Penny loafers are classic, versatile shoes that can easily be dressed up or down. Pairing loafers with shorts is a timeless preppy look that exudes laid-back sophistication. If you’re wondering if you can pull off penny loafers with shorts and want tips on how to do it stylishly, you’ve come to the right place.

Here’s a quick answer: Penny loafers look great with shorts when you stick to a preppy aesthetic. Focus on tailored shorts in khaki, white, navy or seersucker. Pair with loafers in brown leather or suede. Add socks in the summer or go sockless.

Finish the look with a polo, linen button-down or Breton top.

The History of Penny Loafers

Penny loafers, a classic shoe style beloved by both men and women, have a rich history that dates back several decades. Understanding the origins and evolution of this timeless footwear can provide valuable insights into how to wear them with shorts.

Origins at Ivy League Universities

The penny loafer’s story begins at Ivy League universities in the early 20th century. Students at schools like Harvard and Princeton sought a comfortable and versatile shoe that could be worn both casually and in more formal settings.

This led to the creation of a slip-on loafer style with a distinctive strap across the vamp.

Initially, these loafers were made with a simple design and lacked the iconic penny slot. However, as the popularity of the style grew, students began inserting a penny into the slot as a decorative touch. This small detail would go on to become a defining characteristic of penny loafers.

How the Penny Loafer Got Its Name

The exact origins of the name “penny loafer” are somewhat disputed. One popular theory suggests that the name originated from the practice of placing a penny in the slot, as mentioned earlier. Students would use the penny to make emergency phone calls, ensuring they always had a coin readily available.

Another theory suggests that the name came from the similarity between the shape of the strap and the coin. The strap, when viewed from the side, resembles the profile of a penny, hence the name “penny loafer.”

Popularity Explosion in the 1950s and 1960s

The penny loafer experienced a surge in popularity during the 1950s and 1960s. This was largely due to the influential style icons of the time, such as James Dean and Elvis Presley, who frequently wore penny loafers in their films and public appearances.

The shoe’s versatility and timeless appeal made it a staple in both casual and formal settings, further cementing its status as a fashion must-have. Today, penny loafers continue to be a popular choice for those seeking a classic and sophisticated look.

For more information on the history of penny loafers, you can visit Gentleman’s Gazette.

What to Look for When Buying Penny Loafers

Leather Types: Calfskin, Cordovan or Suede

When purchasing penny loafers, it’s important to consider the type of leather used in their construction. The most common leather types for penny loafers are calfskin, cordovan, and suede. Calfskin is a popular choice due to its durability and flexibility.

Cordovan, on the other hand, is known for its high-quality and glossy finish. Suede penny loafers can add a touch of sophistication to your outfit and are perfect for more casual occasions. It’s essential to choose a leather type that aligns with your personal style and the occasion you plan to wear them for.

Color: Brown, Tan, Burgundy or Black

When it comes to color, penny loafers are available in a variety of options, but some classic choices include brown, tan, burgundy, and black. Brown penny loafers are versatile and can be paired with a wide range of outfits, making them a popular choice for many.

Tan penny loafers offer a lighter and more casual look, perfect for summer months. Burgundy penny loafers add a touch of sophistication and can elevate any outfit. Black penny loafers, on the other hand, are a timeless and versatile choice that can be dressed up or down.

Consider your wardrobe and personal style when selecting the color of your penny loafers.

Other Design Details to Consider

Aside from leather type and color, there are other design details to consider when buying penny loafers. Pay attention to the stitching and craftsmanship, ensuring that the loafers are well-made and will last. Look for a comfortable and cushioned insole to ensure all-day comfort.

Some penny loafers come with tassels or other embellishments, adding a touch of personality to the shoes. It’s important to try on the loafers and walk around in them to ensure a proper fit and comfort level.

Additionally, consider the sole of the loafers – rubber soles provide better traction and durability compared to leather soles.

Matching Penny Loafers With Shorts

When it comes to pairing penny loafers with shorts, there are a few key factors to consider. The right combination can create a stylish and polished look, while the wrong pairing can leave you looking mismatched.

In this comprehensive guide, we will explore different ways to match penny loafers with shorts to help you achieve a fashion-forward outfit.

