Penny loafers are no longer only for backpack-wearing students in uniforms. In fact, classic loafers have been reinvented. But before we go into how to wear women’s loafers today, it would be worth your time to learn a little about their history and how they’ve lasted as a popular shoe through the years.


History Of Women’s Loafers

The name loafer itself essentially refers to a lace-free, slip-on shoe. Slip-on shoes have been around for centuries. However, according to Wikipedia, ‘Weejun’ (short from ‘Norwegian’) loafers were reportedly created back in the 1900’s when students traveling to Scandinavia saw fisherman wearing a simple style of loafer made like a moccasin. The style was brought back to North America where it started to get attention.

G.H. Bass then founded a company by his own name in 1876 and in 1936, they became the first company to market the ‘Weejun’ loafer style to the masses. They later trademarked the name. They added a strap running horizontally across the loafer vamp to add style. Because of the small opening in the middle of that strap, it seemed to be the perfect place to put a penny. That brings us to the penny loafer!


It is believed that penny loafers actually got their name back in the 1900’s when moms were looking for an easy place for their kids to keep extra change for when they needed to make a phone call. Believe it or not, phone calls cost just a penny back then!

As history would show, the various styles of women’s loafers likely evolved from the popularity of a similar shoe: the Oxford.


The Rise In Popularity

As stated by Nancy Macdonell in her article about what she calls “fashion’s favorite flat” Nancy described loafers as “the footwear of choice for off-duty MBAs” adding “loafers have a distinct lack of obvious fabulousness.”

Seems a bit harsh for an innocent style of shoe that has stood the test of time, does it not? Well, maybe not. Perhaps it’s just those characteristics that make the loafer the beloved footwear that it is. But even Jean Touitou, the founder of A.P.C. claims that loafers are one of the most difficult shoes to get right. But yet so many people continue to include loafers as vital pieces of their eclectic wardrobes. They’re no longer only for those sporting the logos of Tod’s or Ralph Lauren. Whether you’re one to follow trends or go your own way in regards to fashion choices, loafers seem to be one outfit staple that has stood the test of time.

Fortunately, you can easily find a pair that suits your personal style, thanks to the variety of loafers available. But when shopping, would you really know what to look for? Not to worry, we’ve got the guide to help you through the shopping process, complete with inspiration for how to style the popular and comfortable shoe.


Shopping For Loafers


Loafers aren’t and never have been a “sexy” shoe. Shoes more commonly recognized as sexy, such as high heels, tend to be popular both for business-appropriate styles and “girls-night-out” outfits. However, loafers seem to be rising in popular among both those parties, as well as those looking for a comfortable show to pair with just about any outfit, if put together correctly.

When browsing for the right pair of loafers, you may notice that you’ll be forced to choose from pilgrim-inspired styles, platform loafers made from suede, hand-crafted leather loafers, and so much more. Fortunately, the price range varies just about as much as the styles, so no matter your budget, there’s a good chance you can find the right pair for you. Remember, you don’t have to settle. So keep an eye out until you find the perfect pair, or three, for you.


How To Style Women’s Loafers

This is where things can get a little tricky. Unlike other shoes, loafers are a little “picky” if you will. The key to styling the shoes correctly is more about picking the right outfit and then finishing it off with your favorite pair of loafers. With that being said, let’s go through the different ways you can style loafers.


Simple Street Style

Perhaps the easiest way to style loafers is by paring them with your favorite street-style outfit. Go ahead and channel your inner James Dean for this style. Don’t know who James Dean is? Think retro rock ‘n roll style. Pull on your favorite pair of dark-colored skinny jeans, slip into a simple white t-shirt, pair it with a leather jacket, and finish the outfit with a pair of patent loafers. Seems simple enough right? Not to mention comfortable!

For a more edgy street-style way to wear loafers, swap out the jeans for patent leggings and instead of a t-shirt and jacket, pull on a patterned yet simple tee with a statement coat.


Office-Friendly Style

r a more office-friendly way to wear your favorite pair of loafers, it’s important to stick to the dress code. That being said, you can still flaunt your personal style and dare to be bold. A great way to accommodate a stylish pair of loafers is with a knee-length skirt. Pair the skirt with a crew-neck sweater and loafers to match and you’ve got a complete outfit ready to wow!

You could also pair a black skirt with a simple top or blouse and then add a bold coat before finishing the outfit with patent loafers. If you’re dealing with colder weather try wearing loafers with a skirt and black tights or pantyhose. You could even slide on your favorite pair of loafers to wear with a long pleated skirt. Pair the skit with a relaxed top for a balanced silhouette and you’re good to go.


Preppy Style

If you have khaki pants ora khaki skirt, you can pair it with a blazer and a button down shirt. Think about the sorts of outfits you would see at a country club or a polo match. There’s bound to be a ton of loafers on the feet walking around those events! A preppy outfit is a great way to bring out your inner tomboy while dressing comfortably and fashionably. Another great preppy way to wear loafers is with a belted shirt dress. You can finish off the entire outfit with an oversized hat.


Bold Style

For a super bold look, don’t be afraid to think outside of the box. You can go bold by wearing black from head to toe. Or you can find a pair of super-wide leg pants and pair them with animal print loafers. You could also put on your favorite pair of cotton joggers and an oversized tee for more of a dressed down look. Your style is what you make of it, so if you think you look great, go for it!


How to Wear Women’s Loafers:Socks Or No Socks?

Socks or not seems to be a big debate among those who wear loafers, those who style them, and those who have a general interest in fashion. The majority of people tend to side with wearing loafers without socks, but there do seem to be a few acceptable exceptions. For example, although they aren’t exactly socks, it’s perfectly fine if you want to wear a pair of black tights or panty-hose with your loafers. Trust me, you won’t get any sideways glances with that pairing.

Otherwise, if you’re determined to wear socks stick to two rules. First, only wear socks if you’re wearing pants. That way, the socks don’t stand out like a sore thumb. Second, wear no-show socks that are meant to cut low on the ankle and avoid being seen. That way you can enjoy the comfort of socks without risking a possible fashion faux-pas.


In Conclusion

It’s clear by now that loafers are a style of shoe that are going to be around for a long time. If they’ve lasted the last 100 years, it’s safe to say they’ll last 100 more. If you haven’t yet invested your time and money into finding a great pair, now is the perfect time. Be sure to pay attention to how you feel when you slide them on because that’s what matters more than anything else. Once you find the perfect pair of loafers for you, venture out and try different ways to pair them clothes you already have. You truly can’t go wrong if you follow the simple rules of fashion. Although, rules are made to be broken, right? So you do you. Go out there and start a trend. Be bold, be confident, and rock those loafers.