What Are Penny Loafers? How to Wear, Style, and Choose the Right Color

Penny loafers are a very recognizable kind of shoes thanks to their unique penny design. People love these shoes for formal wear and many also like penny loafers for casual use. But many people don’t know how to wear penny loafers outside of formal situations, or if they even should do it, because they give a formal feeling. Are these just for formal wear?

What intrigues some people more is the question: “Why is it called penny loafers?” They assume penny loafers have probably something to do with pennies or cents. But is that the case?

Others feel unsure about the color of penny loafers they should get. Some want shoes that work well with formal wear, others want casual, and some are looking for a color that can accommodate both formalities. These fashion-aware people are constantly thinking about how to style loafers so they don’t look off-fashion.

If you also happen to have some of these questions, then continue reading because this guide will give you all the answers and make everything clear.

What are Penny Loafers?

Penny loafers are defined as “slip-on shoes with a simple design and a leather strap across the top.” There are so many different yet similar-looking shoes that they can leave most people confused. But a penny loafer is uniquely, simply recognizable. You can instantly recognize one of these whenever you see one, even if they’re sitting among their loafer look-alikes, like tassel loafers and bit loafers.

Penny loafers have a simple strap on top with an even simpler cut-out in its middle, which is what actually distinguishes them from the rest of the loafers.

In usual cases, penny loafers have the following appearance qualities:

• A low heel

• No laces

• A clean and rounded or slightly pointed toe

• A leather or rubber sole

• A structured shape

Remember these qualities to better recognize different kinds of penny loafers.

Why Are They Called Penny Loafers?

Penny loafers have a very interesting history. 

In the mid-20th century, students in the United States started to place a penny into the slit of the leather strap on their loafers.

Why? Because back then, public payphones were common which people used to make calls outside of homes. And payphones in many parts of the U.S. cost two cents at that time. Placing a penny into each shoe’s leather strap (which could accommodate exactly one penny) became a practical way to always have two pennies for an emergency call.

The practice caught on and people started calling these shoes “penny loafers” because of the widespread practice. And that’s why penny loafers are called penny loafers today. They certainly do have to do with pennies, though that’s not what they’re worth in any way.

What Are Penny Loafers Made Of?

The most common material shoemakers use to make penny loafers is leather. Different kinds of leather are used to make penny loafers of different comfort levels, formalities, appearance, feel, and durability. This makes the material an important factor to consider when you buy shoes since it influences almost everything there is to them (more on this later). Some common materials include:

• Smooth Leather: There are smooth leather penny loafers that are strong and hold their shape well while developing a patina over time. These are common in offices because they’re used for formal wear.

• Suede Leather: Then there are suede penny loafers. These have a soft surface with a relaxed feel. You can’t help but feel that these aren’t the office kind, because they’re casual in appearance.

• Synthetic Material: Penny loafers are also made from synthetic material (man-made materials). These are also designed to look like leather—some even mistakenly think they’re leather-made. These shoes are affordable but not the best in quality.

How to Wear Penny Loafers

Penny loafers aren’t too picky. You can wear them as you like, but there are some considerations to make.

If you’re thinking of the shoe’s fit, they should fit snugly without feeling neither too tight nor loose. A loose penny loafer will likely slip at your heel because they don’t have laces to tighten them up. Leather penny loafers also soften and become slightly more loose over time, so make sure you get the ones that feel snug and not loose at the time of purchase.

But if you’re thinking whether you should wear socks with your penny loafers, then the short answer is that it’s your choice as long as the setting is casual. Formal occasions always require socks. Here’s what’s acceptable:

When it comes to wearing socks with penny loafers, wear them with:

• Dress socks for formal or office wear

• No-show socks for a clean and modern look

• Barefoot-style in warm weather, but using no-show socks is recommended for hygiene

Not wearing socks can lead to some hygiene and comfort issues like sweating, slippery shoes from the inside due to sweat, odors, and blisters on your skin due to the shoe’s material constant rubbing.

How to Style Penny Loafers

Penny loafers offer you versatility. Their formality ranges from casual to business casual and formal. But they’re not ultra formal like the ones for black-tie events or strict business professional settings. These shoes always give a slightly more relaxed and casual feeling than those truly formal Oxford and the likes. But that’s about it.

Let’s see how to style penny loafers:

Occasions and Events

You can style penny loafers for the following types of occasions:

• Formal and Semi-Formal: Semi-formal wedding events (like Walima), dinner parties, evening events, and formal events like Walima when paired with a suit.

• Exceptions: Grooms are exempted from these rules because they usually wear either formal footwear on Walimas or traditional khussas on Baraats.

