In days of yore, the best dress shoes for men might’ve matched the bronze rim of your monocle, the wood of your walking cane, or the hem of your bowler hat. In these, less formal days of dressing up, the modern dress shoe still retains a surprising amount of versatility as casual and formal dress codes further intercede.
So you’ve got your bespoke suit and collected an array of complementing accessories. Don’t let any old shoes take away from your impeccable style. Good tailoring requires formal shoes with real panache to help ground all the hard work you’ve put in. The formal dress shoe is by no means an anachronism. With the world opening once again—weddings, friends, dinners, events, life—there’ll be more opportunities than ever to slip on your leather-clad friends.
Remember, you are not a prisoner of the dress shoe’s formality. Nor do you have to wait for the perfect event to wear them (except for the John Lobb shoes, you’ll see). Feel free to mix them into more casual outfits: brogues, chinos, and an oversized white shirt? Loafers with casual light wash jeans? Derbies with cords? But whatever you do, don’t dare try to taint the oxford shoe with a smart-casual slant. By gum, we at Fashion Beans will not be happy.
With so many dress shoe variations, this is by no means an easy process. Oh no. Strap in. We’re here to guide you through the sub-categories, nuances, and intrigue of it all. If knowledge is power, then this in-depth fashion guide on the best dress shoes for men is pure consumer-purchasing-power. Read forth.
Formalwear has been de rigueur in menswear for centuries, so many styles we know and love have solidified into rigid forms. This is why it’s so easy to spot genuine novelty and ingenuity in design—it stands out like a beacon. It’s subtle but the asymmetrical double-monk breast sweeps the shoe’s shape with admirable finesse.
These Ralph Lauren double monk shoes are Benchmade in England, the heartland of the cobblers (shoemakers). That means even though the template shape is plastic molded, the shoe is hand-worked by a “bench” of artisans. Fancy.
Material: Leather | Sizes Available (US): 7-10.5, 11.5, 13 | Colors available: Black, Brown | Fit: Regular
Grenson is one of the best-known brands from Northamptonshire, England. This classic Canterbury silhouette proves their heritage is still intact. The intricate brogue detailing and the squared toe bring panache to its formality. Though a slim-fit black suit might seem the obvious styling choice, try this modern tailoring from Officine Générale in a lovely grey tone. The shoes are smart yet so full of personality that they’ll give this more relaxed tailoring the sharpness it needs to balance it out.
Material: Leather | Sizes Available (US): 7-11, 12-13 | Colors available: Black | Fit: F: Standard Fit
How do I know these shoes are the most comfortable dress shoes money can buy? I own a pair, and I cannot stress enough the almost baffling softness of that rubber sole. It’s like walking on very tacky sponges. Or rubber clouds. It’s the inverse experience of wearing some very painful, bloody, and gruesome dress shoes in the past.
The magical black rubber soles then blend up into the dark brown leather upper, making for an aesthetically pleasing overlap. I wore these trendy dress shoes with thick black wale cords and an oversized grey knit with blue details. The whole ensemble looked amazing (if I do say so myself), and it was largely thanks to the shoes.
P.S. They’re not lying about the sizes running large. Go for a smaller than usual size.
Material: Cow Leather | Sizes Available (US): 8-12 | Colors available: Black, Dark Brown | Fit: Runs Slightly Large
Oh, the Verve. The bittersweet symphony of these shoes. A stylish white leather penny loafer that somehow avoids garishness. How? It’s the vintage shape, the über luxury interlocking “YSL” logo in gold lettering, and the low-block heels. These shoes are so stylish they’ll make Richard Ashcroft want to write a song about them.
When styling white shoes, think about the attention they demand. Normally, we’d say try to dress plainly elsewhere and let the shoes be the centerpiece, but with a pair of white leather shoes, you have to match its loudness.
Try straight-legged white jeans, a flamboyant shirt, and a suede jacket. If you’re going to wear white shoes, you have to go all in. And make sure you’re somewhere exotic at dusk with a cocktail in your hand, and there’s some upbeat Mexicana music playing in the background. If possible.
Material: Leather | Sizes Available (US): 7-12 | Colors available: White | Fit: Standard
It’s said that Louboutin saw an employee putting on red nail polish, and he was struck by an idea. He snatched the nail polish out of their hands (slight embellishment) and began furiously painting the sole of a shoe red. That is how the iconic Louboutin red-soled shoe was born.
Over the years, the Louboutin dress shoe has been graced by ‘red carpet’ celebrities such as… [insert every celebrity to attend a red-carpet event]. If it’s good enough for them, it’s good enough for us.
Styling the red-soled shoe? Make sure you have the requisite suave to back it up. We suggest saving these for a black-tie event and wearing them with a satin side-striped tuxedo to match the shoe’s bougie red-carpet feel.
Material: Leather | Sizes Available (US): 6-13 | Colors available: Black | Fit: Standard
The aesthetic simplicity of these Cheaney oxfords sort of hides their practical depth. The double-leather sole attaches to the hi-shine leather upper via a traditional Goodyear welt. These shoes are stylish, formal, and very adept at combining with traditional tailoring.
