Men’s Penny Loafers with Tassels: The Hybrid Style Making a Surprising Comeback

On the other side of the family tree is the tassel loafer. This style is characterized by decorative leather tassels typically placed on the vamp (the upper front part of the shoe). Often, they also feature a strip of leather lacing that runs around the shoe’s collar, finishing in the tassels at the front.

The tassel loafer’s origin is a bit more specific. Its creation is generally credited to the Alden Shoe Company in the late 1940s. Legend has it that Hungarian actor Paul Lukas, known for his dapper style, brought a pair of Oxford shoes with small leather tassels on the laces to a couple of shoemakers. He liked the decorative touch and wanted a similar detail on a slip-on shoe.

These shoemakers then approached Alden, asking them to develop such a style. Alden designer Arthur Tarlow Sr. took on the challenge. He adapted a moccasin-style shoe, incorporating a decorative leather cord that ran around the shoe’s opening and ended in a pair of tassels on the vamp. The resulting shoe, released around 1950, was an immediate success, particularly among stylish men on the East Coast.

Tassel loafers quickly became popular as a slightly dressier alternative to the penny loafer, often favored by lawyers, businessmen, and those who wanted a shoe that conveyed relaxed elegance. The tassels added a touch of personality and visual interest that the simpler penny loafer lacked. While still a slip-on, the tassels gave them a subtle formality, allowing them to be worn with suits as well as more casual attire.

Now, let’s get to the main event: the penny tassel loafer. As the name suggests, this shoe combines features from both classic styles. It typically features the classic saddle strap with the diamond slit found on a penny loafer. However, it also includes decorative leather tassels, usually placed atop the vamp, sometimes emerging from beneath or flanking the saddle strap.

This fusion creates a shoe that’s more visually complex than a standard penny loafer but perhaps slightly less formal than a dedicated tassel loafer with its perimeter lacing. The presence of both the saddle strap and the tassels provides a unique aesthetic. It’s a shoe that seems to say, “I appreciate tradition, but I’m not afraid to have a little fun.”

The specific design can vary. Some penny tassel loafers might have the tassels positioned directly on top of the saddle strap, almost threaded through the slit. Others might have the tassels placed just below the strap, or slightly to the sides. Regardless of the exact configuration, the key is the simultaneous presence of the iconic penny strap and the playful tassels. This combination is what defines this particular hybrid style.

Pinpointing the exact origin of the penny tassel loafer is a bit trickier than its parent styles. While Alden is credited with the original tassel loafer in 1950 and G.H. Bass with popularizing the penny loafer much earlier, the combination of both elements seems to have evolved gradually within the broader loafer landscape.

It’s likely that as both the penny and tassel loafer styles gained popularity throughout the mid to late 20th century, shoemakers and wearers alike began experimenting with combining design elements. The penny loafer offered a solid, widely accepted base, and the tassel provided an easy way to add a decorative flourish.

While not as historically documented as the individual styles, the penny tassel loafer likely emerged as a natural evolution, a way to offer a shoe that captured the essence of both popular designs. It probably gained traction among those who appreciated the classic look of the penny but desired the added visual interest and personality of the tassels.

Over time, the penny tassel loafer found its place, albeit a slightly less prominent one than its parent styles. It became a choice for those who wanted something familiar yet distinct, a shoe that could bridge the gap between the straightforwardness of a penny and the overt decoration of a traditional tassel loafer. Its history is less about a single inventor and more about the gradual blending of successful design elements within the evolving world of men’s footwear.

The appeal of the penny tassel loafer lies in how its seemingly disparate elements come together. It’s a study in combining simplicity with ornamentation. The clean, classic lines of the penny saddle provide a solid, traditional foundation. This familiar element grounds the shoe and links it to a long history of accessible style.

Simultaneously, the tassels introduce movement, texture, and a touch of playful sophistication. They break up the visual expanse of the vamp and add a dynamic element that a plain penny loafer doesn’t have. The tassels catch the eye and give the shoe a bit more personality.

This combination works because the elements complement rather than compete. The strap provides structure and a focal point, while the tassels offer a decorative flourish that enhances, not overwhelms, the basic loafer shape. It’s a balancing act – the simplicity of the penny keeps the tassels from feeling overly fussy, and the tassels prevent the penny from being too plain.

The arrangement of the saddle strap and tassels is key to the shoe’s aesthetic. Typically, the saddle strap sits across the widest part of the vamp. The tassels are then positioned either directly on top of or just in front of the strap. This placement creates a layered effect, drawing the eye to the front of the shoe.

