27 Best Dress Shoes For Men

These are the best dress shoes for men whether you need a pair for business or formal wear...

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Even today, you can still tell a gentleman by his shoes. Whether deliberate or not, one’s choice in men’s 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 for men 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 for men to buy right now. And, with the help of two knowledgeable luxury footwear experts, you’re about to discover the dos and don’ts of men’s dress shoes. Hint: it’s all about quality and being prepared to pay for it.

Which Dress Shoe Style Is For You?

Before we get into what to expect from a pair of shoes depending on how much you’re able to spend, it’s important to get the various styles out the way first, as it’s not necessarily as simple as just going out and getting a pair for work or a formal event. Each style has its own uses and connotations.

Oxford Shoes

The most formal and elegant of the dress shoe styles, the Oxford distinguishes itself by a closed lace system. The eyelets for the shoelaces are generally located on the quarters – the 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).

Oxford shoes are ones you would certainly want to be seen wearing in the boardroom at work. Their formal nature imparted by their closed lacing system will let others know you know how to dress and just how much of an impact a good pair of shoes can make. If you do invest in Oxford shoes, you’ll want to spend as much as possible to get a long-lasting reliable pair.

Derby Shoes

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. Derby shoes can be worn to the office no problem, although if you’re higher up in the pecking order, then we’d recommend you steer more towards the Oxford.

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. To stand out from the crowd at a wedding, for example, the monk strap shoe is the way to go.

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.”

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.

Well-Made Is 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 for men 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,” says 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 comfortable dress shoe brands if you’re more concerned about comfort than style.

Best Dress Shoes For Men FAQs

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If you still want help on choosing a pair of men’s dress shoes, we’ve got you covered. These are the best dress shoes for men to buy right now.

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