‘Dress shoes’ is a catchall term used to describe the the wide variety of smart shoes typically constructed from one or more pieces of leather. You can think of them as any type of shoe you would wear with a suit or separates.
There is generally at least a degree of handcrafting involved in the construction of dress shoes, some more so than others, which is why the price tags for those styles on the luxury end of the spectrum can be pretty spicey.
Dress shoe brands are also often heritage shoemakers with a long and storied history, not least those from Northampton in the UK, widely regarded as the Mecca of traditional shoemaking (although the cobblers of the Veneto region in Italy would vociferously contest that).
There are of course many different types of dress shoe, each with its own sartorial code, but having at least some of these styles in your locker will go some way to affording you a well-rounded, versatile and sophisticated wardrobe.
Key Types Of Men’s Dress Shoes
The Oxford shoe is the classic dress shoe, and besides a few outliers such as opera pumps, it is the smartest of the bunch. More often than not, the Oxford comes in black, and features a closed lacing construction, unlike that of its more relaxed cousin, the Derby (more on that below).
The wholecut Oxford is an Oxford that has been cut from a single piece of leather, and while it might show off both the quality of hide and tanning prowess, as well as the shoemaker’s expertise, it is no more smarter than the cap-toe. It does however lend itself to unique patina techniques and thus can look very eye-catching.
Often confused with Oxfords, the Derby’s point of difference (also known as the blucher in the US, after the Filed Marshall of the same name who helped Wellington defeat Napoleon at the Battle of Waterloo) is all to do with the lacing.
Whereas the Oxford is constructed with ‘closed lacing’, the Derby features ‘open lacing’. All this means is that the flaps housing the eyelets are sewn directly onto the upper of the shoe, creating a sort of bed where the laces sit.
It’s for this reason that the Derby shoe is considered the less formal shoe since it doesn’t share the same sleek proportions around the upper as the Oxford. Still, we’d be nit-picking if we said that you could never wear Derbies with a suit – but generally speaking, the shoe is better off paired with unstructured blazers and tailored trousers.
An off-shoot of the Derby is what’s commonly referred to as the ‘suede buck’, or buck for short. This is simply a regular plain toe Derby but constructed in nubuck, hence the name.
The Monk Strap
Monk straps have seen a resurgence in popularity in recent years, helped in the main by regular appearances in best-dressed street style features from Pitti Uomo in Florence. In lieu of having laces, the monk strap comes in two formats – the single buckle and the double buckle, with the former being regarded as the smarter of the two.
The shoe typically takes the form of a cap-toe Derby, but is fastened with a buckle and strap device, with the buckle sitting on the outerside of the shoe. You can find quite a divergence in styles, from formal single-buckle styles with developed patinas, to quite relaxed double-buckle styles with thin soles.
They are both excellent styles to be worn with wool tailored trousers, or pleated cotton trousers with a roomy leg, but avoid the skinny cropped silhouette which for some unfathomable reason, always seems to choose the monk as its victim.
While the loafer in all its varieties is very often seen as a casual shoe, it nevertheless deserves a place on the dress shoe list. A slip-on by any other name, the origins of the modern-day loafer are thought to hark back to the moccasins worn by Norwegian fishermen when back in the warm confines of their homes.
It wasn’t until the 1930s that G.H. Bass realised the commercial value of constructing such a shoe for an American audience, and christened it the ‘Weejun’ in 1936.
Today’s loafers are a diverse bunch – with penny, tassel and horsebit styles being the most popular – but the slipper-like Belgian loafer is also currently experiencing a moment with sartorial types.
The loafer is best worn with a more relaxed tailored silhouette, making it an excellent summer option with light-coloured suiting and separates.
The term ‘brogue’ does not actually refer to the unique style of shoe, since a brogue can be both an Oxford or a Derby. Instead it refers to the decorative ‘brogueing’ or punched leather pattern that is applied to the shoe.
It’s said that brogueing was originally devised to aid the removal of water from sodden outdoor shoes, but suffice to say that today’s brogueing is pure embellishment.
There are different types of brogue styles you need to be aware of: the ‘wingtip’ brogue features a characteristic ‘M’-shaped pattern of brogueing on the upper and is usually applied to Oxfords. Similarly, the semi-brogue is a less decorative style which only sees the brogueing running along the seam of the toe cap. The ‘longwing’ brogue meanwhile sees the perforated detail go all the way back to the heel.
The less brogueing one can see, generally means the shoe can be worn more formally, i.e. with suiting. It’s why you will often see rugged outdoor boot styles come with elaborate brogueing details, while the smarter Oxfords only have a hint of it at the toe cap.
The Best Men’s Dress Shoe Brands
One of a new-wave of independent luxury shoemakers, Velasca works directly with artisans in Italy’s famed Marche region, which handcraft each and every one of its designs with meticulous attention to detail.
The brand’s dress shoe collection spans the full breadth of styles, with everything from formal Oxfords and patent opera pumps to smart-casual Derbies and loafers available in a variety of timeless colour ways and finishes.
With the finest quality vegatable-tanned hides, leather soles, full leather linings and Goodyear-welted or Blake construction (for easy resoling) all coming as standard, these shoes belie their comparitvely modest price points. Something that can be attributed to Velasca’s direct-to-consumer business model.
Like Velasca, Morjas operates a direct-to-consumer model, meaning it cuts out the middleman to offer high-end, handmade footwear for less.
