The Penny Loafer: A Guide to Wearing This Classic Shoe

For 80+ years, the classic penny loafer has been fashionable footwear for men and women alike. This comfortable slip-on style of shoe is so versatile that they can be worn with pants, shorts, skirts, and even dresses! They are seen in boardrooms and classrooms across the world and across cultures, and are a staple in my own closet.

The penny loafer can be worn on a relaxing Sunday afternoon or to a hectic Monday morning business meeting. The loafer has changed colors, material, heights, and weight over the years but has never lost its popularity. Now you can buy one with rhinestones or with sequins, they can be made of suede or snakeskin, it’s all up to you and what fits with your wardrobe.

Let’s take a look at a bit of history, the various types of loafers available, a well as some outfit examples to make this classic shoe a stylish addition to your everyday wear.

• Save

HISTORY OF THE PENNY LOAFER

In the 1930s Norwegians were producing leisure slippers (moccasin style) and began exporting them to the rest of Europe. Americans visiting Europe at the time started purchasing them and they started picking up in popularity. But it wasn’t until Esquire magazine featured them in a layout that these slip-ons became known to the masses in America.

Shortly thereafter, the iconic penny loafer was born and made popular by John Bass (of G. H. Bass & Co.). He took that simple slip-on shoe and added a piece of split leather across the bridge of the foot and named them Weejuns. Wearers began adding a decorative touch to the split in the leather, primarily with pennies…and the penny loafer was born.

Fun Fact: According to Zappos, “When pay phones were still ubiquitous and hadn’t yet been raised to a quarter, the penny loafer was often the source of funds for an emergency phone call home.”

While the penny loafer was one of the most popular shoes from its inception into the 1960s, they fell out of favor a bit in the 1970s (not exactly hippie footwear), but made a resurgence in the 1980s, as part of the “preppy” fashion craze. They’ve remained a staple ever since and versions can be found from even top designers like Gucci, Fendi and Prada.

The original penny loafer was made of leather, primarily black or brown, but has expanded over time. You can now find them in almost any color in leather, suede, patent leather, and vegan-style leather. Defined as a shoe that has no buckles or laces, the penny loafer—and loafers in general—are slip-on shoes with a rounded toe, with or without side gussets.

TYPES OF LOAFERS

In addition to the ubiquitous penny loafer, there are a variety of other loafer styles that have evolved over time.

The Classic Loafer

This shoe has the same silhouette, but without the split strap and penny. While some will have a smooth bridge (think: driving loafers, also called driving moccasins), oftentimes you will find the bridge of the loafer decorated with embellishments like tassels, bows, and even faux buckles.

Unlike its penny-loving cousin, a classic loafer can come in animal print, stripes, polka dots, paisley, and a number of other prints and patterns. In addition to traditional leather, you might find them in snakeskin, crocodile, or other exotic leathers, as well as cotton and less traditional shoe materials. Shop Penny Loafers Here.

shop classic loafers

• Save

Heeled Loafers

While loafers are traditionally a flat or low-heeled shoe, women have the advantage of adding heels to loafers. You can find those classic penny loafers with heels, ranging in height from one inch to four inches or more (with a platform). You’ll also find chunky-heeled loafers with fringe or embellishments. Shoop Luxury Heeled Loafers Here.

shop heEled loafers

• Save

Backless Loafers

Backless loafers are also a common occurrence. These are hybrids of a loafer and a mule (also called a slide). Like their heeled sisters, backless loafers come in the classic penny, with fringe or embellishments, and in a variety of materials and prints or patterns.

shop backless loafers

• Save

Pointed-Toe Loafer

The loafer has evolved over time, and for women it has been feminized with a pointed toe, to resemble more of a pointed toe pump. Also referred to as a pointed-toe smoking slipper, I’m particularly fond of these bronze loafers, which take a pair of jeans to the next level.

You can find pointed toe loafers in the same materials, prints, and with similar embellishments as the classic loafer described above.

shop pointed-toe loafers

• Save

HOW TO WEAR PENNY LOAFERS: OUTFIT EXAMPLES

The outfit combinations are limitless, but here are a few fun and stylish examples of wearing loafers with your existing wardrobe.

Pairing Penny Loafers with Pants

The classic penny loafer is a workplace staple, for both men and women. Pair them with a pinstriped wool trouser (with or without cuff) and a button-down shirt and you have a perfect office combination! Used to wearing heels? No problem. Step into a pair of heeled penny loafers instead.

Take a nice pair of silk or cotton ankle pants and don a pair of backless loafers or pointed-toe loafers like I have here. I’m wearing a simple blouse, fitted ankle pants and stylish black patent leather pointed-toe loafers, which add just a touch of drama to an otherwise business casual outfit. I like that the black tote has two different finishes, reflecting the matte of the pant and shine of the shoes.

• Save

Pairing Penny Loafers with Jeans

The slight chunkiness of the penny loafer pairs really well with boyfriend jeans. Add in an oversized sweater and comfy t-shirt and you’re ready for a casual day out.

For skinny jeans, a pointed toe loafer or lighter-weight classic loafer is perfect. For some drama, think animal print or fun embellishment. Add a graphic t-shirt and leather jacket and meet your friends for that lunch-and-shopping date.

• Save

Pairing Penny Loafers with Skirts

This can be a harder look to pull off for some, but proportion is the key. Stick to a skirt that hits at or above the knee (no mid-calf or maxi skirts). A classic pencil or A-line works well, as can a shorter mini skirt. I always think of a plaid pleated skirt with a classic penny loafer, but a nice herringbone pencil skirt, cashmere turtleneck and any type of loafer (with tights) is also a good combo.

Pairing Penny Loafers with Shorts

Yes, you can wear loafers with shorts! Try a tailored linen short with silky button-down blouse and a pair of pointed-toe flats. Perfect for brunch. For a more casual look, pair some Bermuda shorts with a colorful floral top and some cotton loafers or embellished backless loafers.

Pairing Penny Loafers with Dresses

I think it pays to keep it somewhat classic here. Don’t do body-con or really full-skirted dresses with loafers. Best to leave the empire waist or pouf dress in the closet. A simple little black dress and embellished loafers are perfect for almost any occasion. Try a summer shirtwaist with some colorful pointed-toe loafers, or pair a classic wrap dress with a classic heeled loafer.

• Save

I hope you enjoyed this post and learned a little something about the shoe that you may be wearing right now. I love fun historical facts about fashion and how the items we wear today have evolved over the decades.

And don’t forget to send me a post of you rocking your classic penny loafers!

-V