The Playbook For The Modern Man

32 Best Men’s Dress Shoes To Own Your Next Business Or Formal Adventure

Oxfords not brogues…

Dress Shoes Featured Photo

Even today, you can still tell a gentleman by his shoes. Whether deliberate or not, one’s choice in leather dress shoes – Oxford, Derby, monk or brogue – can still point the way to a man’s character: is he stylish or not?

Because quality and aesthetically on-point dress shoes can cover a multitude of fashion sins. And done cheaply, pleather knock-offs with a square toe cap can undo hundreds of dollars invested in a made-to-measure suit. Seeing the importance of getting it right?

Stepping you in the right direction, we’ve uncovered the best dress shoes and brands for men in 2019. And, with the help of two knowledgable luxury footwear experts, you’re about to discover the do’s and don’ts of men’s dress shoes. Hint: it’s all about quality and being prepared to pay for it.

Well-Made’s Worth It

While most luxury shoes are $400-plus, their quality, craftsmanship and longevity far outweigh the hefty price-tag. “Like with everything in fashion, investing in lasting, timeless footwear is the key. A well made pair of shoes can last a lifetime if not generations,” says Ross Poulakis, founder of luxury retailer, Harrolds.

And, whether you go bespoke or not, luxury dress shoes are made for you. “High quality shoes, if well fitted, will mould to your foot over time and provide support and comfort as they wear in,” says Nick Schaerf, co-founder of luxury men’s shoe store, Double Monk.

Cheap Vs. Luxury

“Goodyear welting, hand painting, hand stitching and premium leathers are common techniques that speak of the artisanship that goes into the construction of luxury footwear,” say Poulakis.

While exotic crocodile and ostrich skin shoes are on offer, the most common leather is cow, full-grain calf leather and “sometimes Cordovan, which is from a horse,” says Schaerf. “Full-grain leather can be conditioned and treated to remain soft and supple for decades.”

The way the leather is stitched and welted is also very important. “Most high-end Italian shoes are Blake stitched, built for loafing around in piazzas rather than commuting or wearing several days a week for years on end.”

Still in Europe, English shoemakers can’t be beaten for sturdiness, says Schaerf.

“The English bench-made shoe has its origins in military boot making, so durability has always been paramount, with refinement coming over many decades,” he adds. The cornerstone component? A Goodyear welted sole.

“The Goodyear-welted construction allows the shoes to be re-soled over and over again, so in theory the shoes can last indefinitely. Some of our customers have had their shoes for forty or fifty years!”

And once you’ve got your shoe game sorted, check out the coolest sock brands for men to rock today and the comfortable dress shoe brands that will elevate your whole look.

The Best Men's Oxfords

The Oxfords

The most formal and elegant of the shoe types, the Oxford distinguishes itself by an closed lace system. The eyelets for the shoe laces are generally located on the quarters — that part of the shoe uppers that wrap around the heel and meet the vamp (the shoe uppers that cover the toes and instep in the middle of the foot).

Scarosso Cap Toe Black Oxford $245
Belsire Handmade Cap Toe Oxford $245
Allan Edmonds Park Avenue Cap-toe Oxford $395
Carmina Black Cap Toe Oxford $450
Grenson Gresham Cap-Toe Leather Oxford Shoes
Grenson Gresham Cap-Toe Leather Oxford Shoes $635
Crockett and Jones Hallam Cap-Toe Shoe in Black
Crockett and Jones Hallam Cap-Toe Shoe in Black $895
Kingsman George Cleverley Merlin Whole Cut Leather Oxford Shoes
Kingsman + George Cleverley Merlin Whole Cut Leather Oxford Shoes $1,000
Paul Smith Men's Dark Brown Suede 'Carlisle' Oxford Shoes
Paul Smith Men’s Dark Brown Suede ‘Carlisle’ Oxford Shoes $875
Bally Scanio Men's Leather Oxford Lace-up Shoe in Black
Bally Scanio Men’s Leather Oxford Lace-up Shoe in Black $1,350
Edward Green Chelsea Cap-Toe Burnished Leather Oxford Shoes
Edward Green Chelsea Cap-Toe Burnished Leather Oxford Shoes $1,767
George Cleverley Nakagawa Cap-Toe Leather Oxford Shoes
George Cleverley Nakagawa Cap-Toe Leather Oxford Shoes $2,018

The Best Men's Derby

The Derby

A less formal leather lace up, the Derby is characterised by quarters with shoelace eyelets that are sewn on top of the vamp. This construction is known as open lacing, compared to the closed version of the Oxford.

