No-Skid Scuffle

Top-Sider vs. Timberland

Along with Lacoste alligators and chino trousers, Sperry Top-Sider shoes have come to epitomize the popular preppie look. Invented in the 1930s by a Connecticut yachtsman to help sailors keep their footing on slick decks, the white-soled, dark brown deck shoes have become a favorite with landlubbers from Newport, R.I., to Newport, Calif., who wear them more for status than for safety.

Sperry's dominance of the booming boat-shoe market is not unchallenged, however. The Timberland Co., a family-owned business that operates out of a former mill in Newmarket, N.H., is aggressively...

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