Best of Boston

Best Dressed

Ashley and Katie Hess

The twin daughters of Linda Holliday (a.k.a. Bill Belichick’s main squeeze) aren’t afraid to take a risk and make it look effortless—be it with over-the-top [...] read more»

2001 Best Dressed

Jack Connors

You want retro? Connors showed up at pal David D'Alessandro's book-signing in a toga. read more»

1997 Best Dressed, Man

Rick Pitino

He has a predilection for classics like Giorgio Armani, and often screams from the sidelines in an exquisitely cut Brioni suit. Pitino prefers to shop [...] read more»

1997 Best Dressed, Woman

Michelle Kessler

She always looks great, but never "too styled." Wife of Kessler Financial Services' CEO, this Kessler is often seen on charity boards sporting Armani, Prada, [...] read more»