Sperry Top-Sider Authentic Original Made in Maine Boat Shoe
Credit: Photograph by Michael Pirrocco

Sperry Top-Sider Authentic Original Made in Maine Boat Shoe

The heavy demands of competitive, professional sailing created a whole new style of clothing – Henri Lloyd jackets, sweaters from the Guernsey Knitwear Company – that provide serious protection against offshore elements. Trouble is, few weekend warrior-type skippers require the hyper-technical performance wear they see every few years at the America's Cup Finals. Enter Sperry Top-Sider, leaders of stateside sailing gear, and its Made in Maine boat shoe.

Despite a deep connection with the United States – Top-Siders were de rigeur in a prep-schooler's closet circa 1983 – the Massachusetts-based shoemaker actually manufactures its iconic Authentic Original collection overseas. But now, sailors and landlubbers alike have the option to bring it all back home. Sure, the Made in Maines are three times the price of the Originals, but what you're paying for is more than just another talking point at the next Figawi: Here, you're getting shoes sourced from American leather that are handmade using the same techniques pioneered 78 years ago.

Mahogany and tan remain the indisputable classic colors, but we recommend distinguishing yourself from the wannabe Kennedy set with these kicks, which are caught somewhere between aquamarine and tropical rain forest blue (thanks for the guidance, Crayola). They look good with denim, even better with khaki, and best where it really matters – outside, J/Boat optional, cocktail mandatory. [$300; sperrytopsider.com]