Founded in 1886, Cheaney is another famous cobbler from Northamptonshire. Skilled workers use traditional methods to make shoes of the highest quality. But if anything does happen to the shoes in the meantime (such are the untamable vicissitudes of life), then Cheaney offers three highly comprehensive aftercare plans. Standard, imperial, and heel.
The traditional methods of making high-quality shoemaking and comprehensive aftercare are of huge importance in modern-day sustainability parlance, making these derbies both old-school and progressive. And they said it wasn’t possible…
Material: Leather | Sizes Available (US): 7-13 | Colors available: Black | Fit: G: Wide
Personally, I’m a no-toe-cap-kinda-guy, but with these elegant Bruno Marc dress shoes, you can take your pick. Plus, you can choose light brown, dark brown, and black. Although there is a strong case for thinking this isn’t a choice at all. It’s almost imperative to have all three in your wardrobe.
A breadth of shades of leather provides maximum versatility and scope for effective styling. Simple. Chic. Variable. These Bruno Marcs are a styling savior sent from styling heaven. The 100% vegan leather is a nice bonus too.
Material: Leather | Sizes Available (US): 6.5-15 | Colors available: 6 Options | Fit: regular
While a pebble grain leather tends to knock a dress shoe down a few rungs on the formality ladder, it does make for a lovely tactile experience. Take your pick: sensuousness or formality. That’s always the trade-off, isn’t it? With this pair of Thom Browne longwing brogues, the supreme quality and simplicity of styling mean you also retain formality. Who said you couldn’t have it all?
The red, white, and blue heel pull motif is a practical way to put shoes on and a stylish departure from the norm. These shoes are American chic with English shoemaker heritage, making them a very special pair of shoes.
Material: Leather | Sizes Available (US): 6-12 | Colors available: Black | Fit: Regular
Until the 16th Century, leather shoes were handmade by small groups of artisans in Almansa until larger factories arrived. Being close to Madrid with good transport connections to the rest of the country allowed it to become the capital of shoemaking in Spain. Comovita is now tapping into this artisanal and manufacturing heritage.
This pair of Oxfords are handmade, tallying up over 200 steps in the process. Its soft, supple suede and rubber soles will make light work of regular use too. Wear with beige trousers by Racing Green and a relaxed white shirt by Arket for a failsafe smart-casual office outfit.
Material: Suede | Sizes Available (US): 4.5-14 | Colors available: Brown | Fit: Regular
You only need to look at these John Lobb oxford shoes to know they’re cut from the fabric of an alternate universe. The stitched lines, curving outsole, and easy double-stitching at the heel of the ankle suggest artisanal perfection. It looks more like a Sunseeker superyacht than a pair of shoes.
They hail from the brand’s Northamptonshire factory, so it shouldn’t be a surprise they’re constructed of excellent refined black leather. To retain their prestige and do them right, only wear them with the finest of tailoring at the finest of occasions. Save them for when it matters. These are a work of art.
Material: Leather | Sizes Available (US): 6-13 | Colors available: Black | Fit: Medium Width
The royal warranted family brand Tricker’s was set up in 1829 by Joseph Tricker, and they know how to define the Oxford shoe by the “closed throat” construction. The two leather sides lace up and meet perfectly in the middle, imbuing the design with a sense of symmetry and formality.
Consider the formal essence of an Oxford shoe captured. The brand has taken these well-worn tropes and enhanced them with a modern square-toe, brogue detailing, and espresso tint leather. We suggest styling with a brown, beige, or off-white suit. Ideally, brown in the winter and linen-beige in the summer.
Material: Leather | Sizes Available (US): 8-13 | Colors available: Espresso Brown, Black, Burnished | Fit: Standard Width, or UK–F, or USA–D, or M (medium) or R (regular)
George Cleverly started with a high-class pair of Derby shoes, but they went even further. They put the heavy-tread winter tires on and converted it to an ATV. If the Vibram lugs weren’t enough, they’re also storm-welted. So now you get a 360-degree welt with much better protection and waterproofing.
If you plan on getting to your next wedding by running through miles upon miles of muddy bogs, definitely consider these Vibram-soled monsters. If not, the current trend is very much leaning into chunkier soles, so there’s always that to fall back on.
Material: Leather | Sizes Available (US): 8-11, 12 | Colors available: Black | Fit: Normal
Sometimes, all you need is a selection of chocolate, cognac, and tan suedes to match your tailoring. Fairfax & Favour is a relative newcomer to the market, but the brand has established a niche through its English equestrian and outdoorsy roots.
This pair of suede dress shoes feature immaculate “brogueing,” which isn’t some sort of lovely bro-hugging but patterned leather perforations. A brogue shoe is also known as a wingtip because the patterns emulate the linear shape of wings from the toe to the heel. These shoes have the ability to match smart-casual and formal styles alike. They’re a versatile choice.
