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Gentleman’s Guide to Style Loafers for an Old Money Look

Loafer shoes are a hallmark of refined elegance and timeless sophistication and are one of the most important parts of any ‘Old Money’ look.

From the iconic Penny to the esteemed Gucci and beyond, all types of loafers depict a sense of stylistic discernment, refined taste, and Old Money charm.

However, each loafer type is best styled in a particular way according to the shoe’s history and origins, each look depicting a distinct sense of heritage and luxury.

What Are Loafers?

As you’re about to find out, what does (and doesn’t) constitute a loafer is down to the exacting details.

First things first, let’s break down and discuss the key characteristics of a loafer.

  • No Laces – Ultimately, a loafer has no laces; in other words, it’s a slip-on shoe.
  • Open Ankles – A loafer is a “low shoe,” meaning that the ankle is exposed, and the shoe does not wrap snugly around it.
  • Small Heels – Loafers typically feature heels with a relatively low profile.
  • Decoration – Loafers will usually feature some decoration across the vamp, such as a saddle, tassel, or horse bit.

How to Wear Different Types of Loafers

Penny Loafers

The Penny loafer is the American Preppy take on this classic shoe design, recognizable for the diamond-shaped saddle (the leather strip sewn across the upper), perfect for slipping in a penny, hence the shoe’s name.

The Penny loafer shoe was popularized by the ‘Ivy League‘ students as a traditional yet comfortable shoe ideal for the blends of casual and formal attire depicting the collegiate look.

  • Formality: Formal, Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Spring, Summer, Autumn

Bit Loafers

A creation of Aldo Gucci, the Gucci loafer or the Bit loafer, named after the horse-bit snaffle, is recognized by the golden metal detail across the vamp.

Keeping with the company’s saddle-making heritage and Gucci’s love for the equestrian style, in 1968, he replaced the horizontal leather strap with gold hardware in the shape of two rings with a linked bar across.

The style was a hit with politicians like Richard Nixon and George Bush Sr., Hollywood stars like John Wayne, Jane Birkin, Brigitte Bardot, and Clarke Gable, and became the business shoe of Wall Street.

  • Formality: Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Spring, Summer

Kiltie Loafer

The Kiltie loafer has a decorative fringed tongue overlaying the instep, a design inspired by the kilt, a traditional Scottish dress, hence its name.

Popularized by country club golfers, Kiltie loafers have a flair reminiscent of Scottish golfing greens and are the ideal footwear for creating British Old Money looks (aka Sloane Ranger).

  • Formality: Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Autumn

Belgian Loafer

The Belgian loafer was invented in the 1950s by Henri Bendel, whose family store brought Chanel, Dior, and Balenciaga shoes to the U.S.

Compared to the sturdy Penny loafer, the Belgian loafer style has a soft construction, a one-piece apron on top of the vamp, and a small, decorative bow.

A delightful nod to European craftsmanship, the Belgian loafer has recently experienced rising popularity.

  • Formality: Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Spring, Summer

The Saddle Loafer

The Saddle loafer has a strip of leather that runs across the vamp and tongue of the shoe, Similar to a Penny loafer.

However, instead of stopping at the moccasin-like apron, this leather ‘saddle’ continues to the loafer’s waist and sole.

  • Formality: Formal, Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Summer, Autumn

The Butterfly Loafer

The Butterfly loafer takes its name from the symmetrical shape created by the two overlapping leather pieces, resembling a butterfly’s wings.

The bold design makes the Butterfly loafer one of the most casual shoes in this style, regardless of the colour or leather choice.

  • Formality: Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Summer, Autumn

Tassel Loafer

Considered a more formal version of the Penny loafer, the Tassel replaces the saddle – horizontal strap across the vamp – with decorative tassels dangling from the top, hence the shoe name.

These dress shoes were popularized by Prep school and Ivy League students as shoes ideal for elevating smart casual outfits and perfect for business casual settings.

  • Formality: Formal, Semi-Formal, Casual
  • Everyday wear: Yes
  • Season: Summer, Autumn

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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