Very sexy photo and model, and I like the desaturated look. My only criticism is thematic -- I wouldn't necessary think she is wearing a man's shirt were it not for the challenge theme.
I don't really like this shot for the challenge. To me, crossdressing is about trying to portray yourself as the other gender, and although flannel shirts are more of a guy thing, it doesn't work for me with the chest exposed.
Nice technicals; appealing (and sensual) overall image. Nonetheless, it's almost a "cop-out" as far as the challenge is concerned: Yes, the buttons are on the right, so we know it's a men's shirt, but, it's still not something we'd be surprised to see a woman in.
sexy shots always do well. Maybe thats b/c most of us are men. I think something more masculine as far as the clothing goes would be better, Tie for instance.
You'll be getting high scores from the guys for sure(including me). Clothing of the opposite sex does not do her injustice AT ALL. Try that with even the best looking male.
This has sort of a snapshot feel to it, IMHO. The slight desaturation isn't really working for me. I think a full blown black and white would have worked better, and maybe have her eyes not in shadow. She is lovely though.