Buying Guide on Best Classic Penny Loafers for Men

The iconic Penny Loafer was trendy shoes for both men and women alike. This casual slip-on shoe style is so flexible that it can be worn with trousers, shorts, skirts and even dresses! They’re used in boardrooms and schools all over the world and across cultures, and they’re a staple in my own wardrobe.

History of Penny Loafers

The Penny Loafer emerged in the 1930’s, influenced by the light, slip-on shoes worn by Norwegian farmers. Popular with both men and women, the simple charm of the loafer was that it was both convenient and clever. The penny loafers strap was originally a design element, to bring suspense to the otherwise plain silhouette.

One of the particular attractions of the Penny Loafers is that they can be used as both formal and informal dress for both men and women. From high-level attorneys and accountants to highly-dressed Yale students, the Penny Loafers has become a trend that defies subculture and has really stood the test of time.

How to wear Penny Loafers?

Penny loafers are extremely versatile shoes that can be worn all year round when combined with the right dress. Follow our top tricks to make sure you don’t fall on while you’re wearing these trendy slip-ons:

1. Rockport Men’s Classic Penny Loafer

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The Classic Loafer Penny looks so relaxed that you can’t believe it’s a dress shoe. This traditional men’s apparel shoe is as trendy and relaxed at a corporate gathering as it is worn barefoot. The Classic Loafer Penny is the right dress shoe for an office suite or a khaki for a dinner with friends.

This men’s leather dress shoe is made with a polyurethane outsole that helps provide durable shock absorption to help minimize foot fatigue, leather uppers that are easy to clean, and an EVA footbed that fits the form of the foot to help with a more personal fit.


  • Heel measures approximately 1″
  • Polished and refined, the Classic Loafer Lite Penny by Rockport was designed with comfort and style for any occasion in mind.
  • Upper made with smooth, easy to clean genuine leather.
  • Boasts added cushioning designed to help shock absorption in the heel.
  • Polyurethane outsole helps provide durable shock absorption to help reduce foot fatigue.

2. Nunn Bush Men’s Lincoln Classic Penny Loafer Slip-On

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Fashion is where you’re going to find it. Nunn Bush finds it surrounded by warmth, commitment to elegance, and a legacy of premium craftsmanship. Nunn Bush has been making shoes of unprecedented distinction since 1912. Nowadays, all Nunn Bush shoes are made of the same premium fabrics, specially picked leathers, and craftsmanship that go back centuries. It’s something you’re going to feel in the uncompromising fit, flexibility, and strength of all their sneakers.


  • Made with premium unlined smooth leather with authentic penny keeper and beef roll made this a true Classic.
  • A must-have for every wardrobe. Looks great with casual to dress attire.
  • Fully padded sock lining with Comfort Gel provides outstanding comfort right of the box. Can also be worn sockless.
  • Available in medium width and wide width for the perfect fit.
  • Nunn Bush is highly regarded as a premier footwear brand for providing the best value and style in fine men’s footwear since 1912.

3. ECCO Men’s Classic Moc 2.0 Shoes

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ECCO is a European shoe company founded in Denmark in 1963. Today, they own and run factories throughout Europe and Asia. They manufacture all the leather used to make Ecco shoes, taking care to protect the environment at the same time. Their only goal is to make a comfortable walking shoe.

ECCO crafts shoes to suit your needs, whether you’re scaling the stairs, wandering around the city all day, or strolling over rocky slopes; ECCO offers outstanding fit, reliability, protection, and versatility. Their innovative building methods and constant discovery of materials science add to the warmth you can count on. You’ll note the difference straight away and at the end of an exhausting climb, or after walking a dozen blocks uptown, you’ll begin to enjoy the ECCO difference.


  • Comfortable, casual moccasins in rich, premium leather that combine simplicity and elegance.
  • Leather lining – soft and comfortable with a perfect inner climate.
  • Removable leather-covered inlay sole with ECFS. ECFS increases air circulation for a perfect inner climate.
  • Cemented rubber outsole – the hard-wearing sole is flexible and soft.

4. Kenneth Cole REACTION Men’s Palm Penny Loafer

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  • EVA sole for comfort.
  • Comfort lining.
  • Comfort footbed.
  • Rubber sole.

5. Sperry Men’s Kennedy Penny Loafer

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For more than eighty years, Sperry has created a tradition of effortless heritage items. Whether for men, ladies, children, or infants, Sperry’s range of handmade accessories includes our famous Sperry boat shoes, sandals, loafers, flats, slippers, espadrilles, trainers, sneakers, and oxfords. Accessible in an inspired variety of colors, designs, and fabrics, our iconic shoes cross borders and cover centuries and genders with a mutual dedication to consistency, durability, and comfort. Ours were the initial prep symbols, as they have been since 1935.


  • Shaft measures approximately low-top from arch.
  • Materials Rich leather and nubuck are upper for texture and supreme durability Classic penny keeper detail.
  • Comfort Plush foam blown rubber outsole is super lightweight.
  • Traction Patented Razor-Cut Wave-Siping on non-marking rubber outsoles won’t scuff floors but gives you sure footing, from the boat deck to back deck.