• Business and Professional Settings: Job interviews, usual office days, and when you want to wear business casual attire. 

• Exceptions: If your office leans on formal dressing then avoid the "no-socks" look and wear matching socks to maintain professional decorum. Also, stick to more formal footwear for more formal occasions like high-finance or legal interviews.

• Casual Occasions: Weekend errands, outings, brunches, summer events, and travel.

• Exceptions: Consider the monsoon season an exception to protect your high-quality suede penny loafers. These are sensitive shoes which can get permanent damage from water and street mud. Plus, avoid these shoes on solemn occasions like a funeral prayer as they signal style and fashion more than simplicity.

Clothing and Wardrobe

Pair your penny loafers with the right kind of outfit based on their color:

1. Formal and Semi-Formal Penny Loafers

Dark-colored penny loafers are used for these kind of occasions, including:

• Black Color with Polished Leather

• Outfits: A charcoal or navy three-piece suit, or a black or dark grey prince coat with fitted trousers. A starched white shalwar kameez set with a black structured waistcoat also works.

• Style Notes: Maintain shine and keep the outfit sharp and the shoes polished. Don’t wear socks at all or go for black no-show socks for maintaining a cleaner break.

• Oxblood Leather

• Outfits: A slightly less formal dark brown suit. You can also wear a beige or tan waistcoat over a white kurta pajama for a warmer contrast.

• Style Notes: This color adds depth which makes it a great alternative to black for winter events. Make sure the shoes are still polished to a high sheen.

2. Business and Professional Settings

These occasions suit slightly light-colored loafers, including:

• Brown or Tan Leather

• Outfits: Navy blue or grey wool trousers with a crisp light blue or white dress shirt; a classic plain shalwar kameez set in white, off-white, or light blue, worn with a brown leather belt that matches the shoes.

• Style Notes: Brown leather offers versatility and is the backbone of the business-casual. Make sure the shoes are unscuffed and well-maintained.

• Suede (Dark Navy or Brown)

• Outfits: Chinos in olive green or khaki with a button-down shirt or a more relaxed-fitting kurta with a simple waistcoat for modern offices.

• Style Notes: Suede is softer and conveys a more modern, approachable professional look. It pairs well with earthy tones common in Pakistani workwear.

3. Casual Occasions

Casual occasions require the lightest colors. Light brown penny loafers, especially white sole loafers, make for the perfect casual shoes.

• Tan or Light Brown Suede

• Outfits: Slim-fit blue/black jeans with a casual polo or T-shirt, light cotton shalwar kameez to give a relaxed look for the weekend, or shorts for summer travel.

• Style Notes: Lighter tones suede is fully casual. You can go completely sockless if you want to maximize your comfort as well as the shoes’ breathability during summer heat.

• Textured or Colored Leather (e.g., woven, white, or blue)

• Outfits: Kurtas in bright colors like yellow/green for Mehndi events. Pair them with white pajamas or linen trousers.

• Style Notes: Use these for events where you want to add personality. They work best as the standout piece of the outfit paired with neutral clothes elsewhere.

You can style penny loafers in many ways depending on the occasion and your style.

And don’t worry if you’re not a very fashion-oriented person and feel unsure about how to style your penny loafers. You can ask a friend or someone more knowledgeable for advice. But you can trust your instincts as well. If your penny loafers seem to clash with your outfit and make it feel “off,” they probably do.

How to Style Black Penny Loafers

Black penny loafers look like formal shoes compared to other color kinds. These are best with formal outfits like:

• Black, grey, or dark navy trousers

• Office wear

• Evening or professional settings

Don’t wear them for casual outfits like blue jeans or your usual summer clothing will look off. Avoid such overly relaxed outfits. Otherwise, simpler clothing and darker colors can help make them feel intentional rather than forced.

What Color Penny Loafers Should I Get?

This boils down to the purpose of your wear. Consider the occasions where you will wear them. The general rule is that you should get darker colors for formal, brown/dark brown for a wider range of occasions, and lighter for casual.

• Black for formal wear

• Dark brown for both formal and casual

• Tan/Light brown for casual summer wear

If you want to be able to switch between casual and formal then go for dark brown.

Conclusion

Penny loafers are a type of slip-on loafer shoes with a simple design and a leather strap across the top. They’re called penny loafers because of a historical practice in the United States in the mid 20th century when people, primarily students, started keeping a penny in each shoe’s leather strap through the slit to keep emergency change for public payphones.

From a fashion point of view, penny loafers are versatile shoes that you can wear on plenty of occasions from formal to semi formal, business casual to professional settings, and casual. They pair well with a variety of outfits depending on their color.