The difference is that Grant was emulating what regular guys at the time were doing by the scores of millions. Depp and Timberlake and Usher, by contrast, can only “get away with it” because they are famous show-biz stars trying to make an edgy fashion statement.
That said, I do dare to wear a seersucker suit on some hot summer days, even though people look at me like I’m an ice cream vendor.