The Preppy Look: Khaki or Seersucker Shorts

For those aiming for a preppy look, khaki or seersucker shorts are an excellent choice to pair with penny loafers. These classic shorts provide a clean and sophisticated canvas for your loafers to shine.

The neutral tones of khaki or the timeless charm of seersucker create a harmonious balance when paired with the elegance of penny loafers.

When styling this combination, consider adding a crisp button-down shirt or a lightweight sweater for a polished finish. This ensemble is perfect for summer parties, garden gatherings, or even a casual day at the office.

Going Casual: Denim or Chino Shorts

If you prefer a more casual look, denim or chino shorts are the way to go. While still maintaining a sense of sophistication, these shorts offer a laid-back and effortless vibe. Pairing penny loafers with denim or chino shorts is a great choice for weekend outings, picnics, or casual social events.

When styling this combination, opt for a relaxed t-shirt or a casual button-down. Consider rolling up the cuffs of your shorts for an added touch of style. Don’t be afraid to experiment with different colors and patterns to inject some personality into your outfit.

Acceptable Shorts Lengths

When it comes to the length of your shorts, it’s essential to find a balance that flatters your body type and suits the occasion. For a classic and timeless look, opt for shorts that hit just above the knee. This length is universally flattering and appropriate for most settings.

However, if you’re feeling a bit more adventurous, you can experiment with shorter or longer lengths depending on your personal style and comfort level. Just be mindful of the occasion and ensure that your shorts are not too revealing or overly conservative.

Tailoring for a Polished Look

To elevate your outfit and achieve a truly polished look, consider having your shorts tailored. Properly fitted shorts can make a significant difference in your overall appearance, creating a sleek and put-together aesthetic.

When it comes to tailoring shorts, focus on achieving a proper fit around the waist and hips. Avoid shorts that are too tight or too loose, as they can throw off the balance of your outfit. Taking the extra step to have your shorts tailored will ensure that they complement your penny loafers perfectly.

Remember, fashion is about expressing yourself and having fun with your style. While these guidelines can serve as a starting point, don’t be afraid to experiment and find what works best for you. So go ahead, confidently sport your penny loafers with shorts and embrace your own unique fashion statement!

Socks or No Socks?

When it comes to wearing penny loafers with shorts, one of the most debated topics is whether to wear socks or go sockless. Both options can create a stylish and fashionable look, but it ultimately depends on personal preference and the occasion.

The Summer Sockless Look

Going sockless with penny loafers and shorts is a popular choice during the summer months. It gives off a casual and effortlessly cool vibe, perfect for days spent by the beach or exploring the city. This look is often associated with a more laid-back and relaxed style.

However, it’s important to note that going sockless requires proper foot hygiene to avoid any unpleasant odors. Make sure to wash and dry your feet thoroughly before slipping on your loafers. You can also consider using foot powder or antiperspirant spray to keep your feet dry and fresh.

When to Wear Socks With Penny Loafers and Shorts

While going sockless is a popular choice, there are occasions and situations where wearing socks with penny loafers and shorts is more appropriate. For formal or semi-formal events, it’s generally recommended to wear socks to maintain a polished and put-together look.

If you choose to wear socks, opt for low-cut or no-show socks that won’t be visible when you’re wearing your loafers. This will help create a seamless and clean look. Consider matching the color of your socks to your shorts or loafers for a coordinated and stylish outfit.

Sock Style and Length Considerations

When it comes to selecting the right socks for your penny loafers and shorts, consider the style and length of the socks. Ankle-length socks are a versatile choice that works well with most shorts. They provide a bit of coverage without being too visible.

If you want to make a statement or add a pop of color to your outfit, you can opt for patterned or brightly colored socks. Just make sure the patterns or colors complement the rest of your ensemble for a cohesive look.

Remember, the key is to experiment and have fun with your style. Whether you choose to go sockless or wear socks with your penny loafers and shorts, confidence is key in pulling off the look. So go ahead and rock your favorite pair of loafers with your shorts, and let your personal style shine!

