For generations, penny loafers have remained a go-to choice for footwear lovers who appreciate style, comfort, and versatility. These sleek slip-ons easily transition from professional to casual settings and work with nearly every item in your wardrobe—be it tailored pants, casual jeans, dresses, or skirts.

Let’s take a closer look at the origin of this classic shoe, explore the different variations available today, and dive into ideas on how to wear them with confidence.

Where It All Began

The beginnings of the penny loafer can be traced back to the 1930s, inspired by Norwegian slip-ons worn for leisure. Their appeal quickly caught on with American tourists and, soon after, U.S. brands made their own versions. One major innovator was John Bass of G.H. Bass & Co., who introduced the “Weejun” loafer featuring a distinctive leather strap across the upper. People started slipping coins into the strap’s slot—hence the term “penny loafer.”

These shoes saw widespread popularity through the mid-20th century, faded briefly during the more rebellious fashion wave of the 1970s, and returned stronger than ever in the 1980s thanks to the preppy fashion boom. Since then, they’ve remained an essential part of many wardrobes.

Varieties of the Modern Loafer

Classic Loafers
Timeless and polished, this style may feature subtle details like tassels or minimalist finishes and is often crafted from leather, suede, or textured materials.

Heeled Loafers
With added height, heeled loafers bring a modern edge and work beautifully for those who prefer something a little dressier. These shoes can range from subtle block heels to bold platforms.

Backless Loafers
Combining elements of loafers and mules, these are easy to slide on and great for warmer days. They’re often adorned with metallic accents, embroidery, or fun patterns.

Pointed-Toe Loafers
For a more refined silhouette, pointed loafers offer an elegant option. They work especially well with tailored outfits and can elevate even the simplest ensemble.

Style Pairings That Work

Trousers
For office-ready looks, pair a traditional penny loafer with tailored slacks and a structured blouse. Want something a little more contemporary? Opt for a heeled or pointed version with cropped pants for a sleek silhouette.

Jeans
Boyfriend jeans and loafers create a relaxed yet put-together weekend look. Skinny jeans pair well with sleeker styles like pointed or patent loafers. Add a graphic tee or moto jacket for some attitude.

Skirts
Knee-length pencil skirts or A-line styles look sharp with loafers. In cooler months, layer with tights and a turtleneck to complete the look.

Shorts
A tailored short with a button-down and loafers creates a smart summer outfit. For laid-back styling, go with Bermuda shorts and backless loafers for a relaxed daytime option.

Dresses
Structured wrap dresses or streamlined shirt dresses pair beautifully with loafers. Just avoid overly voluminous styles which can clash with the shoe’s minimalism.

Styling Suggestions for the Perfect Fit

• Always choose loafers that match the mood of your outfit—sleek versions for workwear, more casual styles for off-duty days.
• Make sure they fit snugly around the heel without slipping or feeling tight.
• If you have wider calves or feet, seek out designs with more room or opt for adjustable elements like elastic panels or lace detailing.
• Slimmer legs may benefit from loafers with decorative features to add volume visually.

Penny loafers have stood the test of time for a reason. Whether you’re dressing up for work or putting together a laid-back outfit for a weekend outing, they bring a balance of ease and sophistication that few other shoes can match. Dust yours off, or treat yourself to a new pair—it’s a timeless step in the right direction.