Best of Boston

In the 21st century, Boston’s been getting used to the idea of dynasties, what with the Red Sox winning two World Series championships and the Patriots a trio of Super Bowls. Mr. Sid has similarly dominated its field: Since 2000 the family-owned men’s clothing mainstay has taken the hardware every year this Best of Boston category has been judged. Add that streak to its continued strong performance in custom fitting (with seven in-house tailors), selection (running from Agave to Zegna), and amenities (free cocktails enjoyed before vast flat-screens), and it’s clear why men are still walking out of Mr. Sid looking like winners.