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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.

The Penny Loafer: A Guide to Wearing This Classic Shoe

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.

Now and then a classic footwear style comes along that really stands the test of time and loafer shoes are one of those classics we all have or have worn in the past. This shoe has seen little changes to the original design over the years yet it is more popular today than it’s ever been. With different designs available for both men and women this is still one of the top casual shoes out there. So what makes it so popular? How can it still be one of the most bought shoes on the market? Loafers are not only super stylish, there’re also super comfy too, what more could you want!

Our  post is going to answer all those important loafer questions you might have as well as giving you a little style know how when it comes to dressing this classic style up or down….

What Are Loafer Shoes?

Loafer shoes or slip on’s are generally thought of as casual shoes, they are low, lace-less shoes that were originally worn around the house by gentry and the royal family during the Summer months. Loafers are similar in shape to moccasins and are generally made of leather; they can be worn by men, women and children.

Loafers are often called Penny Loafers no one is 100% sure where this term for loafers came from but there are a few theories. One is that during the 1930’s pennies were kept in the diamond slit of the shoe in case the wearer had to make an emergency phone call. While in the 1950’s it was thought of good luck and good fashion sense to keep pennies again in the diamond slit. The term penny loafer is less commonly used today.

Loafers are generally thought of as a casual shoe however there is a loafer dress shoe that looks a lot smarter. These usually have a twin elasticated gusset to help the shoe fit better to the person wearing them and are made in the same shape as the classic Oxford shoe but without the laces, this style tends to be popular among businessmen and women in Britain. Loafers for children are usually worn for school as they are easy to get on and off and although they are a casual shoe they generally look smart.

Where Did Loafers Originate?

Back in 1847 a bespoke shoe company in London called Wildsmith Shoes developed the first ever loafer. The Wildsman Loafer was designed by Raymond Lewis Wildsman for King George VI as a casual shoe to wear around the house that later became popular with other royals and the land gentry.

Over in Aurland Norway a shoemaker by the name of Nils Gregoriusson Tveranger introduced his own loafer design in 1908 and he took it with him on his trip to America, where in the 1930’s the Spaulding family referred back to its design when they came up with their own. Loafers were popular in Europe and America and continued to be so until the late 50’s early 60’s. In 1966 however it had a bit of a fashion revival when Italian designer Gucci added a metal strip across the front, called a horse bit, this style is still very popular today.

Business men and women would wear this design throughout the 70’s while in the 80’s the loafer became an integral part of the Wall Street trader’s uniform as it was super comfy to wear in a demanding environment while still looking smart for meetings. When the 1990’s finally came around loafers were still being worn but they were not making as big a fashion statement as they once were and being worn mainly by college and school kids.

How To Wear Loafers: The Style & Fit

Looking back over the years there is not a fashion icon, be it man or woman whose wardrobe has not included a pair of loafers. Loafers can be worn at any time of the year but are often more thought of as footwear you would choose to wear during Spring Summer months. Yes they can be tricky to wear and yes it can be hard to know what to style them with but they really are a wardrobe staple.

If you can, always go for leather when it comes to loafers, they are more malleable which means more comfort for your feet and most importantly they will stand up better against the heat and no socks combination. Don’t go over the top with crazy prints and detailing, in the Summer choose soft pale shades in soft suede however once Winter come around play up to the dramatic weather by  going for a deeper colour and a more robust design.

Styling Loafers: Men

How to Wear Mens Loafers

For all you men the most important question when it comes to loafers is do I wear socks or not? Well that is entirely up to you, however if you do decide to ditch the socks, the Summer months are best to do so, you don’t want to get cold feet after all, choose linen trousers or chinos with tapered bottoms so that there is a nice gap between where your trousers end and the loafers begin. Once Summer has come around a casual pair of loafers will great with three quarter length shorts for days out.

If you have a special occasion such as a wedding or perhaps looking for a different office look, loafers work perfectly with a suit. Choose styles with fashionable details such as horse bits, which are the metal bar across the front or a dress loafer shoe which harks back to the stylish Oxford styles.

For Winter months they will look just as good with dark skinny jeans and a wool coat, be sure to brighten up a dull day by adding bright socks!

