Penny Loafers: Timeless Style for the Modern Man

Way back in 1980, a book appeared on shelves at stores around the country. It was supposed to be a bit of a joke. And it was. But it also became a serious guide to how many young people of that time decided to dress.


The Official Preppy Handbook” was a satire about how very rich and very elite people dressed. Remarkably, it also became a sort of how-to guide for strivers and the less-than-wealthy to look like they belonged at the top of America’s wealth period.


Central to the Handbook’s advice was that both men and women embrace the penny loafer. And it would appear that some 40 years later, that advice is once again popular. The penny loafer is back. And just like in the Handbook’s heyday, the penny loafer is once more seen as a signifier of wealth. Or perhaps of aspiring to have wealth.

The Official Preppy Handbook
Image by New York Times

“There's an old money trend going on now in guys’ clothes,” says Aisen Li, the Asian Dating Coach of Instagram fame. “It’s just simple, classic looks like penny loafers.”


Also part of that trend are other staples of the prep-school lifestyle, such as cardigans and knit polo shirts .


Aisen is a fan of the trend, saying it can work for many guys, and not just the already wealthy. Rather, penny loafers are a good choice for guys who “aspire to generate wealth,” he says. Wearing penny loafers can convey the message that “maybe I don’t have a trust fund, but I am ambitious.”

ivy style with penny loafers
Image by Gabucci & Septiemelargeur

History of the penny loafer

Penny loafers didn’t get their start in the “The Official Preppy Handbook.” They debuted about a half century earlier. Originally designed as a casual shoe for American prep school students in the 1930s, penny loafers have since evolved into a versatile wardrobe staple that can be dressed up or down for any occasion.


In this guide, we'll delve into the timeless features of penny loafers, explore how to style them for various occasions, discuss seasonal adaptations, share tips for accessorizing, and provide essential maintenance and care tips.

Classic Penny Loafer Features

Penny loafers are characterized by their slip-on design and distinctive strap across the vamp, often adorned with a small decorative slit or "penny" insert. This classic feature gives penny loafers their signature look and sets them apart from other types of loafers. Additionally, penny loafers typically feature a low heel and a sleek, almond-shaped toe, creating a timeless and sophisticated silhouette.


Note, however, that the Handbook was adamant that the truly wealthy do not put a penny in the penny slot. So you may want to keep your pocket change in your pocket.

Penny Loafers with details
Image by Caroline Weaver

How to Style with…



Business Casual: 


For a polished yet relaxed office look, pair your penny loafers with tailored trousers, a button-down shirt, and a lightweight blazer. Opt for classic colors like brown or black for a professional vibe that still exudes effortless style.

Business casual with penny loafers
Image by Pinterest

Smart Casual:


Elevate your weekend attire by pairing your penny loafers with dark denim jeans and a crisp white shirt. 


Add a leather belt and a stylish watch for a refined yet laid-back ensemble that's perfect for brunch dates or casual outings.


Smart casual with penny loafers
Image by Second Button

Formal Occasions: 


While penny loafers may not be the most traditional choice for formal events, they can still be dressed up for special occasions. Pair them with a well-tailored suit in a complementary color and opt for sleek, minimalistic penny loafers in polished leather for a sophisticated touch.


Formal occasions with penny loafers
Image by Ask the Gentlemen

Styling Penny Loafers in Different Seasons

The Handbook advised that penny loaders were for summertime. But penny loafers are a versatile footwear option that can be worn year-round with the right styling.


During the warmer months, opt for penny loafers in breathable materials like suede or canvas to keep your feet cool and comfortable. Pair them with lightweight chinos or linen trousers for a relaxed summer look.


In the cooler months, transition to penny loafers in rich, textured leather to add warmth and sophistication to your ensemble. Pair them with wool trousers or corduroy pants for a cozy yet stylish look that's perfect for fall and winter.

Seasonal styling with penny loafers
Image by The Second Button

Accessories to Enhance the Look

Accessories can elevate your penny loafer ensemble to the next level. Add a leather belt in a complementary color to tie your look together and opt for a stylish watch or bracelet for added flair. Don't forget to polish your penny loafers regularly to keep them looking shiny and well-maintained.

Maintenance and Care

Proper maintenance is essential to ensure your penny loafers stay looking their best for years to come. Regularly clean and condition your penny loafers to keep the leather supple and prevent cracking. Invest in a high-quality shoe horn to help preserve the shape of your loafers and avoid creasing.


Store your penny loafers in a cool, dry place away from direct sunlight when not in use, and consider using shoe trees to help maintain their shape and absorb moisture. Periodically polish your penny loafers to keep them looking shiny and new, and don't forget to protect them from rain and moisture with a waterproofing spray.

Penny loafers care and maintenance
Image by From Squalor to Baller

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