Best Men's Hat Store

Blessedly, some things never change: Optimo’s master hatters still craft fedoras, top hats, derbies, and porkpies by hand and with a vintage sewing machine, attracting loyal customers such as Jay-Z, Johnny Depp, and Jack White. Prices range from $395 for an off-the-shelf Milan straw hat to several thousand for a custom topper.

Best Sailing Class

Even if your style leans more Popeye than Kennedy, you’ll feel welcome at this unpretentious downtown yacht club. Other sailing schools might possess one of the following key qualities, but Columbia claims all three: first-rate, U.S. Sailing–­certified instructors; a diverse fleet of boats, including easy-to-maneuver J/22s and 420s; and a kick-ass clubhouse (the 7,000-ton icebreaker … Read more

Best Art Class

It’s not every day that a neighborhood art center offers one-on-one instruction with a rising star. Rodrigo Lara won Mexico’s National Prize of Visual Arts for sculpture in 2010 with a work depicting a tree sprouting ceramic hands in place of leaves. Fittingly, the first assignment in his 10-week class ($305) is to make—what else—a … Read more

Best Dog Groomer

Owner Jennifer Bishop-Jenkins—one of the first certified master groomers in the nation—combines nearly four decades of experience and a gentle touch to treat your pup to what’s likely to be the best do of his life. A favorite of pet parents and vets on the North Shore and beyond, Bishop-Jenkins knows her way around all … Read more

Best Portrait Painter

This Chinese-born artist has been doing impressionistic oil portraits in Chicago for a dozen years. Don’t bother emailing a photo—Qian won’t paint from it. She requires at least six hours of live posing in her Bridgeport studio. “She is a master in painting the richness of the colors of the skin,” says Patric McCoy, a … Read more