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Harry’s Footwear Fundamentals




Shoes are so fundamental to a man's wardrobe that it can be easy to overlook the details. But just because shoes are a necessity doesn’t mean a man shouldn’t think seriously about them. There is a whole range of classic, time-honoured dress shoe styles, from brown leather derbies to streamlined double-monks, that no closet is complete without.



How can you tell a classic from a flavour of the week? A great pair of shoes won’t only look sharp: it will keep looking great for years, immortal in fashion and built to last. “A timeless shoe isn’t just a fashion must,” explains Kevin Eisenberg, senior footwear buyer at Harry Rosen. “It’s also a great long-term investment.” A well-constructed, traditional shoe, properly maintained and made from the highest quality leather, can remain a wardrobe staple over a lifetime.


These five indispensable shoe styles are as versatile and timeless as they come. Here’s what to look for and how to identify each.


The Cap-Toe Oxford


A fixture of every traditional, well-rounded wardrobe, the cap-toe shoe is ideal for business-wear and the most formal of sartorial occasions. Unlike the more casual Derby, the Oxford style of dress shoe has its laces sewn closed, making for a tighter and more streamlined formal look. This cap-toe Oxford by Church’s is crafted from hand-selected leather in Great Britain, and is renowned for its sturdiness and durability. A first-rate pair of dress shoes like this will last forever and never go out of style.


The Plain-Toe Leather Derby


A more casual, modern alternative to the traditional cap-toe Oxford, the plain-toe leather Derby is the perfect shoe for formal and business settings that have the luxury of a little flair. In this deep, burnished brown, especially, the open-laced Derby style pairs beautifully with a navy suit, or even with a pair of slim-fitting, high-quality jeans. This superlative take by To Boot New York strikes just the right balance between classic and contemporary.


The Wingtip Brogue


By far the most distinctive iteration of the classic men’s dress shoe, the wingtip brogue is as elegant as it is eye-catching, standing out and looking on-point in equal measure. “Broguing” refers to the decorative perforations that run so strikingly across the shoe’s sides and toe, while “wingtip” is the name curved cap that runs across the toe and down along in “wings” on either side, which looks like a “W” from above. These dapper brown-leather lace-ups by Barker are a great take on a fabulous look, and will look spectacular dressed up with a suit and tie, or dressed down with raw denim.


The Penny Loafer


The classic penny loafer, a casual slip-on leather dress shoe marked by its unmistakable saddle strap where the laces ought to be, is among the most elegant shoes a man can own — a suave, elegant variation on the more conservative formal classics. You can’t go wrong with this simple, streamlined pair by Salvatore Ferragamo, made in Italy from the finest full-grain leather and hand-finished with jaw-dropping finesse.


The Monk Strap


There is no surer way to catch the attention of the office, the restaurant or the club than by wearing a pair of monk-strap dress shoes, which attract stares of envy and enthusiastic compliments like nothing else. That goes double, of course, for the double-monk: those two straps are as sophisticated and urbane as shoe details come, as seen on this slick brown-leather pair by Harry Rosen. With its decorative broguing on the toe — perfect to set off the streamlined silhouette — this is a classic shoe that will always seem on the cutting edge of fashion.