Where to go—and what to ask for—to dial in everything from a new suit to your favorite pair of jeans, with expert advice from our favorite menswear stores across the country.

Gary Drinkwater got his start in 1978 at the world-famous Louis Boston, a menswear institution that recently closed after 85 years. He interviewed for a visual merchandising position, but when that had already been filled, he moved over to sales. It was there that he learned how to be not just a salesman but a consultant. He quickly realized it wasn’t necessarily clothing people wanted, but an experience.