Men's Gold Cup™

Timeless Style. Everyday Luxury

Crafted to the gold standard, the Sperry Gold Cup™ collection marries heritage techniques with modern day innovation to create timeless classics that elevate any tastemaker’s wardrobe. Our most premium offering combines the very best features of Sperry’s signature anti-slip sole and moccasin stitching, with the addition of premium leathers and supple suedes, meticulously crafted details, and extra cushioned in soles for superior comfort. Whether seaside, countryside or in the city, wherever your day takes you, these added luxuries will add timeless style and wear to your everyday look. When it comes to classics – go for gold.

Our Craftsmanship

1
Optimized Comfort

Soft lambskin linings and extra padded cushioned insoles guarantee each step is taken in ultimate comfort.

2
Premium Materials

The softest, supplest leathers and suedes lie at the heart of exceptional design and construction.

3
Even Better with Wear

Crafted using high-quality materials and an unwavering attention to detail, the classic moccasin construction adds timeless style and wear to your everyday look. Shaping to the foot and developing a rich patina over time, every pair just gets better with wear.

4
Elevated Details

Distinctive craftwork, and unique accents (like 18K gold-plated eyelets - who knew!) come together to elevate classic silhouettes with special finishing touches.

Coastal Casual

For a relaxed, nautical-inspired look, try pairing your Sperrys with tailored shorts and a polo shirt or a striped tee. This style leans into the maritime heritage of the shoes, making it perfect for summer weekends, coastal vacations, or even a casual dinner out. Keep accessories minimal—a simple watch or aviator sunglasses add a refined touch without distracting from the clean lines of your outfit.

Elevated Everyday

For a smart casual outfit, consider wearing your Gold Cups™ with a crisp Oxford shirt—white, light blue, or even pale pink work well—and a pair of slim chinos. Neutral or earthy tones like tan, navy, or olive tend to complement the rich leather of the Gold Cups, especially if you're wearing the brown or tan versions. If the weather calls for it, you can add a lightweight blazer or an unstructured cotton jacket to sharpen the outfit without going full formal.

Introducing the Gold Cup™ Collection

Where superior craftsmanship meets unmatched comfort and style.

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Introducing: The Gold Cup™ Women's Collection

Gold Cup™ 2-Eye Boat Shoe

A bold and luxurious take on our iconic Authentic Original™ Boat Shoe, crafted to the highest Gold Cup-standard.

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Gold Cup™ Driver Loafer

Part boat shoe, part driving shoe. The ladies' Gold Cup Driver brings together two legendary styles, crafted to the highest Gold Cup-standard.

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When it comes to classics – go for gold.

Gold Cup™| Handmade in Maine

Keeping the art of shoemaking alive, it's the experienced hands behind every Handmade in Maine Gold Cup™ shoe that allow you to indulge in life’s little luxuries. Dedicated to the details that matter most, skilled hands transform top-tier leathers and soles into beautiful shoes that honor heritage and celebrate style. American-made and crafted from premium sourced materials, each exclusive style delivers an elevated sophistication to those who appreciate the finer things in life. Refined style, crafted by hand.

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Meet our most premium collection

Gold Cup™| Handmade in Maine