Since1982 wrote: 1. I'd like to get men accepted wearing skirts as a regular garment before jumping into too much dresses etc.
I see no intrinsic harm in pursuing parallel paths so long as the wearer of the garment isn't role-playing or otherwise pretending to be something he isn't. I think that good designs can be done for men's dresses, but that they will -- of necessity -- be
very different from women's styles. Whilst many of us can "appropriate" skirts from the "other side of the aisle", the same will most assuredly not hold true for dresses.
2.I have the notion that if we all start dressing like that picture you posted of the guy in the "dress"/caftan with the lipstick and coiffed hairdo we are going to do damage to acceptance of skirts for men being a viable choice.
Once again, it all comes back to context. I forget the chap's name, and I cannot locate for the life of me his imagery, but he posted a shot of himself in a caftan that made him look like he just came off the Asian steppes along with Ghengis Khan's boys -- and I'd posit that one would not call those blokes "girly" in the least!
Now, speaking directly to the image above in
this thread, I'd have to make a call of androgeny on that one -- and I do not represent that as a bad thing so long as other subtle cues exist to inform the observer of the truth. That being said, most fashion models today are remarkably androgenous, and sometimes deprived of proper context, it'd be understandable that a casual observer might not be able to determine at a glance the sex of the model in question -- and
that's, I suspect, what may put lots of folks off about skirted rigs -- including dresses -- on guys.