as classic as can be, featuring a premium European calfskin leather construction that’s built on a 360 Goodyear Bench Welt for unrivaled comfort and stability. They sport an elegant and sleek silhouette that can dress up business attire or complement formalwear.

Purchase: $300+

Alden Straight Tip Dress Oxfords

Speaking of iconic shoe brands, it’s hard to find a more recognizable and respected brand in the space than Alden. The Massachusetts shoe staple has been churning out premium shoes since 1884, which has led it to become a shining example of American craftsmanship. Its Straight Tip Dress Oxfords are a fan-favorite that boasts a gorgeous calfskin leather construction, dovetailed heels, and vegetable-tanned leather insoles that are as sustainable as they are comfortable. They feature a classic and elegant design that thrives in formal settings and a sleek silhouette that’s as timeless as the brand that makes them.

Purchase: $603

Viberg Bastion Oxford

Rounding out our list of the most dapper dress shoes on the market is Viberg’s devilishly handsome Oxford. This particular shoe draws inspiration from Viberg’s funky Oxfords of the 1960s and sports a Black Horsebutt construction that hails from Comipel, Italy. The Bastion features a low-profile silhouette and elongated toe to fit virtually any foot comfortably, however, the designers at Viberg updated it to have a trimmed heel and waist for a cleaner, more streamlined design. If you’re looking to strut your stuff in a suit or semi-formal slacks, these are the shoes for you.

Purchase: $730

The Best Men’s Suits Under $1,000

Now that you’ve figured out your dress shoes, take a gander at our guide of the best men’s suits under $1,000 to complete your Sunday-best wardrobe.