(Bloomberg Businessweek) -- Originally designed by Seaman First Class Paul Sperry in 1935, the nautical slip-on has risen from practical solution to ubiquitous preppy affectation. John Lobb's $1,420 Isle version faithfully maintains useful features such as white soles (to keep decks scuff-free) and an interlaced collar (to ensure a tighter fit), while adding the kind of refinement that comes from more than 150 years in the bootmaking business. The shoe is newly outfitted this year with a fully lined apron on the toe and is now available in suede.
THE COMPETITION
• Brown rubber soles signal that Brunello Cucinelli's $745 boat shoe is not really intended for maritime situations. But on dry land, its leather-lined suede construction and traditional lacing plot a direct course toward understated opulence.
• Blue bloods may want to stick to tried-and-true Sperry. The $160 Camden from its Gold Cup line features full-grain leather, hand sewing, lambskin lining, and white soles. Contrasting colors in dark and light blue are a break from the typical brown color palette.
• For a fashion-forward take on the boat shoe, Gucci designer Alessandro Michele brings his flair for modern bohemian pastiche to a $750 leather model. With thick rubber soles in red, it's part sneaker, part orthopedic.
THE CASE
Built by hand using a 190-step process in John Lobb's workshop in Northampton, England, the Isle bears all the pragmatic trademarks that made boat shoes a seafaring staple—down to a diamond pattern that provides a no-slip grip on its Goodyear-welted soles. Yet with a taller silhouette, elegantly thin laces, immaculate contrast stitching, and an elongated toe, it wears more like a loafer. Consider it polished protection from slippery surfaces no matter what safe harbor you call home. $1,420
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