In some designs, the tassels might be relatively small and neat, offering just a subtle detail. In others, they can be larger and more prominent, making a bolder statement. The size and style of the tassels significantly impact the overall feel of the shoe, moving it from subtly accented to overtly decorative.

The material of the tassels, usually leather, often matches or complements the rest of the shoe’s upper. This consistency helps integrate the tassels into the design rather than making them look like an afterthought.

Like other loafers, penny tassel loafers come in a variety of materials, each offering a different look and feel. Calfskin leather is the most common choice. It’s durable, polishes well, and develops a beautiful patina over time. Different finishes on calfskin, like smooth, corrected grain, or pebble grain, can drastically change the shoe’s formality and texture.

Suede offers a softer, more casual alternative. Suede penny tassel loafers have a relaxed elegance and are particularly well-suited for spring and summer or for adding texture to an outfit in cooler months. They require different care than calfskin but offer a distinct visual appeal.

Other materials like cordovan (a premium, exceptionally durable leather from a horse’s hide), exotic skins, or even textiles can be used for more luxurious or fashion-forward versions of the penny tassel loafer. The choice of material profoundly affects the shoe’s look, feel, durability, and price.

Beyond the upper, the way the sole is attached to the upper is a critical technical detail that impacts the shoe’s durability, flexibility, and ease of repair. This is known as the construction method.

One common method is the Blake stitch. In this construction, the upper is stitched directly to the sole from the inside of the shoe. This creates a very flexible and close-cut sole, giving the shoe a sleek profile. Blake-stitched shoes are generally lighter and more flexible from the start. However, they are typically less water-resistant than welted shoes, and resoling requires a specialist Blake machine.

Another prominent method is the Goodyear welt. This is considered a hallmark of quality shoemaking. A strip of leather (the welt) is stitched to both the upper and the insole. The outsole is then stitched to this welt. This creates a sturdy, durable, and water-resistant shoe. Goodyear welted shoes can be easily resoled multiple times, significantly extending their lifespan. They are generally stiffer initially but mold to the wearer’s foot over time.

There are also other constructions like cemented (where the sole is simply glued to the upper, less durable and harder to resole) and moc-toe construction (where the upper is formed from wrapping a piece of leather around the foot, often used for the main body of a loafer before the sole is attached). Understanding the construction helps in evaluating the shoe’s quality and longevity. A well-made penny tassel loafer using a Blake stitch or Goodyear welt will be a worthwhile investment.

The penny tassel loafer’s comeback isn’t random. Several factors in the current fashion climate have aligned to bring this hybrid style back into vogue.

One major driver is the shifting landscape of dress codes. The lines between formal, business casual, and casual wear have blurred considerably in recent years. Many workplaces have adopted more relaxed standards, and even traditionally formal events sometimes allow for more personal expression in dress. This “smart casual” revolution creates a perfect environment for a shoe like the penny tassel loafer, which comfortably straddles the line between dressed up and laid-back. It offers more personality than a plain dress shoe but is more refined than a sneaker.

Influence from style icons and social media also plays a significant role. As menswear enthusiasts and celebrities showcase less conventional footwear choices, styles like the penny tassel loafer gain visibility and desirability. Seeing them styled well in different contexts on platforms like Instagram or in fashion magazines helps introduce them to a wider audience and provides inspiration on how to wear them.

Furthermore, there’s a growing desire for versatility and personality in footwear. Modern consumers often seek items that can work in multiple settings and reflect their individual style. The penny tassel loafer fits this perfectly. It’s a shoe that can transition from a business meeting (in the right setting) to a dinner date to a weekend outing, all while adding a touch of unique character that sets it apart from more standard options. It’s a way to signal confidence and a nuanced understanding of style. People aren’t just buying shoes; they’re buying pieces that express who they are.

One of the greatest strengths of the penny tassel loafer is its versatility. While it has a unique look, it can be styled successfully with a wide range of outfits.

With Tailoring: Suit Up (but make it modern)

Yes, you can wear penny tassel loafers with a suit, but it requires a modern approach. They work best with suits that are slightly less formal than your sharpest business attire. Think suits in fabrics like linen, cotton, or even a textured wool. They pair particularly well with suits in shades of navy, grey, or brown.

The key is to ensure the suit isn’t overly structured or formal. A slim or tailored fit for the suit trousers helps maintain a clean line down to the shoe. Avoid overly shiny or formal suit fabrics, which can clash with the more relaxed nature of the loafer. This pairing strikes a balance between sharp tailoring and approachable style.

