Guys either love dress shoes or can’t stand them and never want to wear them again. We understand and feel for each party.
Dress shoe haters will eventually have to attend a wedding, work conference, funeral, or the big ball. Something that will call for any of the best black dress shoes. The dress shoe lovers have so many damn options to choose from that it’s hard to know what’s the best.
If you’re here, it’s because you want the best black dress shoes, and we get that. We like having the best of everything option. You could peruse the internet and read reviews for hours on end, or you could just check out our guide because we did the boring, research-ey part for you.
Check out the guide and decide for yourself. You can shower us with praise later.
When choosing the best black dress shoes, it’s always good to go with a modern classic; the Cap-toe Oxford. Unless you’re rocking a tuxedo, the formality of classic Oxfords can be unnecessary for most gatherings. The toe-cap adds a little bit of blue-collar flair, so they’re still a beautiful formal dress shoe, but you won’t look overdressed at your job’s Christmas party.
This Comovita masterpiece is handcrafted from Italian leather and made to order in Spain. You’ll be happy to know top-tier comfort and durability didn’t take a backseat to style. If you had to choose one dress shoe for the rest of your life, this would be your best bet. You may have guessed already, but that’s why they’re our overall pick.
Material: Italian Leather | Sizes Available: EU 35 – 48 | Style: Cap-toe Oxford
Not everyone loves ultra-formal gatherings. If you’re the type who’s eager to leave as soon as you get there, maybe this fabulous pair of loafers will chill you out a little.
Thanks to their lace-free nature, the penny loafer is one of those dress shoes that feels more casual than formal. Don’t worry, though, because these are just as acceptable as Oxfords or brogues in most situations. The lace-free look is just too sleek to hate on.
Toss these on and be comfortable. Let your anxieties go. If it’s a fancy place, there’s probably at least some good food somewhere.
Material: Leather | Sizes Available: US 6 – 15 | Style: Penny Loafer
Oliver Cabell and Uncrate came together to create the sexiest pair of driving loafers you’ve ever seen. These casual dress shoes scream good taste. If you’re looking for something semi-formal you can chill in all day and hit the bar at night, you might want to give these beauties a shot.
These loafers also make driving so much better (hence the name). Thanks to their pebbled sole, i.e., all those weird little bumps, it’s easier than ever to grip the peddles on your car. They also have an Arneflex microfoam footbed for maximized dress shoe comfort and ultimate loafing. Your feet will be happy cruising to a cocktail party or bullshitting with buds for hours.
Material: Italian Suede | Sizes Available: US 6 – 15 | Style: Driving Loafer
Cole Haan is an expert in footwear innovation, and it shows in the Howland Penny Loafers. These add contemporary moccasin stitching to the old classic to elevate this preppy favorite into something new. Somewhere between a driving loafer and a traditional penny loafer, the Howland sits near the new peak of penny loafer design.
You already know Cole Haan makes some of the best black dress shoes on Amazon, so maybe it’s time to check them out if you haven’t. This pair comes with the wraparound pebbled heel to make driving a breeze and the classic penny loafer strap with a slight divot to add personal flair.
Material: Leather | Sizes Available: US 7 – 13 | Style: Penny Loafer
The best black dress shoes don’t always have to be worn to an office or a formal gathering. If they’re the right style, they’ll fit in anywhere. And desert boots are the most versatile dress shoes you need in your life. A true footwear jack-of-all-trades. Good desert boots will be admired at the company lunch and then kill at the weekend festival.
Crown Northampton’s desert boot is the cream of the crop. We chose the Kudu suede because it’s a little less formal than the shinier, squeaky leather choices. That way, they won’t look as gnarly when they’ve been kicking around Burning Man for a few days. That is if Burning Man is still open to normal people and not just influencers.
Material: Kudu Suede | Sizes Available: UK 3 – 12 | Style: Desert Boot
They’re not technically shoes, but Chelsea boots are still an active part of the dress shoe family. Beloved because they’re just as versatile as they are sexy, a good pair of Chelsea boots will last years and look awesome everywhere you take them.
Artisan Labs put together the best pair of Italian leather, blake-stitched Chelsea boots we’ve ever seen. The company says they’re made in “the greatest hub of Italian shoemakers” in the world, and it’s totally believable.
And we’ll save you a trip to google; the mystery shoemaker hub is called Le Marche. You’re welcome.
Material: Italian Leather | Sizes Available: EU 39 – 46 | Style: Chelsea Boots
“Formal dress shoes” might sound redundant for the uninitiated, but trust us, it makes sense. All the best black dress shoes are formal, yes, but you can’t just wear a pair of chukkas with a tux. Well, you can wear anything you want, we just wouldn’t recommend it. You get the idea.
