Summer sale for all Bubbles Suits - off 50%! Shop Now

How To Style Penny Loafers

How To Style Penny Loafers


How To Style Penny Loafers: Penny loafers, the iconic slip-on shoes with a distinctive strap across the front and a diamond-shaped cutout, have stood the test of time as a symbol of classic footwear elegance. Originally popularized on college campuses in the mid-20th century, these versatile loafers have transcended generations and fashion eras, earning a place in the closets of both men and women around the world.

In this comprehensive guide, we’ll explore the art of styling penny loafers to help you unlock their timeless charm and versatility. Whether you’re a seasoned fashion aficionado or someone looking to add a touch of sophistication to your everyday attire, penny loafers can be your reliable and stylish companions.

From choosing the perfect pair to match your personal style and occasion to understanding how to pair them with various outfits, we’ll cover all the essentials. Penny loafers can effortlessly transition from formal to casual settings, making them a valuable addition to your wardrobe. Whether you’re aiming for a sharp, professional look, a smart-casual ensemble, or a laid-back weekend outfit, we’ve got you covered.

Additionally, we’ll explore the importance of proper care and maintenance to keep your penny loafers looking great for years to come. The world of penny loafers and discover the endless possibilities they offer for crafting timeless and elegant looks.

How To Style Penny Loafers

What goes well with penny loafers?

For casual occasions, you can pair penny loafers with jeans, chinos, shorts, and a casual shirt or t-shirt. This look is perfect for a weekend brunch or a casual evening out. For a more formal occasion, penny loafers can be paired with dress pants, a blazer or a suit, and a dress shirt.

Penny loafers are a versatile and timeless footwear choice that pairs well with a range of outfits. Here’s what goes well with penny loafers:

Casual Wear: Penny loafers are a perfect match for casual outfits. They look great with well-fitted jeans, whether in classic blue or a darker wash. Pair them with a t-shirt, polo shirt, or casual button-down for a relaxed, everyday look.

Business Casual: Penny loafers can be dressed up for business-casual attire. Wear them with dress slacks or chinos in a coordinating color. Add a dress shirt or a lightweight sweater and, if needed, a blazer to complete the ensemble.

Suits: While not as formal as oxfords, penny loafers can be worn with suits, especially in more relaxed or creative work environments. Stick to lighter-colored suits and consider going sockless or wearing no-show socks for a modern touch.

Shorts: During the warmer months, penny loafers can be worn with shorts. Choose tailored shorts with a slightly above-the-knee length and pair them with a casual shirt for a stylish summer look.

Accessories: Don’t forget to coordinate your belt with the color of your penny loafers for a polished appearance. Adding sunglasses, a watch, or a stylish pocket square can enhance your overall outfit.

What pants to wear with penny loafers?

Wearing Penny loafers with jeans ensure a smooth look. Look into the right fit for jeans with straight and slim-cut and avoid baggy, wide-legged, and excessively tight jeans. The next thing is to coordinate the color of the jeans. Navy loafers can work with medium washed, indigo, grey or white jeans.

Penny loafers are a versatile footwear choice that can be paired with a variety of pants to create stylish outfits. Here’s a breakdown of the types of pants that go well with penny loafers:

Dress Slacks: Penny loafers can be worn with dress slacks for a smart and sophisticated look. Opt for wool or cotton slacks in classic colors like navy, gray, or charcoal. This combination is ideal for business-casual and semi-formal settings.

Chinos: Chinos are a perfect match for penny loafers, creating a versatile and comfortable outfit. Choose slim or tailored chinos in colors such as khaki, beige, olive, or navy. This combination is great for both casual and business-casual occasions.

Jeans: Penny loafers can be dressed down with jeans for a stylish yet relaxed look. Dark wash or black jeans work well for a slightly dressier appearance, while lighter wash jeans offer a more casual vibe. Ensure the jeans have a slim or straight leg cut for a polished look.

Corduroy Pants: Corduroy pants in rich, seasonal colors like burgundy, forest green, or brown can pair beautifully with penny loafers during the colder months. This combination offers a touch of texture and warmth.

Shorts (Seasonal): In the summer, penny loafers can be worn with tailored shorts for a preppy and comfortable look. Stick to shorts with a slightly above-the-knee length in classic colors.

Linen or Cotton Trousers (Summer): Lightweight linen or cotton trousers in light colors are great for warm weather and complement penny loafers for a cool and breathable ensemble.

Are penny loafers stylish?

Penny loafers strike that retro-yet-timeless vibe that looks so good on guys. Plus, these shoes are quite literally effortless (slip on! no laces!), and you can dress them up or down. Really, there isn’t any good reason not to add a pair of penny loafers to your shoe collection.

