This article is all about our favorite dress shoes that you can buy this year and beyond, no matter what your budget is.
You’d be surprised at how much you can express yourself with a pair of classic dress shoes.
Besides, no matter your job or personal style, dress shoe situations are unavoidable in every grown man’s life. They can also make or break a good suit.
Fortunately it’s 2021 and what were once infractions in formal settings, loafers or suede for example, are now perfectly acceptable as dress shoes if sufficiently smart and well crafted.
The right pair can take you from the boardroom to a formal wedding to box seats at Madison Square Garden. Most importantly, you should feel like yourself in them!
We’ve rounded up the best dress shoe brands, each unique in quality and story, at different price points.
Table of Contents
Let’s Talk Styles
“Dress shoe” is kind of an umbrella term, here’s a breakdown of the different styles of dress shoes…
Oxfords are the quintessential formal dress shoe, defined by a closed lacing system. The flaps above the tongue, where the lace eyelets are located, are sewn under the vamp.
Oxfords are like Sinatra songs: Classic and popular at weddings.
Derby shoes are different from their Oxford cousins only because the facing is sewn over the vamp, for an open lacing system. This makes for a less formal, more versatile dress shoe.
Literally designed for monks as an alternative to sandals, the monk strap shoe features a distinctive strap-and-buckle design.
Single strap shoes offer a clean, elegant silhouette reminiscent of old-school opera pumps. Double straps offer a hint of utilitarian-chic.
Dress boots are fashioned like dress shoes, but the upper goes up to the ankles offering extra support. Dress boots are great for outdoor and weather situations.
My friends and I are an outdoorsy bunch, so whenever we can have weddings and other formal occasions at the top of a mountain or in the middle of the woods, we’ll do it. Dress boots come in handy at such parties.
Chukkas and Chelseas lean casual, but their minimalist look makes them easily styled for smarter situations.
The look of a dress shoe and the ease of a slipper –that’s a winning combination if I ever saw one.
The loafer is the formal brother to the laid-back moccasin, the William to his Harry. It features a heel, a clean upper, and is often made of harder leather than moccasins are.
Brogues and Wingtips
Brogues and wingtips are subcategories of dress shoe styles that can be applied to most of the above designs.
Brogues are defined by decorative perforations.
Wingtips are defined by a W shape design on the toecap.
Both designs have a vintage flare.
Luxury vs Budget
Cement shoes are cheaper than Goodyear welted and Blake stitched shoes, but don’t last as long. Full-grain leather is more durable than rush-processed leather and also comes at a price premium.
It’s true that important fashion brands can, and often do, use the weight of their name to mark up prices, so we’ll explicitly explain the story behind each luxury brand we spotlight.
At the end of the day though, you really do get what you pay for.
Luxury Brands: Over $500
If budget isn’t of concern to you, check out these brands…
Savile Row staple John Lobb is unexaggeratedly the Rolls Royce of men’s dress shoes. This brand has been making footwear for aristocrats since day one.
The sun of the John Lobb universe is its bespoke services, which are also great for gents with smaller feet like me. If you go this route, it may take a year for your Lobbs to arrive, but trust that they will be perfect –and they’ll last forever.
Even the handcrafted ready-to-wear pieces feature telltale signs of topnotch craftsmanship. For one thing, the descriptions are hyper specific about the leather they use.
I don’t exactly know what “forged waxed-leather” is, but I do know that low-quality leather hides behind vague descriptions, and high-quality leather is backed up by objective, superlative-free specifics.
They also offer the widest range of leathers on this list, from calfskin and suede to exotic offerings like lizard and crocodile.
If you feel around the inners of any John Lobb, you’ll notice that their shoe linings are flat and even everywhere including at the seams. This indicates tightly built, well-crafted footwear, and one of the best men’s leather dress shoes in the industry.
Each ready-to-wear design goes through a complex 190-step manufacturing process in Northampton, the cobbler capital of England.
I even love the new limited edition William 75s, which feature distinctive hand-washed colors. This aesthetic dips into contemporary art territory without ever leaving the timeless realm.
Like an Old Master painting or Roman architecture, it doesn’t take an expert eye to understand why John Lobb shoes are so impressive. You’ll admittedly drop a bundle for a pair, but this brand puts their money where your foot is.
There’s always pause among fans when a beloved family company comes under the control of a big luxury brand. Church’s is an English heritage brand that was established in 1873. It was bought by Prada in 1999.
Yes, Prada applied (some would say inflicted) NY Fashion Week trends onto some lines, but they never stopped making the fundamentals. And Church’s factory remains in Northampton.
Church’s hand-made, full-grain shoes remain timeless in style and excellent in quality. I think these are some of the best English shoes out there.
I also fully believe that Church’s and Prada are ideological soulmates when it comes to style. Both use minimalist designs to create a mix of traditional and modern styles.
I’d direct those interested in buying Church’s shoes to their five ICONS, their back-to-basics pieces.
Each classic dress shoe style is represented in its purest, no-frills form. Even their Black Burwood Brogue shoe manages to look restrained.