With Business Casual: Blazers, Chinos, and Shirts

This is where the penny tassel loafer truly shines. It’s an ideal shoe for business casual environments. Pair them with chinos or tailored trousers, a button-down shirt (with or without a tie), and a blazer or sport coat.

The loafers add a touch of sophistication that elevates the look beyond standard casual wear. They work well with classic business casual colors like navy, khaki, grey, and white. You can also experiment with patterned shirts or textured blazers; the loafers are versatile enough to handle them.

With Smart Casual: Jeans, Sweaters, and Polos

Don’t be afraid to dress down your penny tassel loafers. They can look great with smart casual outfits, adding a refined touch to more relaxed pieces.

Pair them with well-fitting jeans (dark wash or selvedge denim works well) and a sweater, polo shirt, or a casual button-down. The key here is “well-fitting” – avoid overly baggy or distressed jeans if you want to maintain a smart appearance. They also work with corduroy pants or even tailored shorts in warmer weather. This combination elevates casual basics, showing you’ve put thought into your look.

Sock Situation: To Sock or Not to Sock?

The sock question is a common one with loafers. For penny tassel loafers, both options can work, depending on the outfit and the occasion.

For a more traditional or business casual look, wearing socks is recommended. Choose socks that complement your trousers or add a subtle pop of color or pattern. Think classic options like navy, grey, or argyle. Avoid thick athletic socks.

For a more casual or summery look, going sockless (or wearing no-show socks for comfort and hygiene) is perfectly acceptable. This is often the preferred look when wearing them with chinos or jeans in warmer weather. Just make sure your loafers are comfortable enough to wear without socks and consider using shoe trees to help absorb moisture.

Color Coordination: Matching Shoes to Outfits

Matching the color of your penny tassel loafers to your outfit follows general rules of footwear color coordination, but with a bit more flexibility due to the shoe’s hybrid nature.

Brown loafers are incredibly versatile and pair well with blues, greys, greens, and earth tones. Different shades of brown, from light tan to dark chocolate, offer varying degrees of formality.

Black loafers are more formal and work best with black, grey, or navy outfits. They tend to lend a sharper, more classic feel to an ensemble.

Burgundy or oxblood loafers are a fantastic way to add color and personality. They pair particularly well with navy and grey and can be a great alternative to brown or black.

Ultimately, trust your eye and don’t be afraid to experiment. The penny tassel loafer is a shoe with character, and your styling should reflect that.

Investing in a good pair of penny tassel loafers means considering several factors beyond just the style. Quality materials and construction significantly impact the shoe’s look, feel, and longevity.

Material Quality: Grain, Patina, and Durability

The quality of the leather is paramount. Look for loafers made from full-grain leather, which is the strongest and most durable part of the hide. It has natural variations and imperfections that contribute to its character and develop a rich patina (a soft sheen that develops on the surface through use and exposure) over time.

Corrected grain leather, while appearing flawless, has had the natural grain buffed away and an artificial grain stamped on. It’s less durable and won’t develop a patina like full-grain leather.

Suede quality is judged by its fineness and evenness of nap (the raised fibers on the surface). Good suede feels soft and luxurious.

Examine the leather for any signs of cracking or stiffness. High-quality leather will feel supple and substantial.

Construction Method: Understanding Welted vs. Cemented

As mentioned earlier, the construction method is a key indicator of quality and durability.

Goodyear welted loafers are generally the most expensive due to the labor-intensive process, but they are also the most durable, water-resistant, and easily resoleable. They are an investment that can last for many years with proper care.

Blake-stitched loafers offer a sleeker profile and more flexibility, often at a slightly lower price point than Goodyear welted shoes. They are also resoleable but require specialized equipment.

Cemented loafers are typically the least expensive. They are lightweight and flexible but the least durable and often not designed to be resoled. These might be suitable for occasional wear or if budget is a primary concern, but they won’t last as long as welted or Blake-stitched options.

Check the stitching on welted or Blake-stitched shoes; it should be neat and consistent.

Fit and Comfort: The Importance of a Proper Fit

Proper fit is crucial for any shoe, but especially for slip-on styles like loafers. Penny tassel loafers should fit snugly but not uncomfortably tight. They should stay on your foot without excessive slipping in the heel.

Leather shoes will stretch and mold to your foot over time, but they shouldn’t be painfully tight from the start. Try them on later in the day when your feet might be slightly swollen. Walk around in them to ensure there are no pinch points or rubbing. A well-fitting loafer will be comfortable from the moment you put it on, or require only minimal breaking in.

