Reine,
If I may start by my own example, when I photographed weddings I stood at the back of the church waiting for the ceremony to finish so I could start my job , I often longed to be one of the bridesmaids in their lovely dresses some may not have been the most attractive girls but the feeling was wanting to be one of the girls, I guess for people to comment on how pretty they looked. So maybe there's more to it than wanting to be a stunning one off and wear what's she's wearing.
If you turn the situation around what makes an attractive guy to women ? Using your description not many girls would be attracted to your example in guy mode, unclean, unshaven, overweight and wearing clothes that could have been taken from a scarecrow.
We all have a mental picture of our perfect woman or man , if I were a woman I'd like to look like whoever takes my fancy, I'm sure women must at times think if I were a man I'd like his body, or again whatever attracts you in a man. At times girls do crossdress in male clothes if they happen to think their male partner looks good in them. I've had instances where a GF has taken a shirt or jacket because they happen to like me in them.
Going back to your example again you do see women dressed as you describe and they have partners that are perfectly happy with them, they love them to pieces, some of us may shake our heads but that's life !
Most CDers are a fickle lot, we have to deal with the normal male to female attraction and then, there's the part of us that has it's own needs , the problem is those needs tend to change as our CDing evolves, I have French Maid outfits which I don't wear much now, my CDing has evolved with being more open and going out socially, now I'm trying to put together nice outfits that a GG is likely to wear in the same circumstances. It's really great when a GG does make a genuine comment on how nice you look.
Do I want to look like your examples, the answer is no but I try not to look like that in male mode anyway, in female mode I try and wear things that make me look good for my shape. Maybe I'm lucky that my size and shape works OK in either mode. Look back at some of the threads of members who do struggle with their size and shape I feel as sorry for them as I do to the GGs in your description, being female to them is like a mountain to climb,sadly some give up and resign themselves to the closet when they're desperate to be out and about.