If you’re going to a gathering that requires the fanciest of the fancy attire, you want classic Oxfords (or opera pumps for braver guys). Don’t get a wingtip, brogue, or cap-toe. Just go for the tried-and-true classic. Trust Fashionbeans and MYRQVIST on this one; you won’t regret it.
Material: French Leather | Sizes Available: US 7 – 12.5 | Style: Classic Oxford
We have no idea how to pronounce the name, but that doesn’t mean this isn’t one of the best black dress shoes you can buy. MYRQVIST proved again why they’re among the most masterful leatherworkers in the world with this pair of Oxfords. It has everything that makes a cap-toe Oxford unique and cranks the quality to the max.
This pair comes with MYRQVIST’s signature french leather (who isn’t tired of seeing “Italian leather”) from the world-famous Du Puy tannery. Slap on some high-quality heel caps and cork filling to add supportive comfort, and you’ve got the best pair of Oxfords you will ever buy. Don’t be surprised if you stick with these till you’re an old-timer.
Material: French Leather | Sizes Available: US 5 – 13.5 | Style: Cap-toe Oxford
Just because a pair of shoes is affordable doesn’t mean they suck. Exhibit A: The Dream Pairs collection from Bruno Marc. They have the same elegant look you’d expect from an excellent pair of Oxfords without the high price tag to go with it. The vegan leather doesn’t detract a bit. Some people even prefer it over the real deal.
All that, and they actually feel pretty nice on your feet. Did we mention they have 4.5 stars with over 9K 5-star reviews? You don’t get to be the #1 best-selling Oxford on Amazon for no reason.
Material: Vegan Leather | Sizes Available: US 6.5 – 15 (wide available) | Style: Wingtip
There aren’t a ton of options for dress shoes with an authentic matte finish. If you’ve decided that’s the look you want, Jousen has you covered. Don’t let the low price fool you; the quality is quite the opposite. They might not be a well-known brand, but plenty of men love these shoes, and we can’t blame them.
All the regular features are here: two-piece construction, four shoelace eyelets, and the signature Oxford two-piece stitching. They’re also synthetic leather, which is probably why they feel a little more matte than genuine leather options.
Material: Synthetic Leather | Sizes Available: US 7 – 15 | Style: Classic Oxford
If you don’t want to sacrifice comfort just to sit in a business meeting, Cole Haan designed these for you. It’s not obvious just by looking at them, but these really are the most comfortable of the best black dress shoes in this guide. And we don’t take that lightly. After all, comfy living is happy living.
Cole Haan calls these the go-to wingtips for good reason: they’re so damn comfortable you won’t want to wear anything else. You might even love them enough to grab a second pair (or a fifth) and start a collection. Don’t say we didn’t warn you.
Material: Waterproof Leather | Sizes Available: US 7 – 13 | Style: Wingtip Oxford
Boat loafers live in a much different world than regular old loafers. This pair is more suited for yacht club stylings and grip better on slippery docks. Wear with a pair of no-show socks, 5 to 7-inch inseam shorts, and a pastel blue or red polo to achieve a perfectly bold dock-side summer look.
Oliver Cabell’s boat loafers ooze so much style and class that onlookers will definitely be taking notes. And don’t be surprised if people ask where you got them. Considering they’re 100% hand-stitched Italian leather, it would be weirder if you didn’t get compliments on some of the best black dress shoes.
Material: Italian Leather, Rubber Outsole | Sizes Available: US 5 – 15 | Style: Boat Loafer
Shopping for the best black dress shoes with wide feet can suck. Like, a lot. Luckily, Crown Northampton allows you to request wide sizes of their incredible Regent Wholecut shoe when you’re ordering. That way, you’ll be spared the heartbreak of discovering the shoes you love refuse to fit right.
Since there’s no stitching on the outside, they stretch and mold to a wide foot much easier than thicker, more robust styles. And that doesn’t mean they’re delicate by any means. They just aren’t as firm as many other styles. You can rejoice now, fellow wide-footed men.
Material: Italian Leather | Sizes Available: UK 3 -13 | Style: Penny Loafer
He’s not exactly the pinnacle of ethics and morality, but Hugh Hefner definitely knew how to dress luxuriously. He always had his signature pieces of clothing—the smoking jacket, the silk trousers, and of course, the iconic black velvet loafers.
If you’re trying to conjure up the stylings of old Hef, you’re 100 percent going to need a pair of slip-on velvet loafers, and Steve Madden has you covered. These don’t cost thousands like Hefner’s did, but they’re still one of the best black dress shoes.
Just don’t expect girls to flock to you because of your new silk jacket and velvet shoes unless you’re also rich as shit.