Material: Suede | Sizes Available (US): 7-15 | Colors available: Cognac, Chocolate, Tan | Fit: Wide
The 3oz full-grain chocolate leather and the thin black sole make for a suave pair of loafers. The leather itself is finding it hard to give up its Italian national identity. It resonates with the “Sprezzaturra” (nonchalant style) spirit and looks as though it has a deep love of La Passegiata (wandering around at the end of the day chatting).
And yet, these shoes are the product of the high ethical standards of Portuguese factories. Some might say the wonders of the global economy, whereas
Material: Leather | Sizes Available (US): 6-15 | Colors available: Chocolate, Black | Fit: Regular
Whack the classic
Material: Leather | Sizes Available (US): 6-10.5, 11.5-13 | Colors available: Black | Fit: Standard
We arrive at the imperious grandeur of the monk shoe: a personal favorite. They have gained contemporary favor due to their ability to match with casual, smart-casual, and tailoring alike. But contemporary, they are not. Monks between 1000-1350AD wore a sandal-like pump with a strap that was secure and tough enough for outdoor work. We guess the shoe was just called “strap” back then, though.
Loake is yet another example of a family-owned Northamptonshire cobbler “granted a Royal Warrant by Appointment of HM The Queen for the manufacture of Men’s Footwear” in 2007. While this particular shoe dates back to the 1880s, like the brand itself and monk-strap shoes at large, it’s showing no signs of aging.
Material: Leather | Sizes Available (US): 6-13 | Colors available: Black, Dark Brown | Fit: F: Regular
A black patent shoe is a thing of elegance and simplicity—a style that shouldn’t change. Renowned British shoemaker Crockett & Jones has exercised creative restraint, utilizing a lightweight sole and welt. The only slight nuance is in the exaggerated stitching through the upper. This gives it a touch of its own personality.
If formality is about dexterity, precision, and charm, then these Crockett & Jones shoes have all three in plenty. Good, good, good.
Material: Patent Leather | Sizes Available (US): 6-13 | Colors available: Black | Fit: Regular (E–UK size)
These Myrqvist shoes are quotidian dress shoes. Not in the sense that they’re dull or drab. But in the sense that they are so wearable. You can thank the grained brown leather combined with just a singular monk strap. You’ll be swapping out your Phylon midsole sneakers for these sleek beauties in no time.
This is a shoe that can travel the spectrum of formality, from a smart-casual denim pairing to a brown/navy blue three-piece. Just make sure you keep these shoes polished and in good condition.
Material: Country Calf Leather | Sizes Available (US): 6.5-12.5 | Colors available: Dark Brown | Fit: Regular
What To Look For When Searching For The Best Dress Shoes For Men
Type (loafers, oxfords etc.)
Loafers: Shoes without any fastening system. They’re slip-on.
Oxfords: “Closed lacing” where the two eyelet tabs form a neat closure. This is the most formal style.
Derbies: The eyelet tabs don’t form a neat closure hence why they are known as “open lacing.”
Brogues: Patterning via leather perforations. It’s often called wingtip because it stretches from the toe to the heel like a wing.
Monk-strap: A leather flap secured by small buckles at one side holds the foot in place.
Mass-produced or even Benchmade dress shoes have come through the tradition of bespoke shoemaking. This means there are variations in shoe fit, generally, through the width. You’ll notice manufacturers referring to “lasts,” meaning the tooling or the template shape for that shoe, and each last is individual.
To make things less confusing, there are industry-wide standards. In the UK, a standard size fit is known as an “F.” In America, it’s “D.” And elsewhere, it’s “R” for regular or “M” for medium. A wider fit is “G” (UK), “E” (USA), and elsewhere it’s “wide.” Finally, extra-wide is “H” fitting (UK) and termed “extra-wide” elsewhere.
If they aren’t bespoke to your foot, a good pair of leather shoes will take a while to break in. This is natural since the leather and the stitching need to loosen up. For a pair of shoes to be worth their money, they need to be comfortable. That is paramount. If in doubt, have your foot measured or measure your own foot. Most manufacturers provide specific shoe size information so you can avoid disappointment.
Dress shoes are traditionally formal, smart, and worn with tailoring. This makes the category a fairly broad one, but generally, they’re made from leather and have a high degree of formality.
As the general trend tends to move to casual, it’s no surprise that the more casual dress shoes are the most popular. A good pair of loafers can be an extremely desirable, trendy, and versatile purchase. Derbies fall under the same category, as do single-monk straps. In the previous few years, large chunky soles have become increasingly available to add a fashionable edge to an otherwise standard dress shoe.
There are a few things you’ll have to know. First, your budget. This will decide if you go with a bespoke pair, a Benchmade pair, or mass-produced. Second, know your size. Either measure your foot yourself to buy online or get measured and try on shoes in-store.
When purchasing dress shoes, consider the tailoring and smart-casual clothing you already have, also any smart shoes you already have. What are the gaps in your styling? How could the next pair fill that space? Diversity gives you better choices. If none of this makes any sense… begin with our basic rules for menswear styling.