Styling Loafers: Women

Styling Womens Loafers

For women, loafers can add a smart preppy look that never goes out of fashion, it is true you can end up looking a bit like your gran but with a few style tips you can look super cool instead.

The most important thing to remember is to keep things simple with plain colours and classic detailing such as tassels, create an elegant, classic look that you can incorporate into any of your outfits. Work a retro cool look by styling a pair of tan loafers with fitted tapered trousers and a fedora hat; this would work well for an evening out with the girls or a gig. For an office ready look, a plain black style with metal plate will look fantastic with your skirt or trousers. Rock a preppy look by teaming a shift dress with a pair of loafers, your fit will love the comfort they give all day! In the hot Summer months team a pair of high waist smart shorts with some pretty pale loafers for a quirky look that will stand you out from the crowd or add some patent loafers to a pair of classic cigarette pants and striped top for a look that screams Parisian chic!

How to Wear Loafers: Socks Or No Socks?

The most popular question we keep hearing when it comes to styling loafers is, should we be wearing them with or without socks? The most important thing to take into account is obviously the weather, if it is cold outside going bare foot is going to uncomfortable and cold however in the Summer months it can really help keep feet cool and comfortable. So which is best?

Why not give some loafer liners a try, now don’t be fooled these are actually invisible socks not insoles, they are made to be worn with loafers so sit nicely inside your shoe without actually showing any of the sock, they give a fantastic impression of being bare footed without doing it.

There are also a range of socks out there can you could wear as an alternative, for example trainer socks sit very low down in the shoes so would work just as well. These all prevent excessive sweating, odours and also help keep the shoes from rubbing.

Wearing loafers without socks can be a bold fashion statement for men and women, always remember that if you are going sockless then keep your trousers fitted around the ankle to really maximise the look. Skinny jeans, chinos and cigarette pants will all give you the desired effect. For all you ladies out there, teaming your favourite sun dress with no socks can give you a bang on trend Summer look that never goes out of fashion.

Sometimes wearing socks can really help make a fashion statement, choosing bold eye-catching colours and funky patterns can add a quirky twist to your look while choosing frilly ankle socks gives your festival look a girly twist. It’s all about playing around and seeing what does and doesn’t work for you, have fun and mix things up.

Looking After Loafers: Cleaning & Care

Like all shoes, loafers need a bit of looking after when you are wearing them all the time and especially if you are wearing them without socks, which is why we have some little pearls of wisdom to share with you to help keep them in tip top condition for longer, don’t forget to check out our shoe care range here.

Firstly, cleaning your loafers, this all depends on the material, for example leather styles can be cleaned using a hard bristled brush and polish this will keep them looking as good as new and buff anyway any marks, don’t forget the water resistant spray. For patent styles a wet cloth or antibacterial wipe will quickly get them clean and looking sparkling again.

If your loafers get a bit muddy for any reason then they too can be cleaned very easily. Leave them to dry out in a cool place to allow the mud to dry before carefully using a knife to chip away the dried mud. For any nooks and crannies an old toothbrush will soon see away any dirt.

For those of you who have suede loafers investing in a suede protector spray will really help prolong the life of your shoes. For any dirt patches invest in a suede brush and simply use this in circular motions alongside warm water to help remove any marks. Another top tip is to use a pencil eraser; these are fantastic for removing those stubborn marks that water alone will just not budge.

The thought of cleaning the inside of your loafers might fill you with dread but it is relatively easy, every time you wear them give the inside a quick wipe with an antibacterial wipe before leaving them to dry, not got any wipes to hand? Kitchen paper and washing up liquid will work just as well. If they don’t help simply swap the insoles for a new pair.

Mixing a teaspoon of vinegar with water can really help eliminate dirt on the inside of your shoes too, use on a sponge as they are a bit more robust, once they are dry sprinkle a small amount of baking soda inside to help utilise any odours.

So there we have it, all you need to know about loafers! So whether you’re looking for some style tips, ideas on how to keep them clean or simply want to know more about this versatile style we have it all covered. Loafers really are a wardrobe essential that can be dressed up or down so play around and mix up your look!

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