20 Dress Shoes Every Man Should Own

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1 of 20|Santoni|BUY - LINK
2 of 20|Paul Smith|BUY - LINK
3 of 20|Gucci|BUY - LINK
4 of 20|Church's|BUY - LINK
5 of 20|Carmina|BUY - LINK
6 of 20|Edward Green|BUY - LINK
7 of 20|Salvatore Ferragamo|BUY - LINK
8 of 20|Dolce & Gabbana|BUY - LINK
9 of 20|Alden|BUY - LINK
10 of 20|Allen Edmonds|BUY - LINK
11 of 20|Zonky Boot|BUY - LINK
12 of 20|John Lobb|BUY - LINK
13 of 20|Loake|BUY - LINK
14 of 20|Saint Crispin|BUY - LINK
15 of 20|Grenson|BUY - LINK
16 of 20|Crockett & Jones|BUY - LINK
17 of 20|Tom Ford|BUY - LINK
18 of 20|Berluti|BUY - LINK
19 of 20|Hugo Boss|BUY - LINK
20 of 20|George Cleverley|BUY - LINK

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 2016. 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!”

Keys Colours & Styles

When assembling your dress shoe arsenal, make sure you cover all your bases pertaining to classic colours and styles. “Look to black, brown and oxblood across derbies, oxfords, double monks and brogues and a collection of loafers,” says Poulakis.

The Oxford


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).

“The black cap toe Oxford is an essential, unavoidable shoe,” says Schaerf. “This is a shoe for weddings, funerals, black tie events and conservative jobs like banking or law.”

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.

“The brown Derby is a great all-rounder,” says Schaerf. “This is dressy enough for almost any occasion, but also goes nicely with chinos or a sports coat.”

Double Monk


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.

“The monk is obviously a favourite of mine and there is really nothing else like it,” says Schaerf. “It has the potential to be as dressy as an oxford or as casual as a loafer depending on the style. But the buckle brings a touch of flair and a point of difference.”

The Loafer

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.”

The loafer’s formality depends on how and what you wear with them — stepping up with a separates combination that’s ideal for business casual Fridays or chinos and polo shirt for a smart casual weekend. “Overall, the best thing about loafers is that they can look dressy and relaxed at the same time.”

The Brogue


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. “They vary, from the dressy punch-cap brogue known to the London banker, to the semi brogue, which features broguing at the toe and heel, all the way to the full or wingtip brogue, which is really a country shoe — although it does have some refined examples that can look good with a suit,” says Schaerf.

The Dress Boot


Rugged style, a well made dress boot repays you in spades, says Schaerf. “You can wear with both casual and relatively dressy outfits. Most importantly, though, it will be built like a tank. And, since boots are usually the footwear of choice for foul weather, having one that will deal with the elements is ideal.”

Final Word


Keep your current wardrobe in mind while shopping for your next pair. Step into footwear that complements, not contrasts, with the tailoring you already own. “Basically, it’s important to build a wardrobe of shoes to match your suits and trousers,” concludes Poulakis.

Investing in lasting styles and colours is important, shopping around for quality, and a top price. “Overall, buy the best shoes you can afford to buy and do everything you can to look after them. Keep this in mind and you will slowly build a collection that you can keep for the rest of your life,” says Schaerf.

  • Amir Delane

    New Rock’s Newman 2802 is the only shoe for formal dressing for me.

  • Gus_Cox

    Nice article on shoes, but I could do without the pictures of hipsters wearing good shoes on their bare feet. It’s disgusting, and it’s bad for the shoes. It’s about as stylish as armpit stains.

  • http://ypx.jerseydreams.nut.cc/ mcarmona1

    I disagree.

  • http://n1BEOX5AuJfTwu1wC.uk n1BEOX5Au

    885026 19021Enjoyed reading this, really excellent stuff, appreciate it. 83183

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