DJ writes: "Club collar - hip, or nana's nightie??" Answer: Hip, we suppose, but hipness is fleeting so proceed with care. The last time these round-collared shirts were big was in the early 20th century, so if they go out of vogue again next season, you literally might not live long enough to see them back in fashion. Conventional wisdom, and the most frequent deployment, says to wear long-sleeved and buttoned up with a jacket, but something about the collar's curvature against a straight lapel doesn't sit quite right aesthetically—and frankly reads a bit as "working woman". We'd avoid the club on a dress shirt and instead go short sleeves, very casual, and open collar. Shown: Gitman Vintage.