Tops to Pair With Penny Loafers and Shorts

When it comes to wearing penny loafers with shorts, choosing the right top is essential to create a stylish and well-put-together look. Here are some top options that you can consider:

Polo Shirts

Polo shirts are a classic choice that pairs perfectly with penny loafers and shorts. The casual yet polished look of a polo shirt complements the laid-back vibe of shorts, while the collar adds a touch of sophistication. Opt for solid colors or subtle prints to keep the focus on your loafers.

If you want to add some personality, you can experiment with bold or contrasting colors.

Oxford Button-Down Shirts

An oxford button-down shirt is another great option to wear with penny loafers and shorts. This timeless combination exudes a preppy and refined look. Choose a crisp white or light blue shirt for a clean and classic appearance.

For a more relaxed vibe, you can roll up the sleeves and leave a few buttons undone.

Breton Stripes and Knits

For a nautical-inspired look, consider pairing your penny loafers and shorts with a Breton striped shirt or a lightweight knit. The horizontal stripes add a touch of playfulness, while the loafers keep the outfit looking polished.

Opt for a navy and white striped shirt for a timeless and versatile option.

Blazers or Sweaters (For Cooler Weather)

When the weather gets cooler, you can elevate your penny loafers and shorts ensemble by adding a blazer or a sweater. A tailored blazer instantly adds a sophisticated touch to your outfit, making it suitable for dressier occasions.

Alternatively, you can opt for a lightweight sweater in a complementary color to keep you warm without sacrificing style.

Remember, the key to successfully pairing tops with penny loafers and shorts is to strike a balance between casual and refined. Experiment with different combinations to find your personal style and create looks that make you feel confident and comfortable.

Accessories and Final Touches

Belts: Match Leather Color to Shoes

When it comes to accessorizing your penny loafers with shorts, a belt is a must-have item. Not only does it add a polished and put-together look to your outfit, but it also serves a practical purpose of keeping your shorts in place.

To create a cohesive and stylish look, it is essential to match the color of your belt to your penny loafers. This creates a harmonious and well-coordinated appearance that will elevate your overall outfit.

If you have brown penny loafers, opt for a brown leather belt, and if you have black penny loafers, choose a black leather belt. This simple matching technique will make a significant difference in your outfit’s overall aesthetic.

Ties: Bow Tie or Knit Tie for Interest

While ties may not be a traditional accessory to wear with shorts, they can add a touch of interest and personality to your outfit. When it comes to choosing a tie to wear with your penny loafers and shorts, there are a few options that work particularly well.

One option is a bow tie, which adds a dapper and playful element to your attire. Another option is a knit tie, which provides texture and adds a casual yet stylish vibe. Both options can be paired with a button-down shirt and shorts to create a unique and fashionable look.

Remember to choose a tie that complements the colors of your outfit and adds a pop of visual interest.

Hats: Baseball Cap or Straw Boater

Adding a hat to your penny loafers and shorts ensemble can instantly elevate your look and provide protection from the sun. Two popular hat options that pair well with this outfit combination are the baseball cap and the straw boater.

A baseball cap adds a sporty and casual touch, perfect for a laid-back summer day. On the other hand, a straw boater hat exudes a more sophisticated and vintage-inspired aesthetic, ideal for a dressier occasion.

Whichever hat you choose, make sure it complements your overall outfit and reflects your personal style.

Sunglasses: Aviators or Wayfarers

No summer outfit is complete without a stylish pair of sunglasses. When it comes to pairing sunglasses with penny loafers and shorts, two classic styles stand out: aviators and wayfarers. Aviators have a timeless appeal and offer a sleek and sophisticated look.

They work well with a range of face shapes and outfit styles. Wayfarers, on the other hand, have a retro and cool vibe, adding a touch of nostalgia to your overall appearance. Whether you opt for aviators or wayfarers, make sure to choose a frame shape and color that complements your face shape and enhances your outfit’s overall aesthetic.


Penny loafers are a versatile classic shoe that looks smart with shorts when styled appropriately. Stick to a tailored preppy aesthetic in warm weather colors like khaki and navy. Consider the formality of the shorts and top when deciding on socks or no socks.

Add classic accessories like sunglasses, baseball caps or bow ties to finish the sophisticated penny loafer and shorts outfit.

Similar Posts