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ALAN BEDWELL knows he’s got a good watch on when no one notices it. “You don’t want the watch to wear you,” said the owner of Foundwell, a reseller of vintage luxury knickknacks in New York. To achieve horological humbleness, Mr. Bedwell favors small-case watches, whose faces measure around 32 or 33 millimeters across. Rather than hogging attention like their Brobdingnagian brethren, they wait to be discovered. “It’s nice when your sleeve comes up and people go, ‘Oh, what are you wearing?’” said Mr. Bedwell.
Until…