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,” 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 the comfortable dress shoe brands that will elevate your whole look.