In bars like D.C.'s Smith Point and New York's Dorrian’s, the subtleties of dress are important. Flamboyance need not apply. The women at these establishments are too conservative to be swayed by rare hemlines and elongated anoraks. Instead, they are tied to decades-old visions of "decorum" and cling to standards of dress long skewered by Brett Easton Ellis. Slightly odious, yes, but, their penchant for cable knits and 3am hookups serve as a mild anecdote to personality.
To score these types of women, one must drink just the right amount of adjunct American lager (don't get wasted or, worse, appear too fussy about booze). Smart, tucked shirts also help, especially when a school belt implies sufficient good breeding. Then name drop a shoreline vacation spot (an obscure one, known only to the aspiring 1%), showing signs of family wealth. Allow accessories and footwear to prove personal taste and individual drive.
Boat shoes fail completely. Belgian loafers suggest one feels above the fray (a decent strategy, but there is potential for backlash). Any lace up—derby or brogue—has no place in a late night (upscale) dive. Pick a bit loafer, however, and sail smoothly. These balance continental sophistication with Ivy League sensibility. These also pair neatly with all types of trousers. And, since no doubt D.C. and New York are not the only haunts in the world, basically exist as the international currency for sex. Thus, also function as something of a wardrobe staple.