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 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 to buy right now. And, with the help of two knowledgable 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.
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.
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.
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.
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.”
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 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!”
Best Dress Shoes For Men FAQ
How do I lace my dress shoes?
There are several variations you can use to tie your dress shoe, with the criss-cross and straight-bar methods being the most common and mos popular.
However, you shouldn't cross the laces if you have a pair of Oxfords because it will cause bumps under the vamp. Only use the cross lacing method on Derbies and Bluchers.
What colour dress shoes should I wear with a navy suit?
Navy suits can be paired with a few colours for dress shoes. Black and brown/cognac coloured dress shoes work the best, though.
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If loafers are what you're after, then you've come to the right place, with nearly 100 pairs to choose from. You will find a few pairs of Oxfords and other lace ups, but for slip supremacy, there's nowhere better to go.
Why stop there? the design team asked. Why not outfit guys from head to toe in Hugo Boss? That's exactly what you can do with the brand's considered footwear collection. Derbies and Oxfords dominate the lineup, with both styles being offered in various shades of brown and black, and for those who want to inject some alternative style, you'll find chunky sole variants too.
They only have one shoe to offer, ‘The Original’, which is a stylish dress shoe available in four timeless colours. But this shoe is secretly a serious game-changer when it comes to men’s dress shoes. The soles of The Original are crafted with new, proprietary materials created by Amberjack that deliver comfort all day long! The shoes also feature heat-activated arch support made with foam (that’s more durable than memory foam) that when heated by your body warmth will mould to your foot for custom arch support.
Not to mention a dual-density outsole with high-performance athletic technology in the front for flexibility and strong hiking boot material in the back for support. Oh, and the sustainably sourced Italian suede used for the upper is water repellent, meaning you can wear these dress shoes in rain or shine, and the suede will stay protected and fresh. Seriously, these will be the most comfortable yet stylish dress shoes you’ll ever have.
Reiss' dress shoe range isn't the largest ever, and you won't find any Oxfords, but instead you'll be able to choose from Derbies, Loafers and Monk Straps, all of which use high-quality leather and are made in Italy.
Charles Tyrwhitt also has a generous selection of dress shoes to match, ticking off Oxford, Derby, Monk Strap, Brogue and Loafer styles. Goodyear Welts feature across much of the range, as do both leather and suede
Ted's dress shoe range encompasses Loafers, Derbies, Brogues, Oxfords and various styles of boot, many of which introduce subtle pops of colour, lending them to being versatile enough to be worn for semi-formal and formal events.
Johnston & Murphy
While J&M does blur the lines between formal and casual for its main shoe collection, the company also has a range of dress classics, which comprises several pairs of Oxfords in various colours. The company's XC4 range (which is performance focused) also encomapsses pairs that can be worn in more formal situations.
The drs shoe range is made up of a fair number of loafers which lend themselves to being worn with more semi-formal and business-casual outfits too, alongside Derbies, that can be resoled in the future thanks to a Goodyear Welt and well-fitting thanks to a generous selection of sizes.
There are hundreds of pairs of shoes within ALDO's dress collection (including a large number of loafers), and for traditionalists, there are several pairs of Oxfords and Derbies in a variety of colours and fits.
Doucal's shoe range encompasses all the major styles and colours, and offers select pairs with varying heights of heel to help you achieve the perfect look for you.
All dress shoe styles are catered for in Myrqvist's collections, with both leather and suede used across the ranges. In some instances, you can even customise the sole to be either full leather or half-leather and half-rubber.
You can still be confident of a well-made pair of Oxfords or Derbies, however, as Lloyd is keen to uphold its years-long reputation for being a manufacturer of choice for businessmen the world over.
Crockett and Jones
Crockett & Jones has been the official boot supplier to the British Army during WWI and has been on the receiving end of a few awards direct from the British Monarchy. With a number of boutiques in high-end fashion destinations including London and Paris, C&J represents the absolute pinnacle in quality.,
The company remains in northern England today and produces around 350 pairs of shoes a week. It might not sound like many, but considering they're all handcrafted proves just how much time goes into creating each individual pair. Edward Green also prides itself on its lasts (the 'mould' for want of a better word, that each pair is based on) as they offer unique profiles and supreme comfort. You'll find pairs encompassing the Oxford style, double and single monk strap and even whole-cut shoes, which are made from a single piece of leather.
Today the company continues to exude luxury, with all pairs being put together by hand using soft and supple leathers, Goodyear welts and Lasts that have quite literally stood the test of time. If you have a pair of Church's in your dress shoe collection then you can confidently claim to be at the top of your footwear game.
John Lobb not only has pairs of shoes covering Oxford, monk strap, loafer and derby, but also offers a bespoke service, allowing to order a pair of shoes that cut to fit your exact dimensions. You can't get more comfortable than that.
TAFT has a huge range of extremely well crafted dress shoes, all made with premium leather, in a variety of unique styles that’ll make you stand out in a crowd.