Details Matter: Tassel Size, Shape, and Placement

Finally, pay attention to the details specific to the penny tassel style. Look at the size, shape, and placement of the tassels. Do they feel proportionate to the shoe? Are they neatly made? The quality of the tassels themselves, and how securely they are attached, indicates the overall attention to detail in the shoe’s manufacturing. The design of the penny strap – its width and the shape of the slit – also contributes to the shoe’s overall aesthetic.

Proper care is essential to ensure your penny tassel loafers last and continue to look their best.

Cleaning Different Materials (Leather, Suede)

For calfskin leather, regularly wipe down your loafers with a damp cloth to remove dirt and dust. For more thorough cleaning, use a dedicated leather cleaner according to the product’s instructions.

For suede, use a suede brush to gently remove dirt. For stubborn marks, a suede eraser can be effective. Avoid water, as it can stain suede. If they do get wet, let them dry naturally away from direct heat.

Conditioning and Polishing (Explain products)

Leather loafers benefit from regular conditioning to keep the leather supple and prevent drying and cracking. Use a leather conditioner or cream, applying a small amount and rubbing it in with a soft cloth.

For a polished look, use shoe polish that matches the color of your loafers. Apply thin coats, let them dry, and then buff to a shine with a brush or cloth. Polishing also helps protect the leather.

Suede does not require polishing, but you can use a suede protector spray to help repel water and stains.

Storing Your Loafers (Shoe trees)

When you’re not wearing your loafers, store them properly to help them maintain their shape and absorb moisture. Shoe trees, particularly those made from cedar wood, are invaluable. Cedar absorbs moisture and helps prevent odors, while the tree itself helps the shoe keep its form and reduces creasing. Insert shoe trees immediately after wearing, while the shoes are still warm and contain moisture from your feet. Store your loafers in a cool, dry place away from direct sunlight.

Penny Tassel Loafers vs. Other Loafer Styles

It’s helpful to understand how the penny tassel loafer fits into the broader world of men’s loafers by comparing it to its cousins.

The traditional penny loafer is the simplest and generally most casual of the classic loafer styles. Its clean lines make it highly versatile, but it lacks the decorative element of tassels.

The traditional tassel loafer, often featuring perimeter lacing ending in tassels, is typically considered slightly dressier than the penny loafer due to the added ornamentation. It has a more overt personality than the penny.

The penny tassel loafer sits somewhere in between. It has the recognizable foundation of the penny strap but adds the visual interest of the tassels. It can be dressed up more easily than a simple penny loafer but might be considered slightly less formal than a traditional tassel loafer with extensive lacing, depending on the specific design.

Bit loafers, characterized by a metal horsebit across the vamp (famously popularized by Gucci), are often considered the dressiest of the classic loafers. They have a sleek, refined look due to the metal hardware.

The penny tassel loafer offers a distinct alternative to these other styles. It’s for the man who appreciates the heritage of the penny loafer but wants a bit more personality than the classic version provides, without going for the full ornamentation of a traditional tassel or the metallic detail of a bit loafer.

Given the current trends towards versatile, comfortable, and personality-driven footwear, the future looks bright for the penny tassel loafer. Its ability to bridge the gap between casual and smart settings makes it a relevant choice for modern life.

As menswear continues to embrace a mix-and-match approach to style, the penny tassel loafer fits right in. It can be a statement piece or a subtle detail, depending on how it’s styled and the specific design of the shoe. We may see more variations emerge, with different materials, sole types (like chunky commando soles for a more rugged look), and tassel designs.

While it may never reach the ubiquitous status of the classic penny loafer, the penny tassel loafer is carving out its niche as a stylish, interesting, and surprisingly practical option for the discerning man. Its comeback isn’t just a fleeting trend; it seems to be a recognition of its inherent versatility and character.

The men’s penny loafer with tassels is a prime example of how combining classic elements can create something fresh and relevant. It takes the understated cool of the penny loafer and blends it with the subtle panache of the tassel loafer, resulting in a shoe that’s more than the sum of its parts.

Its resurgence is a testament to its adaptability in an era of evolving dress codes. It offers a way to express personal style while remaining polished and put-together. Whether paired with tailoring, business casual separates, or smart casual outfits, the penny tassel loafer adds a touch of nuanced elegance.

Choosing a quality pair and caring for them properly will ensure they become a valuable and long-lasting addition to your wardrobe. So, if you’re looking for a shoe that’s classic yet distinctive, versatile yet full of character, it might be time to consider welcoming the surprisingly stylish penny tassel loafer into your rotation. This hybrid is definitely back, and it’s ready to make a statement.