Are You Wearing The Right Pair Of Loafers?

Sitting in 2026, we might have grown tired of the quiet luxury era of fashion, but it did much to take men's footwear out of it's sneaker slump. Now, we don't have anything against sneakers at Esquire, but we do love ourselves a little bit of variety. And with the rise of preppy styles and boardroom fashion, shoes like the loafers, Mary Janes and boat shoes saw a huge comeback.

Except, some of these actually look really similar, to the point many don't know where the line lies between loafers and boat shoes. Or Tassel loafers and Kilties.

Types Of Loafers

Below, we explained the different types of loafers you would come across, where you should wear them and our best pick of each. 

Penny Loafers

Usually, when people say loafers, this is what they mean. This iconic shoe, featuring its distinctive strap and that little slit once meant for spare coins, has been a staple since the 1930s. Its timeless appeal still resonates today, making it a go-to for formal and semi-formal settings. Whether paired with jeans, chinos, or even a slightly wrinkled blazer, penny loafers strike that perfect balance of relaxed and serious. However, be mindful of their limitations – they might not fit in with a tux, and penny loafers with skinny jeans is a fashion faux pas.

Our pick: Ralph Lauren Maestra Calfskin Penny Loafer

Tassel Loafers

You realise how little details can make a big difference in footwear when you innocently wear a tassel loafer to a penny loafer event. It's easy to mistake the tassle as a mark for informality, these 50s slip-ons were the go to formal shoes for barristers, statesmen and businessmen alike. So a shining black tassle under a suit is the way to go when you want people to see you as the man who knows his formal shoes well.

Our pick: Brunello Cucinelli Leather Loafers

Horsebit Loafers

If you’re wondering why a Gucci shoe has it’s own category, then here’s why. The signature metal bar across the vamp, made famous by Gucci, became so popular when it was released that every other brand started adding bars to their loafers. The name stayed, and now every horsebit shoe made is a silent homage to Aldo Gucci’s design. These are loafers for your more formal, tailored ensembles.

Our pick: Gucci horsebit square-toe loafers

Monkstrap Loafers / Monk Shoes

The double monkstrap has become something of a calling card for menswear enthusiasts. Two straps, two buckles, and just enough edge to stand apart from standard lace-ups, it sits comfortably between formal and casual. It gained traction through blogs and online style communities, where it quickly became a default choice for anyone looking to signal a bit more sartorial awareness.

Our pick: Tramezza Double-monkstrap leather monk shoes

Kiltie Loafers

Unless you experiment a lot with your style, kiltie loafers can be a bit tricky. With that fringed leather detail, they offer a burst of texture and personality. Pair them with a clean, minimal outfit, and they add fantastic depth, kind of like wearing colourful socks under a suit. However, if your look isn’t cohesive or you wear them to the wrong date, they can also seem too frivolous for people to take you seriously.

Our pick: G.H.Bass Weejuns Layton Kiltie loafers

Driving Shoes

As the name suggests, these shoes are all about comfort and functionality. They look similar to a penny loafer, but are designed with soft materials and finished with rubber nubs for grip. They excel in scenarios like short trips, travel days, or quick errands. While they shine in these casual settings, trying to make them your all-day city shoe might leave you disappointed, as they can lack both structure and style for extended wear.

Our pick: Tod's Gommino Leather Driving Shoes For Men

Formal Pumps

Come on, you know these. Your dad wore it,, your grandfather wore it. With their sleek patent leather and minimalistic design, sometimes adorned with a bow, they’re distinctly for black-tie events. If you find yourself having them without adequate occasions to wear them, it might be worth reconsidering, as casual wear with pumps often appears forced. They serve a precise purpose as elegant footwear but aren't meant for everyday life.

Our pick: Christian Louboutin Dandydeco patent leather loafers

Boat Shoes and Espadrilles

Lastly, while boat shoes and espadrilles are often lumped in with loafers, they have their own unique charm. Boat shoes prioritise practicality, built for wet conditions with excellent grip in the sole. On the other hand, espadrilles capture the essence of summer with their breathable materials and rope soles. Both styles have their rightful place in your closet as the holiday shoes, but it’s key not to push them into situations where a proper loafer would excel.

Our pick: Loro Piana Sea-Sail Walk leather boat shoes