My favorite among the ICONs is the Amberley R Chelsea in black. It’s a gentleman of a shoe, with a clean Chelsea face and firm leather that isn’t stiff.
If you want a good cigar, go Cuban. A good shell cordovan shoe, go Spanish.
Carmina has been making Goodyear welt constructed shoes on the Spanish island of Mallorca since 1866, and specializes in this highly prized leather.
Shell cordovan is equine leather that was first produced in Cordoba, Spain in the seventh century. Because of its durability and natural resistance to water, it’s often used in high-end shoe making. It’s a rare material priced at about $100 a foot.
Shell cordovan shoes are smooth, and will ripple instead of crease when constantly bent. Shell cordovan requires less maintenance than calfskin leather.
Carmina dress shoes are a happy medium between the exceedingly slick silhouette of Italian shoes and the more muscular shape of English shoes.
A plus for me is that Carmina shoe sizes are great for smaller guys, making most of their models in sizes as small as a US 6 for men.
The Balmoral Dress Boot perfectly represents everything Carmina is all about. It’s as elegant as any dress shoe, but is built sturdily with shell cordovan. The leather is first cut by hand, then the pieces are evened out in bulk to assure a flawless assembly.
For a cleaner outline, there’s also the Black Chelsea Boot, which along with the Balmoral, are two of Carmina’s best-sellers.
Crockett & Jones
Crockett & Jones was founded in 1879 in Northampton. When it comes to shoemaking, Italy is renowned for their leather, but England wins the prize for craftsmanship.
Have you ever watched a James Bond movie and thought, “no way can he run around during these action sequences without tearing up those handsome leather shoes”?
Fiction status aside, 007’s dress shoe of choice is Crockett & Jones.
Sure, no dress shoe is made for chasing a global terrorist on top of a moving train, but Crockett & Jones are known for being well built, timeless, and a craft-focused English heritage brand.
The Highbury Derby Shoe is one of their quintessential shoes. It’s classic, but isn’t as formal as an oxford. As elegant as it is, this derby doesn’t take itself too seriously. What’s more English than that?
Their Sydney Penny Loafer is great for both formal business and smart casual situations because the toe is slightly longer than the average loafer. Moreover, loafers are of English heritage themselves, having first been developed for George VI and his landed gentry.
If you’re somewhat budget-conscious, here are some good picks for you…
In the European-dominated world of luxury dress shoes, Allen Edmonds stands unique as an American heritage brand. They were founded in Wisconsin, provided shoes to the US Army during WWII, and have been sported by several US Presidents.
But Allen Edmonds doesn’t just rely on compelling stories.
They check off all the prerequisites of any comparable luxury European brand: Quality craftsmanship with an in-house process (a 212-step technique), the use of high-quality leathers (shell cordovan, calfskin, and suede), and either Goodyear welt or hand-sewn construction.
What I love most about Allen Edmonds is that they offer unique sizing. Their dress shoes come in a wide range of sizes, widths, and fits, giving options to guys whose feet are too wide, too flat, or as mine are, on the smaller end of the spectrum. Their sizing goes as low as a US 5.
You can also resuscitate old shoes at your local Allen Edmonds store or mail them to the factory using their recrafting service.
The Park Avenue is one of the most popular dress shoes ever. Wearing these timeless oxfords to the office is a lot like wearing a Rolex Submariner in the boardroom -you definitely won’t be the only one sporting them.
That’s a good thing.
These respected staples set the standard for the American dress shoe with their iconic cap-toe silhouette and Horween calfskin leather uppers.
Ace Marks combines the disruptive business practices of an innovative start-up with the craft of a heritage Italian shoemaker.
Launched as a Kickstarter campaign in 2016, Ace Marks has quickly become a renowned and popular direct-to-consumer brand.
Their shoes are handmade in Italy by fourth-generation craftsmen, using hand-selected full-grain leather. They’re also individually hand-dyed and hand-burnished, so each pair is a bit different than the next.
Ace Marks opts for a Blake-stitching over a Goodyear welt construction. This certainly cuts costs, but also makes for a more flexible and immediately comfortable shoe.
I also love that Ace Marks actively participates in conscious capitalism: They’ll issue you a $50 credit for a new pair if you send them your old pair, which is donated to Career Gear, a charity that helps men in need re-enter the workforce.
Ace Marks is all about customer engagement, and the Monkstrap Kurt is one of their most popular and highly rated shoes. They use a proprietary last that reduces common pressure points in the ball and heel, so this Monkstrap is famously comfortable and break-in free.
It also comes in several shades including an unconventional bluish tone called Avio Antique and a yellow-to-brown gradient called Bourbon Nicol. At such reasonable prices, I think there’s room to have fun with color.
After all, handcrafted Italian calfskin shoes like these are triple the price at a heritage brand.
Maybe it was Cole Haan’s stint in the Nike family, but their recent dress shoe lines focus on comfort and flex technology almost as much as athletic shoes or work boots do.
Cole Haan calls the combination of their ergonomic footbed and full-motion outsole their Grand.OS technology. It evenly distributes weight and allows the shoe to freely move with your foot.
