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“Get lots of compliments on the shoes!!! Very comfortable to wear, plus great style.”

Penny Loafers With A Modern Twist, Hand-Stitched For The Discerning Gentleman

Without a doubt, the penny loafers we have today stand as the true epitome of timeless elegance and effortless sophistication. These iconic slip-on shoes have graced the feet of fashion-conscious individuals for generations, but their journey to fame was not without hurdles. 

Initially relegated to a mere supporting role in a gentleman's attire, the penny loafer shoes struggled to find their place in the fashion world. Rarely seen and hardly appreciated, they lived in the shadows of more popular styles.

Sean and Cameron, two visionary enthusiasts, shared a deep passion for needlepoint penny loafers, driving them to take a bold leap. They courageously invested their savings in initiating an adventurous journey, determined to breathe new life into these classic shoes.

The path they chose was challenging, requiring an unmatched level of quality compared to other footwear of their time. To achieve their goal, Sean and Cameron enlisted the expertise of renowned needlepoint guru, Seth. 

Together, they embarked on a three-year exploration, testing over a hundred different materials. Their unwavering commitment ultimately gave birth to the Old Sport Company, and the rest is history.

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Introducing the Stars and Stripes Penny Loafers

At the heart of The Old Sport lies an unwavering commitment to its exquisite creations. The company boasts an impressive array of meticulously designed penny loafers, thoughtfully catering to the discerning tastes of both men and women seeking unparalleled style and substance.

Among these truly remarkable creations, the Stars and Stripes Penny Loafers stand out as a coveted model, exemplifying a seamless fusion of artistry and impeccable craftsmanship. Each and every pair of these extraordinary loafers serves as a testament to the skilled hands that bring them to life, artfully weaving magic with a single thread. From the needlepoint to the finished product, these loafers are a shining example of the dedication and passion invested in each detail.

  • Crafted with 3mm waxed saddle leather for enduring durability
  • Luxuriously lined with soft cow skin for unmatched comfort
  • 100% meticulously hand stitched needlepoint uppers

Crafted with Passion & Uncompromising Quality

From the very inception of these masterpieces, a delicate art form takes center stage: the timeless craft of hand-stitching. With dedication bordering on devotion, the company's artisans invest 6-8 hours in crafting a single panel and 16 hours for each pair. Guided by unwavering patience and intense focus, their nimble fingers weave the needle through every small opening in the canvas.

But the pursuit of perfection doesn't stop there. True craftsmanship extends beyond the needle to the very essence of the Stars and Stripers Penny loafers: their materials. The artisans handpick the finest, supple-skin leather, ensuring a luxurious feel and a perfect fit that conforms flawlessly to the wearer's foot. 

In a time-honoured tradition, every element of the loafers and accessories is assembled by hand, preserving the legacy of genuine artisanship.

  • Iconic stars and stripes design, a symbol of the American heritage
  • Assembled the old-fashioned way, with a commitment to genuine artistry
  • Part of an exclusive collection, making it a rare addition to any wardrobe
  • Effortlessly complement a range of outfits, from casual to semi-formal
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Putting Customers First, Always.

At Old Sport, they go beyond simply selling penny loafers. They share a deep passion for exquisite craftsmanship and celebrate each customer's unique individuality. 

The company holds itself to the highest standards, ensuring that every item not only meets but exceeds the benchmarks of quality, comfort, fit, and style that they proudly stand by. 

With a heart for its customers, Old Sport Company goes the extra mile to provide a seamless shopping experience. Customers can enjoy the added benefit of free domestic shipping on all orders, Monday through Friday.

Rated 5.0 Based on 1,000+ Happy Customers

Get Your Stars & Stripes Penny Loafers

  • 3MM Waxed
  • Soft Leather
  • Hand Stitched
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What are you waiting for?

Get Your Stars & Stripes Penny Loafers Now!

  • 3MM Waxed
  • Soft Leather
  • Hand Stitched
Get Mine Now