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.
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.
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.
“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.
Amberjack
A relatively new brand, launched in November 2020, is Amberjack. The Amberjack team has had years of experience though, working with some of the biggest heavyweights in the men’s footwear industry such as Cole Haan, Allen Edmonds, and Adidas.
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.
GH Bass
Founded way back in 1876, GH Bass has remained committed to producing a huge range of shoes that encompass both classic designs and styles along with good-looking pairs that are a little bit more 'out there'. The best thing about GH Bass, however, is how well their shoes are priced.
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.
Hugo Boss
Think formal attire and you can't really skip past Hugo Boss. The high-end German menswear brand is somewhat synonymous with formal dress, with its suits being among some of the best in the business.
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.
Scarosso
Scarosso is an Italian manufacturer of leather dress shoes that manages to sell pairs for less than you might expect thanks to a direct-to-consumer sales model. The company encompasses all the major dress shoe styles, from Oxford to Derby to Loafers and Monk Strap, and with all pairs being handmade and incorporating a variety of construction methods, including both Blake and Welt, along with a combination of the two, you can be sure of a long-lasting pair that will look good for years to come.
Allen Edmonds
Born in America in 1922, Allen Edmonds decided to employ some new shoemaking techniques in a bid to create even more comfortable dress shoes. This saw the company do away with nails of any kind, as well as the metal bar that many other companies use under the instep. The decision continues to prove to be a successful one, with many claiming Allen Edmonds shoes to be incredibly comfortable. You'll find a range of styles and designs within the company's range, including Boulevard Cap and Wingtip Oxfords, along with a multitude of colours that will work with any suits you have in your wardrobe.
Cole Haan
American footwear giant Cole Haan is in the business of providing everyone with the perfect pair of shoes. With many pairs being available in extended sizes and widths, along with a variety of styles: Oxford, Loafer, Derby, and all pairs being ready to wear right from the off with no real break-in period required, they're proof you don't need to resort to centuries-old brands for great quality dress shoes.
Belsire
Belsire is another Italian manufacturer of high-quality leather dress shoes that belie their price tag. Belsire constantly strives to keep up to date with the very latest in footwear materials and production methods, to ensure the dress shoe needs of the modern man are consistently met.
Reiss
British fashion label Reiss nestles neatly in the space between high-street fast fashion and truly high-end designer, offering guys an affordable premium collection of clothes, accessories and footwear that favours neutral tones and plain designs across formal and casual pieces.
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
A name heavily associated with all things business and formal is Charles Tyrwhitt. The British label was founded on London's Jermyn Street and has since become a force to be reckoned with within the dress shirt space.
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 Baker
British luxury clothing brand Ted Baker has asserted its place within the fashion sphere through predominantly word of mouth, since there is no advertising. Ted Baker aims to inject humour into its pieces, along with other quirks such as coloured laces or interesting patterns and prints.
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
When you're an official supplier of footwear to the US Presidents, then you must be doing something right. That's certainly the case for Johnston & Murphy, a footwear and clothing company that can have its history traced back to 1850. In the 170 years since, Johnston & Murphy has continued to produce high-quality shoes made using traditional techniques that will be guaranteed to last you countless wears.
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.
J. Crew
Not just a supplier of shirts and chinos to preppy college boys, J. Crew completes the outfit with its own range of footwear. Select collections are made in collaboration with other well-known footwear brands, but J. Crew's solo efforts are equally appealing.
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.
ALDO
Canadian footwear retailer ALDO was founded in 1972 and has since cemented itself as a go-to destination for incredibly affordable shoes of genuine quality. Not all styles will be to everyone's taste, but versatility and the desire to want to include everyone adds to ALDO's appeal.
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
Doucal's is something of a revelation within the mens dress shoe industry. The Italian company was only founded in 1973, meaning several of its peers have at least 100 years head start, yet the brand has already cemented itself as one of the big players for men seeking formal footwear everywhere. Doucal's secret is combining the quality and comfort of Italian leather, but using it to create shoes in an unmistakably British way. After all, it's the Brits who have really put their stamp on the luxury footwear scene, and imitation is the sincerest form of flattery, right?
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.
Myrqvist
Swedish footwear brand Myrqvist employs a direct-to-consumer approach so that it can offer customers handcrafted dress shoes for a much more affordable price compared to its competitors. Leather and suede are sourced from France and the UK respectively, and all shoes are put together in Portugal.
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.
