I'd love to see you saddle up to the bar at one of New York City's tablecloth steakhouses (Peter Luger, Delmonico's, Keens, Sparks, Gallaghers, etc.) and tell the guy behind the stick you're a bartender in Richmond and the men there drink mai tais, manhattans and old fashioneds (with kumquats).
You want to see a deer-in-the-headlights look? The bar back, working a double, would get to make his first and only mai tai, with straws. By the way, your role model, Don Draper, is only a fictional television character played by an actor. You do know that, right? If I run into you at a bar, let me buy you a sloe gin fizz, with straws. Real men, somewhere, drink those.
Marc Wright and Luke Turner make an excellent old fashioned at Fleming's Prime Steakhouse & Wine Bar in Stony Point. You need to go check it out. For research purposes only. Have another driver to get home or to the next establishment.