When it comes to style, men face a sartorial conundrum: Stick to classics and risk looking as dull as every other suit in the room; go stylish and get dismissed as a foppish dandy or indie rocker. New Georgetown-based online shirt company Hugh & Crye offers a middle ground, pairing cool, throwback details — sharp spread collars, punchy plaids and stripes — with Italian fabrics and an inventive slim-fit system designed to take unflattering fullness out of button-downs. But while the line’s debut collection, which includes 11 different styles, priced $65 to $115, boasts fashionable flair, it deliberately steers clear of any flamboyancy. “We ask, ‘Can you see Sinatra wearing that?’” says co-founder Pranav Vora of the brand’s retro, Rat Pack influence. “If the answer is no, it doesn’t go.”