Back in the late '80s and early '90s my A.O. (Area of Operations for the civilians) in Manhattan was bordered by the Algonquin Hotel to the west and Brooks Brothers to the east. All I needed fell into that two block perimeter. Chipp. J Press. Brooks. JR Cigar. Mr Hoy at the Algonquin Bar. It was a target rich environment for a salesman from Chicago and easy on the shoe leather.
Today, as a resident of Manhattan, my favored A.O. is a perimeter down Lexington Avenue bordered by my barber, Paul Mole at 74th Street (ask for Gary the Russian) to the north and Garnet Wines at 68th Street to the south (where there's a stunning blonde who really knows her Bordeaux and Burgundy). Peter (hold 'em up) Elliot. R.O.P. infested Swifty's. J. McLaughlin. Neils Coffee Shop. Lexington Bar and Book. And a favorite, Roberta Roller Rabbit.
I picked up this RRR shirt last year thinking it screamed Independence. Hand blocked and dried in the sun, it's lighter than the airmail envelopes I remember from the '60s. Same color theme too. Break out the white shorts and boat shoes-- Hard to go wrong. $85 and unique to boot. There's not a lot for men but what there is should meet your sartorial mission for Summer. Avoidance of VV. Their web site is here.