Kate, I've a feeling the wide striped shirt isn't helping with the shoulders in #1 I think you also wear softer cuts and fabrics than I do which I'm sure helps minimize the IT effects with that type of tucking. For what it's worth I don't think I've ever thought your shoulders look super broad with that type of tucking.
Elly, that's what I see as well! So I'm thinking maybe it's not the vibe of the outfit that he's reading as masculine, but whether or not the outfit gives me a "masculine shape" (shoulders seem to be the major determining factor of that, based on our discussion), if that makes sense.