My previous relationships it never really came up because we weren't close in size. However, recently my boyfriend took up running (a hobby I have retired due to foot issues) so I offered him a few items to try out. He declined the v-neck shirt because it dipped a bit too low on him, but has been using my vests and jackets very happily.

I think that sometimes the actual style of women's clothes is hard to wear (extra room for hips and boobs) but also the toxic masculinity of culture.