In the photographs used for the Nothing But the Best album, Frank Sinatra can be seen wearing several shirts with club collars (a small detail that I’ve somehow missed before). When he’d loosen up his tie and undo his top button, he’d then also nonchalantly leave his collar pin attached to only one hole.

It’s a bit difficult to find RTW shirts with collar pin holes today if you wanted to recreate this look, and it would probably be easier to just buy a regular club collar shirt and have a tailor add the needed holes: Patrik Ervell has made these a signature piece of his collections, and on the low end you can also find some nice ones from J.Crew and Rugby. J.Press will have you covered on the pins.