Yes, penny loafers are undeniably stylish and have maintained their popularity in the world of fashion for decades. Here are several reasons why penny loafers are considered stylish:

Timeless Design: Penny loafers feature a classic and minimalist design that transcends trends and seasons. Their simple yet elegant silhouette appeals to individuals with diverse fashion tastes.

Versatility: Penny loafers are incredibly versatile. They can be dressed up or down, making them suitable for various occasions, from casual outings to more formal events. They pair well with a wide range of outfits, from jeans and chinos to suits and shorts.

Comfort: Their slip-on style and comfortable fit contribute to their enduring appeal. They provide comfort without sacrificing style, making them a practical choice for everyday wear.

Quality Materials: High-quality penny loafers are typically crafted from premium materials like leather or suede, ensuring durability and a polished appearance.

Iconic Brands: Many renowned footwear brands produce penny loafers, offering a wide range of styles, colors, and materials. This allows individuals to find a pair that suits their unique style preferences.

Classic Associations: Penny loafers have a storied history and are associated with the Ivy League and preppy fashion, adding a touch of sophistication to any outfit.

Do you wear socks with penny loafers?

Most people will tell you that wearing loafers means no socks. Frankly, both looks (socks or sans sock) work, it’s just a matter of how you do it. When going “sockless”, we suggest no-show socks. They are the easiest way to protect your shoes and avoid sweaty feet.

The choice of whether to wear socks with penny loafers depends on your personal style, the season, and the specific look you’re aiming to achieve.

Sockless Look: Going sockless with penny loafers is a classic and popular choice, especially during the warmer months. It creates a clean and relaxed appearance, allowing the loafers to shine. However, going sockless can sometimes lead to moisture and odor concerns.

No-Show Socks: To maintain comfort, hygiene, and a sockless appearance, you can opt for no-show or low-cut socks. These are designed to remain hidden beneath the shoe’s collar, giving the illusion of socklessness while providing some moisture-wicking benefits.

Dress Socks: In more formal or cooler settings, wearing traditional dress socks with penny loafers is perfectly acceptable. Choose socks that match the formality of your outfit and coordinate with your trousers or suit.

Statement Socks: Some individuals choose to make a fashion statement by wearing colorful or patterned socks with their penny loafers. This adds a pop of personality to the outfit and can work well in casual or creative settings.

How To Style Penny Loafers

What are the key features that distinguish penny loafers in terms of style?

Penny loafers are a classic and timeless footwear style known for several key features that distinguish them in terms of style:

Strap Across the Front: The most distinctive feature of penny loafers is the leather strap that runs horizontally across the vamp (the front part of the shoe). This strap is often adorned with a diamond-shaped cutout, giving the shoes their signature look.

Slip-On Design: Penny loafers are slip-on shoes, lacking laces or buckles. This slip-on feature adds to their convenience and casual elegance.

Low Heel: Penny loafers typically have a low, flat heel or a slight heel, making them comfortable for all-day wear.

Moc Toe Stitching: Many penny loafers feature moccasin-style stitching around the toe box, adding to their casual and laid-back appeal.

Versatile Colors: Penny loafers come in a range of colors, with brown and black being the most common. These versatile color options make it easy to match them with various outfits.

Timeless Design: One of the most enduring aspects of penny loafers is their timeless design. They have remained a fashion staple for decades, suitable for both formal and casual occasions.

Penny Slot: The small cutout, often referred to as the “penny slot,” is where the name of these loafers comes from. It was traditionally used to hold a coin, such as a penny, hence the name “penny loafers.”

How can I style penny loafers for a formal, business-appropriate look?

Styling penny loafers for a formal, business-appropriate look can be both sophisticated and comfortable. Here’s how to achieve this polished appearance:

1. Choose High-Quality Penny Loafers: Opt for a pair of well-crafted penny loafers made from high-quality leather. Classic colors like black or dark brown are ideal for formal settings.

2. Select Tailored Trousers: Pair your penny loafers with well-tailored dress trousers. Ensure they have a clean, straight leg and minimal break at the bottom to create a sharp, streamlined look.

3. Crisp Dress Shirt: Wear a well-fitted, button-down dress shirt in a solid color or subtle pattern. Tuck it in neatly for a polished appearance.

4. Add a Suit Jacket: Incorporate a well-fitting suit jacket or blazer that complements your trousers. This combination instantly elevates the formality of the outfit.

5. Accessories: Complete the look with a silk tie and a leather belt that matches the color of your penny loafers. Consider adding a pocket square for a touch of sophistication.

6. Grooming Matters: Pay attention to personal grooming, including a clean shave or well-kept facial hair, and neatly styled hair.

7. Socks: Choose over-the-calf dress socks that match the color of your trousers, ensuring they remain hidden when seated.

8. Confidence and Posture: Stand tall, exude confidence, and maintain good posture. How you carry yourself is as important as your clothing.

What are some outfit ideas to create a smart-casual appearance with penny loafers?

