This season, nothing looks newer than an old-school court shoe. Case in point: The Grand Kittery Court, a luxury rendition of the classic court shoe with a low-profile upper meticulously made from premium leather and a traditional cupsole re-imagined in flexible, high-traction rubber.

• Leather upper in Black, Irish Coffee, and Ivory; seven-eyelet lacing system
• High-traction rubber cupsole
• Foam-padded footbed