Penny Loafers

Penny loafers are not only one of the classy and versatile types of loafers out there; they have some fun history to their name. These shoes sprung into existence in the 1950s, when prep students were known for keeping small coins in the diamond-shaped slot on top of the shoe. Penny loafers have since then become a fashion legend and staple footwear in the elegant men's wardrobe.  

A quick way to identify a penny loafer for men, amongst other types of loafers, is the strap attached across the top, which, also, is a slot that houses the small penny that made it ubiquitous. Penny loafers are available in a range of materials like suede and leather and colors like black, brown, tan, white, burgundy, etc. They're comfortable, classic, and versatile, making them downright elegant shoes for stylish gents.  

There are many classy men’s shoes out there, but only a few are as stylish as the classic penny loafers. They’re a footwear staple, and every smart gent should have at least a pair of them. Well, I guess you already did that. Isn’t it? So, here’s the time to learn how to wear penny loafers like a dapper man.  

As far as it goes, having a pair of classy footwear won’t magically make you look chic if you’ve got the wrong combination. So, the matching process is probably more essential than anything else. Don’t worry if it’s your first time, though. We’re here to guide you on how to wear penny loafers without looking trashy.  

Generally, pairing loafers with jeans is like placing five and six together—they're just a perfect match. You probably have been rocking your jeans with sneakers and flat shoes, but here’s time to switch things up and set yourself in a more fashionable, dressier way.  

The number one rule of thumb for wearing penny loafers with jeans is to ensure the length of the jeans is perfect. Baggy jeans just don't work well with loafers unless you want to look trashy. And when complementing your jeans with loafers, choose contrasting colors for a better look. Pair brown loafers with blue jeans and ensure your shirt matches as well. Do you get it? Nice.  

Ok, you're not stuck with denim; your classic penny loafers can also make a statement with chinos. When you're ready to project a smart-casual look, wearing your loafers with chinos can be the safest, adoring option available. Depending on how you want it to look, you can opt for a pair of blue chinos with brown penny loafers, then throw in your favorite shirt. And if you wish, you can add a blazer.  

Chinos fill that gap of matching your favorite pants and footwear without leaving a doubt. And mind you, colored, bright chinos are always attractive and even more attractive when you pair them with a contrasting pair of loafers. Black loafers often match bright-colored chinos like tan, cream, white, and others. Meanwhile, if you want to go the extra mile, you can opt for a pair of white loafers with white chinos and a pale blue denim jacket.  

So, what’s next after wearing your favorite pant with a shirt and a pair of elegant penny loafers? You throw on a blazer! Blazers and penny loafers are superb when you pair them with jeans, chinos, or trousers. Just ensure you have the right color combo, and you need nothing to worry about anymore. Also, remember to keep your shirt tailored to elevate the dressiness.  

Yes, you can also wear your penny loafers with shorts. And that reminds us you can look good without wearing those long, long pants. When you think of a nice pair of outfits to rock your summer look, you can’t go wrong with wearing loafers and shorts.  

Shorts are probably not the most stylish outfit there and might look preppy on some people. But you can always go for it if you want it. Just make sure you wear tailored shorts, with hems stopping a little above your knees. Shorts and loafers look great when paired with a tailored, tucked-in shirt and a belt. And please, go sockless to avoid looking like a primary school student. It’s as simple as that  

Not just your casual jeans, chinos, or any other regular pant; penny loafers look good with suits as well. Although they might not be a recommended outfit match for job interviews or business proposals, you can still wear penny loafers with your suits if you are aiming for a casual or smart casual look.  

Just ensure to go with tailored suits, with the length of your trousers hitting a little above your ankle (I mean, not too long). And of course, you can throw in a tie if needed. Just ensure everything is color-coded to avoid looking shabby. Your biggest fear might be if it's right to wear loafers sockless or with socks. Yes, that has been one of the hottest questions recently, and all you need to know is that it’s up to you. It’s something of personal preference.  

The straight answer is loafers look good without socks. But if you must, we won't beat you for wearing them with socks. Jokes apart, wearing loafers without socks has been trending for a while now, and according to what we see, it’s by far the cleanest combination. Well, that’s if done well. If you’re forgoing socks with your loafers, opt for fitted pants with a moderate length to elevate your look.  

And while no rule binds you from wearing socks with loafers, be careful when you do so. Ensure your socks are in line with your outfit. Just go for what works for you. And that pretty much sums up how to wear penny loafers without looking trashy. As you can see, they’re versatile, and easy to style, and you should have at least a pair in your wardrobe.