Creating a smart-casual appearance with penny loafers allows you to strike a perfect balance between sophistication and comfort. Here are some outfit ideas to achieve this versatile look:

1. Chinos and Dress Shirt: Pair slim-fit chinos with a well-fitted dress shirt. Leave the shirt untucked for a relaxed vibe, and roll up the sleeves for a touch of informality. Add a leather belt that matches your penny loafers for cohesiveness.

2. Blazer and Jeans: Combine dark, well-fitted jeans with a smart blazer. Add a crew-neck sweater or a casual knit tie for extra style. Penny loafers elevate this classic combination while maintaining a casual undertone.

3. Lightweight Suit: Opt for a lightweight, unstructured suit in a subtle pattern or earthy tone. Skip the tie and pair it with a crisp, open-collared dress shirt. The penny loafers add a relaxed elegance to this ensemble.

4. Polo Shirt and Trousers: Wear a classic polo shirt with tailored trousers. This combination strikes a balance between casual comfort and polished style. The penny loafers provide a finishing touch of refinement.

5. Casual Sport Coat: Pair penny loafers with a casual sport coat, a plain T-shirt, and well-fitted chinos. This ensemble effortlessly blends relaxed and sophisticated elements.

6. Cardigan and Slacks: Combine a lightweight cardigan with slim slacks for a comfortable yet refined look. Penny loafers enhance the overall aesthetic, making it suitable for various occasions.

7. Tassel Loafers with Shorts: For warm weather, experiment with tassel loafers instead of traditional penny loafers. Pair them with tailored shorts and a lightweight button-down shirt for a stylish, summer-ready appearance.

Can penny loafers be worn by both men and women, and what styling tips apply?

Penny loafers are a unisex footwear style that can be worn by both men and women. Their classic design, comfort, and versatility make them suitable for a wide range of outfits and occasions.

Styling Tips for Men:

Formal: Pair black or dark brown penny loafers with a well-tailored suit and dress shirt. Add a tie and leather belt for a polished look.

Smart-Casual: Combine penny loafers with chinos or well-fitted jeans, a button-down shirt, and a blazer for a sophisticated yet relaxed ensemble.

Casual: Wear them with shorts and a lightweight, casual shirt or a polo for a comfortable and stylish warm-weather look.

Styling Tips for Women:

Work Attire: Incorporate penny loafers into your professional wardrobe by pairing them with tailored trousers, a blouse, and a blazer. Add subtle accessories for a refined appearance.

Smart-Casual: Combine them with slim-fit jeans, a blouse, and a cardigan for an effortless smart-casual outfit suitable for various settings.

Dresses and Skirts: Penny loafers can add a unique touch to dresses and skirts, whether you’re going for a classic or bohemian look. Opt for a midi or maxi skirt for a trendy appearance.

Summer Outfits: Wear them with shorts, a T-shirt, and statement accessories for a chic summer look that’s both comfortable and stylish.

How To Style Penny Loafers


Mastering the art of styling penny loafers is like unlocking a versatile and timeless fashion secret. These classic slip-on shoes, adorned with their signature strap and diamond-shaped cutout, have remained a staple in wardrobes for decades. Throughout this guide, we’ve explored various styling approaches for both men and women, showcasing how penny loafers can seamlessly transition from formal to casual settings.

From pairing them with tailored suits for a sophisticated business look to donning them with well-fitted jeans and a blazer for smart-casual elegance, penny loafers are incredibly adaptable. Their ability to blend comfort and refinement makes them an indispensable choice for a variety of occasions.

Furthermore, penny loafers have shown us that they transcend gender boundaries, offering a touch of timeless style to both men and women. Whether you’re enhancing your work attire, elevating your casual ensemble, or seeking a unique addition to your wardrobe, penny loafers can meet your style needs.

Remember, the key to mastering the art of penny loafer styling lies in choosing the right pair, coordinating colors, and maintaining proper fit and comfort. By following these guidelines, you can confidently incorporate penny loafers into your personal style, making a stylish and sophisticated statement wherever you go.


About Us

Once you have a good idea of the type of bubble slides you’re looking for, it’s time to start shopping. They are comfortable, stylish, and versatile, making them a great addition to any wardrobe. One of the best places to shop for bubble slidess is online, where you can find a wide variety of styles, colors, and sizes. 

You can also find bubble slides on websites like Etsy, which offer unique and handmade options. With so many options available, you’re sure to find a pair that fits your style and budget.

Social Media

Most Popular

Get The Latest Updates

Subscribe To Our Weekly Newsletter

No spam, notifications only about new products, updates.




Sophia is a creative and passionate entrepreneur who is the founder and CEO of Bubble Slides, a rapidly growing company that designs and produces innovative and eco-friendly children's water slides. She continues to innovate and improve her products, always keeping in mind the well-being of children and the environment.

Back to Top
Product has been added to your cart