womens penny loafers black

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Womens Penny Loafers Black

Penny Loafer Style Guide: How To Wear & Best Penny Loafers

Though the prep sartorial tradition comes and goes in waves in America, it’s never really out of fashion. We often think of critter-laden trousers and boat shoes as typically preppy, and with good reason. Sometimes, though, we overlook a classic shoe that became popular with the preppy set and has since become a household name: the penny loafer.

In this guide, we’ll explore the Penny Loafers in detail including:

Beckett-Simonon-Cohen-Penny-Loafer-&-Box
wolf & shepherd banner

Quick Buyer’s Guide

Want to save time? Check out our quick buyer’s guide to shop our recommendations! You can also read about each of our top picks below.

Beckett Simonon

Beckett Simonon Cohen Penny Loafer

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Allen Edmonds

Allen-Edmonds-Addison-Penny-Loafer

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Wolf & Shepherd

Wolf & Shepherd Penny Loafer Shoes

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Maglieriapelle

Maglieriapelle handmade Cunda Tassel Loafers

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Paul Parkman

Paul Parkman Hand Painted Penny Loafer

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Mephisto

mephisto cap vert penny loafers

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What Are The Best Penny Loafers For Men?

Searching for the right pair of penny loafer shoes can be a pain. You can use the following links to jump to the best penny loafers to buy online or scroll down to read it all:

Best Penny Loafers

  1. Value For Money: Beckett Simonon Cohen
  2. Construction: Allen Edmonds Addison
  3. Comfortable: Wolf & Shepherd Ringer
  4. Painted Finish: Maglieriapelle Cunda
  5. Premium: Paul Parkman Penny Loafer
  6. Foot Conditions: Mephisto Cap Vert

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Related Shoe Styles

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What Is A Penny Loafer

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1. Beckett Simonon Cohen [Value For Money]

Beckett Simonon Cohen Penny Loafer

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Our current favourite penny loafers by a country mile, the Cohens by Beckett Simonon are elegant and well designed. Retailing at $200, they’re very affordable and constructed with a Blake Stitch.

Furthermore, you can benefit from an extra 20% discount with the code “BU20” during checkout!

Read More: Beckett Simonon Cohen Penny Loafer Review

2. Allen Edmonds Addison Penny Loafer

Allen-Edmonds-Addison-Penny-Loafer

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Allen Edmonds are a renowned American brand for providing excellent quality given their price point. The Addison is a little chunkier due to the Goodyear welted Dainite sole. However, they’re durable and will provide you with beautiful footwear for years to come.

Read More: Allen Edmonds Addison Penny Loafer Review

3. Wolf & Shepherd Ringer Penny Loafer

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For unparalleled comfort, we recommend Wolf & Shepherd, which has garnered quite the reputation. Although we have yet to review the Ringer, we have covered a number of other Wolf & Shepherd shoes and we admit that we’re converts!

4. Maglieriapelle Cunda [Handmade Loafer]

Maglieriapelle handmade Cunda Tassel Loafers

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Before you say it, these are indeed tassel loafers and not pennies. However, we struggled to resist the temptation to not talk about them here. These beautifully handcrafted loafers from Turkey are given a unique painted finish, which produces their deep colour. We love them in Forest green.

Read More: Maglieriapelle Cunda Tassel Loafer Review

5. Paul Parkman Penny Loafer [Premium]

Paul Parkman Hand Painted Penny Loafer

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Like the Maglieriapelle shoes above, these are handmade with a painted finish. Paul Parkman have a number of eccentric and exciting loafers in their collection. However, we’re particularly fond of this classic design that lets the leather quality and finish do the talking.

6. Mephisto Cap Vert [For Foot Conditions]

mephisto cap vert penny loafers

  • Colors: Black, Brown, Navy, Rust
  • Material: Leather
  • Pricing: $350 [Buy On Amazon]

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We’re normally not particularly fond of Mephisto’s shoe designs as they tend to be somewhat clunky or inelegant. However, the Cap Vert penny loafer is an exception and is perfect for men with foot conditions.

Top And Side View Of Penny Loafer

What Are Penny Loafers?

Penny loafers are laceless shoes with a moccasin-style upper that’s stitched to a separate sole and heel. They have a strip of leather called a “saddle” that sits horizontally across the instep. Nowadays, a broader definition can include any shoe that has such a strap, regardless of its construction.

The saddle is sometimes referred to as a “penny keeper.”

We will refer to this shoe as a “penny loafer,” “penny slip-on,” and “penny” throughout this article. More on that below.

History: G.H. Bass & American Style

In the mid-1930’s (some records say 1934, others say 1936), G.H. Bass put their own spin on Norwegian slip-on shoes, basically stitching a heel to a moccasin-style upper. They added a strap of leather across the upper vamp (referred to as a “saddle”) and sold them as casual house shoes. They called them “Weejuns” (to sound like “Norwegian”), and the term is still copyrighted by Bass today.

They became known as penny loafers, and they went from being “indoors only” shoes to being a workhorse of many gentleman’s casual wardrobes.

Why Are They Called Penny Loafers?

