Joe Calautti at Rizzo Tailor in Harvard Square will do up working buttonholes, as will Greg Thomajan's tailor at his shop Zareh's in the Financial District. They only do handsewn buttonholes...Zareh does them exactly like Oxxford, which is a brand that they have long carried. Not cheap...something like $20 or $25 per sewn hole. - B Yeah. A month or two ago I had a jacket altered that had three working buttonholes on each sleeve and needed an extra on each. I went to Joe @ Rizzos. For two buttonholes, one additional on each sleeve, it was $35. I think it's more like $60-80 if it's a brand new piece that needs them all done.