How to Style the Sperry Gold Cup Collection

Six looks to take you from day to night, desk to dock.

Sperry
April 9, 2018
in Style

Say hello to fashion, fellas. Choice shoes plus choice styling = supreme confidence. Day to night. Desk to dock. Done and done. We’re breaking it down.

The Gold Cup Collection is the most elevated expression of the Sperry brand. Think: premium everything – the best leathers, the most careful construction, and obsessive attention to comfort. Once you’ve dialed up your shoe game, you’ll want to elevate your style to match (we know we do).

Mr. Clean

Keep things crisp + streamlined with double denim. Try buttoning your shirt to the top but rolling the sleeves for an unexpected, dressed-down look. Cuffing works great on straight leg denim (and shows off the premium detail of your shoe, too). If it’s cold, add a contrast top layer like an olive bomber jacket or an open trench.

Gold Cup Captain's Oxford

The Renegade

For a classic, nautical-inspired look, go for stripes – in navy and white, of course. A utility jacket adds modern edge; try it unzipped with the sleeves pushed up. Pair with dark raw denim, rolled twice at the hem to reveal the raw edge inseam. The oxfords are the pull-it-together hero.

Gold Cup Captain's Oxford

Scratch Player

Play up the casual vibes of the luxe Haven sneakers with a jersey blazer – it looks polished but relaxed. Up the sportiness with a hoodie underneath (yes, hood and drawstrings out!). A pant with side detailing looks modern, cropped above the ankle to show off your kicks. Pocket square for the win.

Gold Cup Haven

Easy Ace

Take the same concept to another level by trading the hoodie for a simple, high-quality striped tee. Not required, but it’s a trick that works every time: the half tuck. Raw denim, finished with a single cuff keeps the effortlessness in tact and lets the shoes be the star.

Gold Cup Haven

The Pro

Our most premium boat shoes play well with other elements that have nautical roots. Channel beach weekend vibes with a classic rowing henley paired with Nantucket red shorts. The colors offer that seafaring feel, and the frayed edge looks cool for your starring role in a table tennis tourney at the beach.

Gold Cup Authentic Original

The Gamer

Take this elevated version of Sperry’s most iconic shoe to the city or a casual Friday at work with a classic white tee under a super clean heathered gray sweatshirt. Pair with a belted, slim cut chino. (And yes, even the sweater can get the half-tuck treatment.)

Gold Cup Authentic Original

Because of the care and attention to detail that goes into them, our Gold Cup line is a lasting investment. And now you have a few new ways to wear them. Show us yours too @sperry using #SperryMyWay.

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