Moreover, Cole Haan features a slimmed down construction, which really cuts the fat in the build of their dress shoes for a lightweight, sneaker-like wear.
Newer Cole Haan dress shoes can be pretty hit-or-miss under a certain price point, but you’ll find some quality pieces in the over $300 range.
The Washington Grand Laser Wingtip Oxford is an archetypal dress shoe for the brand because it combines classic looks with quirky details.
It’s a sleek oxford that at first glance looks conservative. However, laser-cut perforations drape the vamp of the shoe then run down the sides and over the top back.
While they’re there for flexibility, breathability, and moisture control, they also give the shoe an original, and modern look unique from, but not fully rebelling against, traditional dress shoes.
Finally, the precision engineering, cushioned memory foam, and flex welt have many reviewers claiming it’s an athletic shoe disguised as a dress shoe.
If your budget allows spending between $100 and $250, here are some options to choose from…
In the same vein as Tom’s or Warby Parker, Beckett Simonon is focused on sourcing responsibly, supporting ethical manufacturing, and acting sustainably.
Beckett Simonon was founded in 2012 in Colombia, and is also a direct-to-consumer brand offering footwear at shockingly affordable price points, especially given the quality of their dress shoes.
Their shoes are made in small-batch runs. Every month, Beckett Simonon releases several styles on their website. They’ll then produce each style in lots based on customer orders, leaving no unused inventory.
This efficiency gives them the bandwidth to source high-quality full-grain leather and use ethical labor without charging you the price of courtside game tickets.
This also means you’ll wait somewhere between six to eight weeks for your shoes to arrive when you’ve ordered them online, but you’ll receive updates about where they are in the production process during the wait.
I’m a big fan of Beckett Simonon’s Durants. With its oxford-gone-brogue style, the Durant is beautifully unusual. The heavy Adelaide broguing makes it a statement shoe, and the full-grain Argentinean calfskin makes it an essential Beckett Simonon.
The Royce Longwings are a similar style, but with even more perforation and wingtips to boot. At such a low price point, why not go the statement route?
These specific Beckett Simonons do run thin though, so they aren’t great for the wide footed fellow.
Johnston & Murphy
I consider Johnston & Murphy one of the great mid-range brands.
They aren’t a trendy brand. Abe Lincoln being one of their patrons, Johnston & Murphy focuses on classic American styles. Even they’re contemporary lines are mainly remakes of the tried-and-trues. In fact, one of their most highly rated shoes is a saddle shoe.
Many of their lines are wider and more comfortable than conventionally thinner dress shoes like the Beckett Simonon Durants. They also tend to run big, so I recommend sizing down a half a size. Several Johnston & Murphy lines offer sizes as low as a US 6, but this isn’t the case with all models.
I always say a mid-level shoe that incorporates a few high-quality features is a better buy than an expensive high-fashion piece that’s marked up because of brand recognition.
Their Bryson Tassel Slip-on has a cool vintage dad flare, but isn’t out of place today, and their Conard Cap Toe, which is handmade with Italian leather, is one of the best affordable men’s dress shoes.
Wolf & Shepherd
Wolf & Shepherd, like Cole Haan, focuses on athletic-level comfort for historically uncomfortable dress shoes.
Unlike Cole Haan, this brand didn’t evolve into that focus, but was founded on it. In 2014, student athlete and performance shoe and technology designer, Justin Schneider, founded Wolf & Shepherd after years of experimentation.
Because of its tech-focused, start-up background, Wolf & Shepherd shoes tend to be more relaxed than Cole Haan’s dress shoes. They’re most known for their hybrids, which combine a full-grain Italian leather upper with an agile rubber sole.
Wolf & Shepherd shoes are designed with running shoe technology, using a proprietary blend of memory foam and a carbon-fiber stability arch.
If you work in a start-up culture environment, I say go for the hybrid shoes. I’ve seen tech professionals sporting the middle-ground style of the Crossover Longwing in and out of the workplace.
They do offer more traditional looking dress shoes that also incorporate comfort technology. The Closer Cap Toe is a great example, which also comes in sizes as small as a US 6 and as large as a 15.
If you’re creative enough, or have treasure-hunting tendencies, you may be able to find a great dress shoe under $100.
Even some of the previously mentioned brands sometimes offer dress shoes in this price range. Cole Haan, for example, often has online sales on their website.
Florsheim offers a few popular budget models.
Because they’re in completely different ranks, people forget that Florsheim grew up with Allen Edmonds. They’re both heritage brands born in the Midwest, after all.
At one point, as we can see today, Florsheim shifted their focus towards efficiency.
The contemporary world of dress shoes is an exciting one.
Your grandfather would be shocked to know that sneaker-dress shoe hybrids are allowed anywhere near the office.
However, whether your leaning into traditionalism or quirkiness, a proper dress shoe is rooted in the classics. Each of these brands understands that, and because each man has a unique lifestyle and story, it’s a win there’s such a wide spectrum of offerings for the staple dress shoe today.