If you’ve underestimated the importance of the right pair of fashion shoes (for men) can do to your outfit, you might want to think again. As Jennifer Lopez’s character Ramona says to Destiny (played by Constance Wu) in Hustlers, where enterprising ex-strippers find a way to work the system: “Anyone can own a nice suit. You want to look at their shoes, their watches, briefcases, their wedding rings.” It was a quick gauge for Lopez and company for separating the players from the wannabes, the men who had power versus the average dude.
The takeaway from all this—apart from maybe paying cash rather than just handing a hot girl your credit card—is that if you think people aren’t looking at your shoes, you’re wrong. We’ll say it again: Shoes are probably the single thing that can make or break an outfit. Never mind what you’ve got on from the ankles up; if the shoes aren’t good, don’t even bother. If it could spell the difference between whether or not J. Lo gives you the time of day, shouldn’t you be more discerning?
A good place to start would be to educate yourself on the tried-and-true—the best shoe styles from brands that have stood the test of time and remained a favorite of the distinguished set. These are the essential building blocks, so have a look and find out which ones speak to you.
1| Tod’s Gommino Driving Shoe
Nothing spells luxury like owning a pair of shoes made exclusively for driving—and the classic Il Gommino is the prototype for just that. With the suede sole protected by nothing more than 133 rubber pebbles, it’s almost maddeningly impractical; made for driving, lounging, and really not much else, but so comfortable all the same.
If you’re looking for a walking shoe, opt for the City Gommino, equipped with a rubber sole for extra sidewalk protection. It’s worth noting that Italian man of style and Fiat titan Gianni Agnelli regularly wore Gomminos, which is already a good reason to own a pair.
2| Gucci Horsebit Loafer
Thanks to the madcap maximalism of the current era under the creative direction of Alessandro Michele, Gucci has been the past few seasons’ “it” brand, a darling on the red carpet circuit. But if you think we’re going to recommend its chunky dad sneakers, not quite—we’re here for one of its more enduring models, which has remained largely unchanged since its 1953 debut.
The easy slip-on is meant to work just as well with jeans as a suit, and its golden horsebit, inspired by classic equestrian fashion, has become just as much a brand trademark as the red-on-green stripe or the interlocking Gs. And though it made an impact in its initial offering of classic black, nowadays, you can get it checked, monogrammed, or lined with fur, just the way Michele would want you to.
3| John Lobb Half Brogue
Here’s a riddle for fashion shoes for men: What’s dressier than a plain oxford, not as aggressive as a full-on brogue, but always 100-percent appropriate? The answer is the perfectly balanced, therefore perfect-with-everything creation of London shoemakers John Lobb: the half brogue.
Introduced at the 1937 Paris Exhibition, it’s a versatile dress shoe that looks timeless in either glossy leather or lived-in suede. The company has cemented its reputation as the cobbler to kings, prime ministers, businessmen, and the literati, befitting its headquarters’ location on the very spot that was once Lord Byron’s stomping grounds.
4| Salvatore Ferragamo Penny Loafer
If you prefer your slip-ons to be more minimalist and gracefully unadorned, Ferragamo has long been known for creating some of the most beautiful, classic, longest-lasting footwear around, and its penny loafers are definitely the prototype.
What it lacks in flash, it more than makes up for with impeccable craftsmanship and fine details—consider that each calfskin leather shoe undergoes 320 different phases and more than four hours of manual processing, all so that it will last you a lifetime.
5| Saint Laurent Chelsea Boots
Here’s our pick for the man who is decidedly a lot less country and a little more rock ’n roll—Chelsea boots are sexy, badass, and pair well with either slacks or jeans. Plus, thanks to the elasticated side panels, this is a boot you can easily slip into if you’re the kind of guy who doesn’t want to be bothered with shoelaces or buckles.
The ease of use was among the reasons why this style was supposedly favored by Queen Victoria, though it was the Mod set of ’60s London, known for frequenting the Chelsea neighborhood, that would give the boot its name. Plus, the Beatles wore them, which makes them the epitome of British cool.
And when it comes to fashion shoes for men, you can’t get any more rock ’n roll than Saint Laurent, a brand that counts Mick Jagger as a muse (he wore its pieces on this year’s “No Filter” tour) and that has Keanu Reeves sitting front row at its shows.
