Penny loafers are a timeless shoe style that can elevate any outfit. With their sleek, low-profile design, penny loafers are versatile enough to wear to the office, out on the town, or just casual weekends.

If you’ve invested in a good pair of penny loafers, you’re probably wondering — how exactly do I style these shoes? Here’s a quick overview: Go for slim-cut pants, avoid socks or opt for low-cut socks, and add a belt for a polished touch.

Read on for a complete guide to styling your penny loafers for any occasion.

Choose the Right Pants for Penny Loafers

When it comes to styling penny loafers, choosing the right pants is essential to create a polished and sophisticated look. The right pair of pants can complement the classic design of penny loafers and enhance your overall outfit. Here are some options to consider:

Slim-cut trousers

Slim-cut trousers are a great choice to pair with penny loafers. They have a sleek and tailored fit that adds a modern touch to your outfit. Opt for trousers in neutral colors like black, navy, or gray for a versatile look.

Slim-cut trousers can be worn with both formal and casual outfits, making them a versatile choice.


Chinos are another excellent option to style with penny loafers. They are comfortable, lightweight, and come in a variety of colors. Choose a pair of chinos in a slim or straight fit for a more polished look.

Khaki or beige chinos are a classic choice, but you can also experiment with bolder colors like olive or navy.

Dark denim

For a more laid-back and casual look, you can pair your penny loafers with dark denim jeans. The contrast between the polished loafers and the rugged denim creates an interesting combination. Make sure the jeans have a slim or straight fit to maintain a balanced aesthetic.

Dark wash jeans work best, as they provide a sophisticated and refined look.

Avoid baggy pants

One important rule to keep in mind when styling penny loafers is to avoid wearing baggy or oversized pants. Baggy pants can overwhelm the sleek and streamlined design of the loafers, creating an unflattering look. Instead, opt for pants that fit well and have a tailored silhouette.

This will ensure that your penny loafers take center stage and complete your stylish ensemble.

Remember, the key to styling penny loafers is to find a balance between sophistication and casualness. Experiment with different pants options and find what works best for your personal style. Whether you’re dressing up for a formal event or going for a more relaxed look, penny loafers can add a touch of timeless elegance to your outfit.

Socks or No Socks with Penny Loafers?

Deciding whether to wear socks or go sockless with your penny loafers is a personal style choice that can greatly impact your overall look. Here are a few factors to consider when making this decision:

No socks for a casual vibe

If you want to achieve a more laid-back and casual look with your penny loafers, going sockless is a great option. This style works particularly well during warmer months or in casual settings. Pair your penny loafers with cuffed jeans or chinos for a relaxed and effortlessly stylish appearance.

Remember to clean and moisturize your feet before going sockless to ensure they look and feel their best.

Low-cut socks if you need them

If you prefer the comfort and hygiene benefits of wearing socks but still want to maintain a more polished look, opt for low-cut or no-show socks. These socks are designed to stay hidden inside your shoes while providing a barrier between your feet and the leather of your loafers.

Look for socks made from breathable materials like cotton or bamboo to prevent your feet from getting too hot or sweaty.

Avoid crew socks

One style mistake to avoid when wearing penny loafers is pairing them with crew socks. Crew socks, which typically reach mid-calf or higher, can visually disrupt the clean lines of the loafers and make your overall outfit appear less put-together.

Instead, stick to no-show or low-cut socks to maintain a sleek and stylish look.

Ultimately, the choice to wear socks or go sockless with your penny loafers depends on your personal style preferences, the occasion, and the overall look you want to achieve. Experiment with different options to find what works best for you and confidently rock your penny loafers in style!

Add the Finishing Touches

When it comes to styling penny loafers, it’s all about the details. Adding the right finishing touches can elevate your look and make a statement. Here are some ideas to consider:

Add a belt

Pairing your penny loafers with a matching belt can create a cohesive and polished look. Opt for a belt that complements the color and material of your loafers. For example, if you’re wearing brown leather loafers, a brown leather belt would be a great choice.

This simple addition can tie your outfit together and give it a polished finish.

Roll up pant legs

For a more casual and relaxed look, consider rolling up your pant legs when wearing penny loafers. This style works particularly well with slim-fitting trousers or jeans. Not only does it add a touch of effortless coolness to your outfit, but it also allows your loafers to take center stage.

Just make sure to roll up your pants neatly and evenly for a stylish effect.

Try a sweater vest or blazer

If you’re going for a more sophisticated and preppy look, layering your penny loafers with a sweater vest or blazer can take your outfit to the next level. A sweater vest adds a touch of vintage charm, while a blazer adds a refined and polished touch.

Both options create a stylish contrast with the casual nature of penny loafers, resulting in a well-balanced and fashionable ensemble.

Remember, the key to adding the finishing touches is to experiment and have fun with your outfit. Don’t be afraid to mix and match different accessories and clothing pieces to create a unique and personalized style.


With their versatility and timeless styling, penny loafers can become a go-to shoe in your wardrobe. Follow these tips to pick the right pants, socks, and accessories to make your penny loafers look sharp.

Experiment with different looks, whether it’s dressing them up with a blazer or going casual with jeans and no socks. With the right styling, your penny loafers will always add a sophisticated touch to your outfit.

Similar Posts