The brand is proud of its manufacturing process, and rightly so. Each atelier it works with is based in Europe and goes through vigorous testing before it makes the cut. The majority of Morjas’ shoes are produced in its family-owned factory in the village of Almansa, Spain, which has been handcrafting shoes using the Goodyear-welted method since the 1920s.
As you would expect, the quality is second to none. Each pair takes eight weeks to make and involves over 128 steps, across 61 dedicated workstations, from the first cut to the last finish. The result is a meticulously crafted dress shoe that’s well worth the wait.
You need deep pockets to shop at Edward Green, but the Northampton-based shoe maker produces some of the most exceptional dress shoes in the world.
Handmade precision using only the finest calf leather hides, Edward Green’s reputation is peerless, and has been ever since it launched in 1890. Only around 250 pairs of shoes are completed each week, demonstrating the level of artisanship that goes into creating each Goodyear-welted pair.
With an eclectic range of luxury classics, Green is especially noted for its fine Chelsea Oxfords and Piccadilly loafers.
Crockett & Jones
Another of the Northampton legacy shoe makers, Crockett & Jones has been at the forefront of the British luxury shoe industry since 1879. Each pair of its shoes can take up to eight weeks to construct, with the complex handcrafted process having in excess of 200 separate operations.
Crockett & Jones has a broad selection that features all of the classic dress shoes and dress boots, each of which provide excellent value compared to some of the other specialist luxury makers on this list.
Its suede summer loafers are always on the money, but if you’re looking for a smart pair of Oxfords for business, you can’t go wrong with this Royal Warrant holder.
Baudoin & Lange
The resurrection of the Belgian loafer in recent years can be squarely put in the hands of Baudoin & Lange, which launched its now-iconic Sagan loafer back in 2015 and hasn’t looked back since.
Handmade in East London, the shoes are more slipper-like than loafer, such is their softness and degree of suppleness. As far as relaxed yet elegant summer shoes you can pair with linen or cotton tailoring, there is no better match.
One of a number of Royal Warrant holders on this list, and also from Northampton, Tricker’s was established in 1829, making it one of the oldest of the heritage British shomakers. That it is still at the top of its game nearly 200 years later tell you all you need to know about the quality of its footwear.
These days, it is perhaps most recognised for its superb boots, but that is not to downplay its excellent collection of Derbies, brogues and monks, all of which are constructed with meticulous attention to detail.
Founded by Italian Alessandro Berluti in 1895, Berluti originally started life as a leather shoe specialist and has since evolved into a globally recognised luxury fashion brand.
The company has never taken its eye of its footwear business, however, producing wholecut Oxfords of the highest order.
Berluti is renowned for its application of handpainted patinas, so if you are in the market for a truly unique dress shoe, then there are few better places to explore.
Joseph Cheaney & Sons
Northampton-based Cheaney & Sons was once wholly owned by fashion powerhouse Prada but has since been acquired by two brothers who have been determined to restore the shoemaker to former glories – which meant doubling down of the shoemaker’s handcrafted legacy.
Foremost among its shoe collection is Cheaney’s brogues and semi-brogues, all of which are handmade in the same factory the brand has been in since 1900.
While Cheaney & Sons used to be a Prada-owned shoemaker, Church’s very much is under the auspices of the Italian fashion giant, a move that has only improved the shoemakers range and imagination.
Of course, the Northampton-based brand still excels in making all the dress shoe classics, and while it has kept one foot in the traditions of the past, the other has been planted in the future, resulting in a number of excellent contemporary styles appearing in recent collections.
Santoni was Italy’s best-kept secret for many years after it was founded in 1975 by Andrea Santoni, but has thankfully found its way to discerning shoe fans all over the world.
Still family run, Santoni’s handcrafted styles are of exceptional quality and detail. While it produces all of the classic dress shoe styles, it is perhaps best recognised for its sublime double monks, which figures since the Italian tailoring style is that much more relaxed than its British counterpart.
Look out for the beautiful patinas on the polished leather versions, as well as woven leather and suede iterations that are ideal for matching with summer separates.
French heritage brand J.M. Weston was founded in Limoges in 1891 and to this day still makes all of its superb footwear there.
What really sets Weston apart from many of its other peers is its approach to the tanning of its leather, which incorporates an ancestral method that the brand has retained alongside more modern approaches.
The result is shoes finished with a stunning patina, personified by the brand’s Golf Derbies and wholecut Richelieu Oxfords.
Salvatore Ferragamo was a pioneer of shoe manufacturing, making his name among the Hollywood starlets in the 1920s thanks to his comfortable yet flattering styles which he made-to-measure.
The shoemaker returned to Florence, Italy in 1927, where the brand is still headquartered and from where the family-run legacy continues to grow. Although Ferragamo is perhaps better known for its women’s collection, the men’s collection is just as sublime, with a stunning array of Oxford and Derby styles alongside more fashion-forward monk straps and loafers.
By shoemaking standards, Scarosso is a mere baby, having been founded in 2010 by the German pair of Moritz Offeney and Marco Reiter. While the paperwork is all done in Berlin, everything else about Scarosso is very much Italian.
The shoes themselves are made in a number of family-run factories dotted around the Montegranaro region, a region famed for its luxury shoemaking heritage. Because Scarosso is direct-to-consumer, the brand can afford to provide excellent quality shoes at much more affordable prices, giving you a slice of Italian artisanal craft at a fraction of the cost.
In our experience (this writer owns a couple of pairs of Scarosso loafers), the company offers brilliant value for money right across its diverse collection of classic dress shoes.