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Article: Discover the art of styling penny loafers like a gentleman

Discover the art of styling penny loafers like a gentleman

Discover the art of styling penny loafers like a gentleman

Men have enjoyed the luxury of various footwear for decades. But hardly any shoe style can match the hype of penny loafers. They have been popular for over a century and continue to mesmerize us with their unique charm. In fact, these are the best loafer shoes for men that hold more relevance today than ever before. If you seek a timeless, adaptable shoe that strikes the perfect balance between style and comfort, your search ends at penny loafers.

Penny loafers are an effortlessly versatile style suitable for various social occasions and dress codes. That is why you will find at least one pair of these shoes in a gentleman’s shoe collection. Curious about how to style them? Continue reading for our comprehensive guide to men's penny loafers and you will discover the best possible ways to style them.

Why is it called penny loafers?

Before we begin with the styling guide, let us have an overview of penny loafers to understand them well. G.H. Bass has strong associations with the penny loafer. It is said that he popularized the style in 1936. The shape was inspired by traditional Norwegian fisherman's shoes and Bass wanted to pay homage to its origins. So people started using these shoes as house slippers in America. However, it didn't take long for them to transition into stylish outdoor footwear.


The casual menswear staple status of the penny loafer owes much to Ivy League college students who embraced it as their unofficial uniform. Throughout the '50s and '60s, American college students continued to sport penny loafers on campus, and the trend received additional endorsement from the epitome of prep style, John F. Kennedy! He wore them during his years of presidency.

Penny loafers started getting global recognition from icons like James Dean and Paul Newman to subcultures like mods and even Michael Jackson. Remember his signature moonwalking step? Today, penny loafers retain their charm that seamlessly blends into various styles. The best part is you can buy men's loafers online with thousands of options.

Penny loafer is an evergreen style staple?

Though the penny might not have much purchasing power these days, the timeless style of the penny loafer has endured for good reason. It makes for a fantastic wardrobe addition. It is a substitute for sneakers when you want to style with jeans or chinos. It is the best choice for summer-weight suits as well. For a truly stylish summer look, you can trade in your boat shoes and don the penny loafers with shorts. No need to be overly cautious with your loafers. You can just wear them confidently and be ready to receive compliments.

Ways to style them

Zip sweater and jeans

The quarter zip is a preferred choice for smart casual enthusiasts and it seamlessly goes well with an Oxford shirt or a tee. You can create a classic preppy look with minimum accessories. All you need to do is adopt a tonal approach. Try to coordinate a navy quarter zip with mid-wash jeans to establish a versatile blue base.

Complete the look with a slight turn-up and solid socks. We suggest you go for the black penny loafers to establish a striking contrast against your skin tone and the lighter shade of denim.

Dark penny loafers and dark jeans

Penny loafers can transition from laid-back Sundays to hustling Mondays in minutes. If you pair them with blue jeans, it results in a harmonious and balanced look. Opt for dark-colored jeans that complement the deep, rich tones of the loafers. If you are wondering where to get these shoes then visit the shop-esmee online store. It is the best place to buy loafers online. You can add a final touch with a sweatshirt or a well-fitted, contrasting-colored long-sleeved shirt, such as mustard or grey, to ensure a cohesive look. This charming look is suitable for various occasions such as a day out with friends, family gettogether, and more.

Ever heard of varsity jackets?

In case you want to infuse a preppy style with an athleisure twist, this look can transform you from a street-style influencer to an old-money brat. The key elements include a luxurious varsity jacket crafted from silk and ribbed cotton. You can pair it with rich brown leather penny or tassel loafers.


This look is perfect for occasions where you want to appear relaxed yet well-put-together, like weekend dates or casual drinks with friends.

Style Polo shirt like a king

Take a nostalgic trip to the mid-century era of the penny loafer and choose a pair of wide-leg trousers. Select a neutral color trousers and a striped polo shirt. Ensure the hems are tailored or casually roll them up and don’t be afraid to reveal a glimpse of your socks. You can also go for a knitted polo shirt if you want that royal look.

Lounge suit never appoints you

This look reflects timeless appeal and office-appropriate style. All you need is a well-ironed lounge suit, a white shirt, and a patterned tie. The only distinctive element that sets it apart from the typical office attire is the choice of footwear.

You will realize that a well-crafted, polished leather loafer can effortlessly complement even the most sophisticated two-piece suit without compromising your professional aesthetic. The subtle charm of any dark-colored lounge suit allows the loafers to take center stage.


Bring back the 90s era

If you are a millennial then this look is made for you. You can embrace the lighter shades of loafers with jeans that don't necessarily represent the typical American prep style. Opting for a chunky-soled brown pair is perfect for infusing a grungy vibe into your spring outfit. Pair them with distressed denim, a simple tee, and a black flannel shirt to introduce a touch of 90s grunge to your overall look.

If you want to buy men's loafers online, you must visit today! They have a wide variety of men’s footwear including boots, sandals, slippers, and more.

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