Material: Velvet | Sizes Available: US 7 – 13 | Style: Loafer
“Dress sneakers” might sound like an oxymoron but don’t be fooled; it’s definitely a thing. We wouldn’t wear them to the met gala or anything, but the proper sneakers will look pretty damn dapper in most semi-formal and formal settings. And black leather doubles down on that. These shoes are guaranteed to catch some stares from admirers.
Uniform Series does a great job of taking the classic sneaker and adding a modern twist with their Series 8. The triple black takes a timeless black tennis shoe shell and adds high-grade Italian leather and a bombastic black sole that elevates this pair from a vintage love letter to a contemporary hit.
Material: Italian Leather | Sizes Available: US 8-13 | Style: Sneaker
If you’re looking for an Oxford with a strong, modern look, this offering from Cole Haan might be your new favorite. The Zerogrande Oxford is a slick, unique pair of the best black dress shoes that will please anyone getting tired of their classic formal wear. These are snazzy enough to wear to a management meeting and get positive attention from stuffy higher-ups but not avant-garde enough to annoy them.
Cole Haan pulled off a dress shoe that’s simultaneously classy and futuristic—equal parts star trek and dancing with the stars. Pick these up if you think you might want to try something a little more unique than a “regular” dress shoe.
Material: Leather | Sizes Available: US 7 – 16 | Style: Oxford (sort of)
The look hasn’t changed much since the 1800s, and that’s because it hasn’t had to. The popularity decrease can be attributed to men’s aversion to wearing anything “feminine” over the past century.
Don’t let companies trick you by pawning off their patent leather loafers as opera pumps. As far as this style is concerned, no bow = a no go. Thanks to the tight fit, thin sole, and insanely comfortable quilted satin lining, they’re so perfect for dancing it’s like they were made for it (fun fact: they were).
If you want the epitome of class and style for your next gala or wedding, these are the best black dress shoes to turn heads. Get ready for the compliments to roll in.
Material: Patent Leather | Sizes Available: US 5.5 – 12.5 | Style: Opera Pump
What To Look For When Searching For The Best Black Dress Shoes
The first consideration when choosing the best black dress shoes for you is the style. You might think that any “dress” shoe will work for any formal occasion, but that isn’t exactly the case. Some dress shoes are dressier than others.
If you want the most formal of all formal wear, a pair of classic Oxfords or Chelsea boots will do you well. Maybe a pair of opera pumps if you’re eccentric. For something a little more casual, a pair of Venetian loafers or chukkas will do the trick. Just don’t show up to a white tie event in a pair of desert boots, and you’ll be fine.
The fit is an essential aspect of a new shoe purchase and finding the best black dress shoes. Obviously, you don’t want to buy something that won’t fit you well. If you have flat or wide feet, you’ll need to factor that into your hunt.
Men with flat and/or wide feet probably know this lesson by now, but ordering shoes online can be a real gamble, so look for something you know will work for you. There are brands like Crown Northampton that make dress shoes for wide feet. You just have to leave a note when placing the order since they’re made-to-order. Pretty high-class stuff, we know.
Depending on the person, comfort is either the most critical aspect or an afterthought. In our opinion, when searching for the best black dress shoes you should at least buy something you can stand around in for a few hours without wanting to tear your feet off. You might find yourself cursing your choice after a long night out if you go style over substance.
I don’t believe in buying uncomfortable shoes. Designers have come a long way since styles like the Oxford came into play; you might as well take advantage of all those years of researching comfy footwear. Even the most brutal shoes to wear 100 years ago can feel like a pair of sneakers today.
Dress shoes have gotten so comfortable that you can wear any type of shoe casually. Personally, this writer would choose something a little more laid back, like sandals, but the right Venetian loafers are just as good for lounging around. They’re called loafers for a reason.
We just wouldn’t recommend wearing your best dress shoes out to the bar unless you have multiple pairs. You want at least one immaculate pair for extra-special occasions.
Unless the dress code specifically calls for it, by no means do dress shoes need to be all black. This guide focuses on black dress shoes, but once you start shopping around, you’ll see there are a fair amount of color options. You won’t find 100 different colors or crazy patterns, but that isn’t what formal wear is about.
Just because it isn’t the same color as your suit doesn’t mean they look bad together. That said, black dress shoes are definitely okay with a navy suit. Excellent, even. The elegance of a black dress shoe elevates a navy suit perfectly. Get some cap-toe or whole, and you’ll be good to go.
Not all black dress shoes will look great with jeans, but some definitely will. You’ll kill in jeans and a nice pair of black leather Chelsea boots. On the other hand, you’d look a bit silly rocking jeans with a pair of brogues. There are probably guys out there who can pull it off (the same guys who can pull off any look), and maybe you’re one of them, but we wouldn’t exactly recommend it.