Lloyd
German footwear brand Lloyd was founded in 1905, setting up a factory in Sulingen, where it remains today. Each pair of Lloyd shoes is distuingished by a red stripe found on the bottom of the heel, a mark they have adorned since 1968. While Lloyd shoes aren't all produced by hand, they do at least get seen by real hands for the finishing process. However, the factory production method allows them to not only produce a varied and extensive range, but also allows them to be much more affordable than some other brands on this list.
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.
Carmina
This Marjorca-based shoemaker has been producing its eclectic range of dress shoes on the island since 1866. The fact the company is still going strong today should tell you all you need to know about the quality of the shoes that walk out of the factory. Carmina is dedicated to sourcing the finest quality leathers to use for all of its handcrafted shoes and as a strong supporter of the Goodyear welt, Carmina shoes will last you for many, many miles.
Grenson
Grenson was founded in the same year as Carmina, albeit in Northamptonshire, England. Although Grenson didn't adopt its company name until 1913, by then it was already well established and, like Carmina, was known for its commitment to using the Goodyear welt construction method, resulting in durable dress shoes that offered style and substance in spades. Grenson remains synonymous with luxury and quality today, and is best known for its use of brogue detailing across shoes and boots. In fact, it's hard to find a pair of Grenson shoes without the detailing, so if it's a formal pair of dress shoes that can be worn casually with jeans and a blazer you're after, Grenson is a tough brand to beat.
Crockett and Jones
Another prestigious shoemaker to hail from Northamptonshire is Crockett & Jones. The English company, like others on this list, has an illustrious history in the shoemaking game, having been founded in 1879. C&J specialises in Goodyear welted footwear and in a bid to retain its high-quality craftsmanship and reputation, remains family-owned to this day.
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.,
Paul Smith
Paul Smith is a British brand that can be consistently relied upon when it comes to quintessential British sartorial. Whether it be suits, shirts or shoes, Paul Smith has you covered for all bases. Paul's dress shoe range includes Oxford and Derbies and with them, you can expect 100 per cent leather and comfort guaranteed.
Tod's
Italian luxury footwear brand Tod's is perhaps best known for its range of high-end suede driving shoes and loafers, making it the go-to company for summer-orientated footwear.
Edward Green
Also muscling its way into Northamptonshire-based luxury shoemaking is Edward Green. Edward's shoes were favoured by the likes of Ernest Hemingway and Edward, the Duke of Windsor shortly after the company found its footing in 1890.
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.
Church's
Church's is certainly one of the more famous shoemaking companies to come from Northampton, and, likes its peers, was founded in the late 1800s. The company initially had workers producing shoes from their own homes before finally bringing production under one roof, and the company really found its footing when it launched an 'Adaptive' collection of shoes that offered customers the chance to essentially customer their dress shoes in various widths, materials and even half-sizes (something not offered by most other rival manufacturers).
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
Another brand sitting at the top end of the budget spectrum is John Lobb, but there's a good reason for it. The British company, which started life (and is still best known for) as a boot maker before expanding into dress shoes too, is a true master of its craft. Minute details on every pair of shoes, such as seamless back pieces and whole cut quarters only add to their luxurious nature, not to mention the use of Goodyear welts and hand-finished touches all over to leave you with a pair of shoes that will last numerous wears.
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
Founded in 2014, TAFT is a men’s footwear brand specialising in unique, bold shoe designs. TAFT shoes are produced in Spain and Portugal with premium textiles ranging from suiting wool, to woven upholstery fabric, to Charles F. Stead leather. Meticulous in their work, intentional in their designs, and obsessive over what makes the cut, TAFT has become well-known for their extremely well-made unique men’s shoes.
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.
Jack Erwin
Founded in 2013, Jack Erwin was launched with one sole purpose: to create truly timeless men’s shoes. Partnering with the finest factories and artisans in the world, creating custom styles, and eliminating costly markups and middlemen that drive up the costs of other quality dress shoes, Jack Erwin produces some of the best men’s footwear available that’s surprisingly affordable.
Modern yet timeless, Jack Erwin has a huge selection of men’s dress shoes that are refined, precise, and unadorned for an extremely reasonable price.
Ace Marks
Founded in 2012, Ace Marks believes that men shouldn't have to spend obscene amounts for a handcrafted world-class shoe. Using modern technology, to cut out middlemen and their markups, Ace Marks can directly deliver cleverly contemporary, utterly luxurious, and comfortable shoes (which rival those of the top luxury brands) all at an attainable price.
With a huge range of dress shoes - and with every style from monk straps to oxfords on offer - you’re sure to not only feel comfortable but also make a lavish powerful statement when rocking a pair of Ace Marks dress shoes.