6. Florsheim Men’s Jenson Penny Loafer Slip-On Loafer

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In 1892, Milton Florsheim started making shoes in a small factory in Chicago, Illinois. The first pairs of Florsheim shoes made by Milton and his father, Sigmund, were a remarkable mix of elegance, comfort, and high-quality workmanship. This legacy continues today with the Florsheim family’s dedication to creating trendsetting, high-quality boots. Florsheim shoes are still offered in a wide array of styles and widths.


  • Leather penny moccasin with classic driver shoe style details.
  • The uppers are genuine leather. The linings are leather and the sole is durable, lightweight, and flexible rubber.
  • The insole has a cushioned leather heel pad. Soft leather upper and comfortable rubber sole for long-lasting comfort.
  • Available in medium widths and wide widths.

7. JOUSEN Men’s Loafers Casual Slip On Penny Loafer

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  • Premium synthetic material in penny loafer stylish design.
  • Using standard US size makes this penny loafer easy to slip on and off.
  • The skin-friendly lining and cushioned latex insole make this casual loafer comfortable.
  • Suitable for casual, driving, working, you can wear it to formal occasions, like church, prom.
  • Slip-resistant and shock protection of the ankle are provided by these slip-on driving shoes.

8. Deer Stags Men’s Fund Classic Dress Comfort Penny Moc Loafer

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Master a classy look with the Penny Loafer of the Deer Stags Fund. The rich synthetic leather top is softly burnished for a classy appearance. A simple type of slip-on. Breathable fabric linen helps wick moisture for added warmth. Lightly cushioned footbed for all-day wear.

  • Master a classy look with the Deer Stags Fund penny loafer.
  • Rich synthetic leather upper is lightly burnished for a classy look.
  • Breathable fabric lining helps wick sweat for extra comfort.
  • Lightly cushioned footbed for all-day wear.

9. Rockport Men’s Shakespeare Circle Penny Loafer

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Rockport has been driving the busy days since 1971 when we made dress shoes very comfortable by incorporating sports technology to the style – the very first company to do so. Today, we’re going to push the boundaries to offer you the perfect balance of comfort and style.

Step up your khakis and cords with this handsome Rockport Penny Leather Loafer. The classic-looking upper features moc-toe stitching with a folding neck, back reinforcing, and standard vamp detail. The cushioned insole guards against impact, while the durable rubber sole provides traction and toughness.


  • Heel measures approximately 1″.
  • Platform measures approximately 0.5″.
  • Penny loafer featuring moccasin-stitched toe and fold-over collar with the reinforced counter.
  • EVA helps provide lightweight shock absorption to reduce foot and leg fatigue; Flex grooves in the outsole provide forefoot flexibility.

10. Cole Haan Men’s Pinch Penny Slip-On Loafer

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Smooth burnished calfskin uppers with a penny slot detailing give this shoe a polished look that looks very nice with anything from casual to formal wear. The fully padded leather cuff liner provides softness and makes these loafers comfortable enough to be worn without socks. The outsole gives this casual shoe the utmost in cushioned comfort. This comfortable slip-on shoe has a classic suede buffed outsole an injected thermoplastic urethane (TPU) pod and a low heel for stability. Genuine hand-sewn on-the-last fabrication of our legendary Pinch moccasin.

Today, Cole Haan carries this heritage to all of its brands, including men’s and women’s apparel and casual boots, ties, hosiery, handbags, small leather goods, outerwear, and sunglasses.


  • Heel measures approximately 1″.
  • Moccasin-toe penny loafer with stacked heel.
  • Perforated footbed.
  • 100% Leather.

What are the other ways you can wear Classic Penny Loafers

The outfit options are endless, but here are a few enjoyable and trendy examples of wearing loafers for your current wardrobe.

Penny Loafers with Pants

The iconic Penny Loafer is a basic work place for both men and women. Fit with a pinstriped wool trouser and a button-down shirt. Instead, slip into a pair of heeled pennies loafers.

Take a comfortable pair of silk or cotton ankle pants and slip on a pair of backless loafers or point-toe loafers. Wear a plain blouse, ankle trousers and trendy black patent leather point-toe loafers that bring a bit of drama to an otherwise casual look.

Penny Loafers with Jeans

The mild chunkiness of the penny loafer matches very nicely with the boyfriend pants. Add in a lightweight jumper and a stylish t-shirt, and you’re primed for a relaxed day out. A pointed toe loafer or lighter-weight classic loafer is ideal for slim denim. Think of animal printing or enjoyable embellishment for any drama. Attach a graphic t-shirt and a leather jacket and meet your mates for the lunch-and-shop date.

Penny Loafers with Skirts

This may be a tougher look to pull off for some, but proportion is the secret. Stick to the skirt that reaches the knee just over it. A classic pencil or A-line fits well as a shorter mini skirt.

Pleated skirt with a traditional penny loafers is best one, but a nice herringbone pencil skirt, a cashmere turtleneck and some sort of loafer is also a good combination.

Penny Loafers with Shorts

Yeah, you should wear short loafers! Try a chic linen short with a silk-down blouse and a pair of pointed-toe flats. It’s great for brunch. For a relaxed look, combine some Bermuda shorts with a vibrant floral top and some cotton loafers or embellished backless loafers.

Final Thoughts

We hope you liked this article and heard a bit about the shoes that you might be wearing right now. Best Penny loafers are always the perfect way to wear with all your dresses. Share your thoughts in the comment section below.