One of the joys of custom made clothing is getting to choose your own details. But there are plenty of subtle yet distinctive embellishments that can be put on bespoke and off-the-peg clothing alike. Any jacket shipped with unfinished sleeves, for instance, is ready and waiting for any button configuration you care to conjure. 

Most alterations tailors will attach either three or four sleeve buttons without even asking. But on sport coats, especially casual ones - by which I mean any that aren’t solid navy - I think having one or two instead is a nice detail. A one-button cuff is predominantly (but not uniquely - see Roger Moore as James Bond and Steve McQueen in The Thomas Crown Affair) a Southern Italian flourish, so I reserve it for summer jackets. 

I associate the two-button sleeve mostly with Ivy style, since I’ve seen a Kennedy or two wearing them, and they turn up on vintage Ivy-esque stuff. The Duke of Windsor’s famous closet picture features one jacket with a two-button sleeve, but it appears to be an outlier in a number of ways. I had to explain to my British and Italian tailors how I wanted the buttons spaced. So until further evidence to the contrary, I am considering the two-button sleeve one of the few elements of Ivy League style I have adopted.

Since it’s a rare style, you might need to give your tailor some close instruction in order to get it right. I think the buttons on my jacket are too close together. Every tailor, even the best ones, tend to accommodate odd requests by making as little change to their default option as possible. So when you ask for two sleeve buttons, they will just proceed as if they were going to give you the standard three or four, and then stop halfway through. But the two-button cuff is more stylish when the buttons spaced further apart, as in the Robert Kennedy photo linked in the previous paragraph. 

Another good thing about this style is that you can try it, and if you don’t like it, undo it, even if the buttonholes are functional. Just add in buttons until you arrive at your standard arrangement. But try it first with just two, because once more buttonholes are cut, they can’t be uncut. 

Quality content, like quality clothing, ages well. This article first appeared on the No Man blog in September 2014.