Photograph by Darrow Montgomery
Dupont Circle may be the capital of fussy, but step inside Diego’s and you’ll feel transported back to the no-nonsense hair world of half a century ago. In a sense, you are: Diego D’Ambrosio has been operating his barbershop since the 1960s, and the photos crammed onto every square foot of the walls show all the politicians (U.S. and international) and Catholic leaders whom he’s counted as regulars
over those 50 years. Diego eschews the technology, and pricing, of the modern salon in favor of a straight razor and a $20 haircut. Sure, at times Diego and his amici
seem more interested in their unceasing, heavily accented banter than in your coiffure, but that’s part of what you’re paying for.