Lloyd Pointed Toe Derby Shoes
Lloyd Pointed Toe Derby Shoes $210
J.Crew Oar Stripe Shortwing Derbys
J.Crew Oar Stripe Shortwing Derbys $533
Tod's Suede Derby Shoes
Tod’s Suede Derby Shoes $554
Tiger of Sweden Black Sennit P Derbys
Tiger of Sweden Black Sennit P Derbys $562
Church's Oslo Polished Leather Derby Shoes
Church’s Oslo Polished Leather Derby Shoes $663
Crockett and Jones Highbury Plain-Toe Shoe in Black Calf
Crockett and Jones Highbury Plain-Toe Shoe in Black Calf $908
Berluti Leather Derby Shoes
Berluti Leather Derby Shoes $2,605

The Best Men's Double Monks

The Double Monk Strap

For traditional purists, the double monk is something unique. Fastened, not with laces but two leather straps with a metal buckle closure, it’s a die-hard favourite among contemporary gents with nostalgic tastes.

Doucals Suede Monk Shoes
Doucal’s Suede Monk Shoes $338
Reiss Lansen Leather Double Monk Strap Shoes
Reiss Lansen Leather Double Monk Strap Shoes $510
George Cleverley Thomas Cap-Toe Leather Monk Strap Shoes
George Cleverley Thomas Cap-Toe Leather Monk Strap Shoes $764
Crockett and Jones Harrogate Double Monkstrap Shoe in Dark Brown
Crockett and Jones Harrogate Double Monkstrap Shoe in Dark Brown $1,000

The Best Men's Loafer

The Loafers

From the tassel to penny loafer, the laceless leather dress shoe is a more relaxed, versatile option. “Some guys hate loafers. But for those who don’t, loafers are the perfect shoe for when you can’t think of what to wear,” says Schaerf. “The no-lace factor appeals to our lazy side.”

Berwick Shoes Classic Loafers
Berwick Shoes Classic Loafers $200
Grenson Maxwell Loafer Espresso Velvet Suede
Grenson Maxwell Loafer Espresso Velvet Suede $275
Allen Edmonds Salerno Penny Loafer
Allen Edmonds Salerno Penny Loafer $485
Salvatore Ferragamo Gancini Loafers
Salvatore Ferragamo Gancini Loafers $515
Allen Edmonds Grayson Dress Loafer
Allen Edmonds Grayson Dress Loafer $555
Tod's Nubuck Penny Loafers
Tod’s Nubuck Penny Loafers $556
Paul Smith Men's Black Leather Larry Tasseled Loafers
Paul Smith Men’s Black Leather Larry Tasseled Loafers $660
John Lobb Lopez Suede Penny Loafers
John Lobb Lopez Suede Penny Loafers $2,687

The Brogue

The Brogues

Classically English, the brogue – with its perforated leather patina – is a great smart casual shoe and is perfect with a tweed blazer or waxed cotton jacket and jeans or chinos.

Allen Edmonds Boulevard Cap-Toe Dress Shoe
Allen Edmonds Boulevard Cap-Toe Dress Shoe $350
Grenson Stanley Dainite Sole Brogue
Grenson Stanley Dainite Sole Brogue $379
Tricker's Bourton Derby Brogue
Tricker’s Bourton Derby Brogue $625
Church's Toronto Cap-Toe Leather Oxford Brogues
Church’s Toronto Cap-Toe Leather Oxford Brogues $641
George Cleverly Reuben Full Grain Leather Wingtip Brogues
George Cleverly Reuben Full Grain Leather Wingtip Brogues $762
Edward Green Inverness Leather Wingtip Brogues
Edward Green Inverness Leather Wingtip Brogues $1,767

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