During the golden age of tennis – and we're speaking not of the Borg/McEnroe/Connors/Nastase murderer's row, but of the seventies- and eighties-era journeymen and hacks at country clubs and public courts – wearing a Boast polo shirt earned one a kind of instant, slightly rebellious cachet. Aside from what company founder Bill St. John always said was a Japanese maple leaf logo – never mind that it also looked like a marijuana leaf – the shirts didn't have much that was different from other polos and designer tennis wear at the time. What made them so attractive was a happy accident of branding and demographics: Simply put, anyone you saw wearing one was cool, full stop (picture Chevy Chase's louche, rakish character in Caddyshack, but without the buffoonery).
The brand faded out about the same time as wooden rackets, though, until a couple of preppy 30-something fans put their heads (and their wallets) together in October 2010 and revived the legendary cult of Boast – it's named after a certain kind of squash shot – for the betterment of us all. There's a full array of polos in various colors and stripes to choose from, along with sharp ties and a very well-made blazer. But in the heat of a five-setter – or a marathon session at the club bar – we'll stick to navy pinstripes to keep us cool. [$68; boastusa.com]