By Bradley Hasemeyer
on 8.30.10

The prep of today is edgy. It’s slimmer, more modern and usually wrapped in a casual—not slouchy—vibe. When looking for that perfect piece of footwear to accompany your Nantucket picnic on the bay, who better than Massachusetts-based Sperry to get your Cape Code on?

Started by an avid sailor who created special grooves in his soles for better traction on wet and icy surfaces after noticing his dog’s ability to navigate an icy lake with no problem, Sperry Top-Sider has been perfecting comfort, performance and style over the past 75 years on its classic (possibly original) boat shoe. To pay respect to the company’s history, Sperry has a released the 75th Anniversary Seamate collection. With its 360-degree lacing, handsewn construction and unique color options (like our seafoams pictured above) these boat shoes go from bar, to Sunday service, to work effortlessly. Oh, and in case you want to spend the $75 on some shorts (with whales), you can get in on a free pair by entering their Facebook contest. Happy sailing.

Buy Now: $75

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