Twice a year for four days, sartorially-inclined gentlemen make their biannual pilgrimage to Pitti Uomo. These peacocking men turn the sidewalks of Florence into a runway with their masterfully-tailored suits and footwear.

The fashion-forward elite will show up with their bespoke loafers without so much of an adjustment to their pocket squares. To help you get started on improving your shoe game, here is the guide to loafers you never knew you needed.

Loafers are the quickest solution to get you out the door if you’re late or in a hurry. Just slip them on and off you go. There are four major loafer styles: the penny, horsebit, tassel, and Belgian. What sets them apart is their decorative feature, ranging from a little tassel, a metal horsebit, or a plain old strap.

A common misconception is that you can call loafers moccasins and vice versa. While the two have similar silhouettes, they are quite different. Loafers have a signature low heel, where the moccasins do not – the trademark studded sole of Tod’s moccasins has rubber studs that are there for added grip while driving, and it’s not a definitive feature of moccasins.

When putting on a pair of loafers, remember this rule of thumb: your trouser’s hem should end above the loafer, and don’t let it sag over the tongue.

1
Penny Loafers

The classic loafer as we all know and love was once the footwear worn by dairy farmers. The penny loafer is distinguished by the strap that runs horizontally across the vamp with a lip-shaped cut. Its history is also particularly fascinating: this style of loafer originated as the Bass Weejun (the latter being a play on ‘Norwegian’), before being adopted by the Ivy League prep-squad that sent it globally as they graduated in the 1950s and 60s.

How to wear them: They can pair with virtually any outfit for any occasion, except where it comes to black-tie events where some discretion should be had.

Prada Spazzolato Penny Loafers, £790 (S$$1,443), mrporter.com

2
Tassel Loafers

If you want to add a little flair to your ensemble, slip on these tassel loafers. This style is defined by decorative tassels (usually the ends of leather laces) that hang from the end of the vamp. Just look towards the ground at any Pitti Uomo season and you’ll spot at least one dapper gent sporting these loafers. But it isn’t the Europeans who invented the tassel loafer, with its history being credited to the Alden Shoe Company back in the 1950s.

How to wear them: While tassel loafers in burgundy are a classic, switch things up by opting for suede or velvet. It’s also slightly dressier, so while it is appropriate for business casual events, keep it in the rack when headed for a job interview.

George Cleverley Adrian Burnished-Leather Loafers, £468 (S$855), mrporter.com

3
Horsebit Loafers

Even as creative directors change, one thing at Gucci has remained steadfast for five decades: the horsebit loafers. Worn by the likes of John F. Kennedy, Brad Pitt, and A$AP Rocky, the iconic shoe is also part of the Metropolitan Museum of Art Costume Institute’s collection.

While the Italian house has since evolved its design to incorporate many other features (including a collapsible heel!), all of them bear the signature burnished-gold horsebits that make it recognisable even from a mile away.

How to wear them: The horsebit loafer provides a versatility that lets you pair with a three-piece suit and you’d still look formal. Of course, you can also just wear it with a shirt and trousers (socks optional).

Gucci Horsebit Leather Loafers, £481 (S$879), mrporter.com 

4
Slipper Loafers

No, these aren’t the same as your beach-ready Havaianas. Slipper loafers can very well stand in a category of their own. They can be ultra formal and black-tie ready, like this pair of Lanvin velvet slippers here. Or they can be your everyday slip-on in the springtime.

The great part about slippers is that you can easily customize them with a crest or your initials, making them truly your own.

How to wear them: If you’re sporting a pair of classic velvet slippers for a formal event, socks can be worn, especially if your trousers end below your ankles. Otherwise, leave the socks at home and show off your bespoke shoes. You’ve earned it.

Lanvin Velvet Slippers, £334 (S$611.26), mrporter.com

Josiah Neo
Writer
Josiah Neo is a tech writer who contributes occasionally to the fashion, travel, and culture beats. When he’s not busy keeping up with the keynotes, he’s probably stuffing his face with the best Melbournian donuts (at Shortstop, BTW) or watching his favourite esports team, the Los Angeles Valiant, pummel their opponents into oblivion.