In the 1950’s, prep school students regularly wore Weejuns with their chinos and sport coats or blazers. The saddles of Weejuns had a diamond cut-out shape in the center, and it was common at the time for young people to put pennies there. It’s not exactly clear why this was a thing, but there are some theories:

  • Two pennies were all you needed to make an emergency phone call
  • Simply make a fashion statement
  • Pennies would bring good luck

The practice of putting pennies in the saddle of Weejuns led to the widespread use of the term “penny loafer.” In fact, Cole Haan, an American footwear brand formed in 1928, sold a penny loafer that came with actual pennies in them back in 2008 for their 80th anniversary. That’s about as #throwbackthursday as it gets.

Different Penny Styles

Not all penny loafers are created equal. Though there are different styles of shoes that incorporate a saddle, we will refer to them as either “penny” or “penny loafer” unless intentionally being more specific.

Blind Penny

Brown Blind penny Loafer

A blind penny is the same as a penny loafer, except for the fact that the diamond cut-out in the saddle’s center is either filled in or non-existent. It is thus referred to as a “blind” penny.

Aside from this small detail, a blind penny loafer shares all of the same characteristics as a normal penny loafer.

Beefroll Penny

Brown Beefroll Penny Loafer

This is a classic aesthetic detail typically seen on Weejuns and similar models. The plug (part of a loafer wherein the vamp is stitched to the sides) is exaggeratedly large and takes on the look of a beef roll.

It’s a casual, handsome detail that you won’t find on dressier slip-ons that have penny keepers.

Penny Slip-On

You’re probably asking, “Wait, aren’t loafers the same thing as slip-ons?”

Sort of, but not really. The difference hinges on how much influence a moccasin, the prototype for these two styles, has on their construction.

“Loafer” refers to a laceless shoe with a moccasin-style upper stitched to a separate sole and heel. “Slip-on” refers to a laceless shoe whose upper is not constructed like a moccasin. Slip-ons tend to be preferred by businessmen because they can be worn more easily with suits due to their dressier nature. A penny slip-on is simply a slip-on shoe with a penny keeper sewn onto the vamp.

Granted, “penny slip-on” isn’t an industry-wide term, but it’s a distinction that’s worth making. You don’t want to wear a penny loafer with a business suit, but you do want to wear a penny slip-on. Keep in mind that the shoe industry will refer to both styles as a penny loafer regardless of whether or not it’s technically correct to do so.

Penny Moccasin

Tan Penny Moccasin Shoe

Another term that doesn’t really exist in the footwear industry but should, a penny moccasin is simply a laceless, heel-less shoe with a saddle across the vamp.

Much more casual than the loafer or slip-on version, it’s on par with a driving shoe in terms of dressiness and construction.

How To Wear Penny Loafers

If our conversation includes moccasin, loafer, and slip-on versions, then you can safely wear any style penny with anything except a tuxedo.

Formality

Light Brown Penny Loafer
  • Jeans: Moc or loafer in any color. If jeans are dark and slim, a penny slip-on will work.
  • Casual Trousers: See jeans
  • Suits: If light or more summery, mocs and loafers will work without socks. If it’s a darker business suit, a penny slip-on will work well
  • Tuxedo: Don’t wear any style penny with a tuxedo

Seasonality

As penny loafers are available in nearly every color and material imaginable, they can be worn any time of year. Here are some suggestions for styles by season:

  • Spring: Loafer or moc in light brown/tan leather or suede, slip-on in British tan
  • Summer: Loafer, moc, or slip-on in white or bone-colored suede or nubuck
  • Autumn: Dark brown distressed leather loafer, varigated brown slip-on
  • Winter: Black or burgundy loafer or slip-on in leather or cordovan

Common Fit Issues

Everyone’s foot is built differently, and most people have some sort of irregularity with their feet. As it relates to penny loafers (or any laceless shoe that doesn’t use elastic in its construction), those with a high instep may have issues.

A high instep describes a foot in which the instep has a protrusion of some sort. This makes fitting certain shoe lasts uncomfortable. As loafers have little give, someone with a high instep will often have trouble wearing these comfortably. The saddle of a penny loafer simply applies more pressure on the instep, exacerbating the problem. The same issue applies to bit loafers.

This isn’t to say that a man with a high instep won’t ever be able to wear a penny loafer. It just means that you’ll have to try on a few pairs from a few different brands, and that may mean ordering a bunch online and returning those that don’t work. It may also mean spending a day out at some shoe stores trying on everything you see until your foot tells you, “Yes, these are the ones.”

Not a bad day, we think!

Do Pennies Belong In My Closet?

Every man, no matter what his job, age, or social circumstances should own a penny loafer. They are simply so versatile and classic that they offer some of the best return-on-investment that any shoe can offer.

If you don’t wear suits every day, make it one of the first pairs you buy and wear them with nearly everything. If you do wear suits every day, make them the third pair you buy, right after an oxford and a derby. You have to wear something on the weekends!

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.

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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.

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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.

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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.

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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.

business professional - Visit Stylishlyme.com to read what is not business casual

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.

How to wear jewel toned colors

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.

What to wear with leopard flats - Visit Stylishlyme.com for more outfit inspiration and style tips

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!

Store your on the go must-haves in style with a womens penny loafers invitation. Discover fashionable designs and vibrant colors to amp up your on womens penny loafers rotation. Whether you’re headed to the office or just running errands, on womens penny loafers at outlet invitation make perfect addition to your collection.

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