The main issue for me would be trusting the female approving the shirt. I suppose you could have a collection of people, each with a portfolio, but it's a bit of a catch 22: I have to pick a woman whose taste I like, but I am only using the service because I have poor taste in fashion. One way around that would be to simply have a "style" that people want to fit. I might know if I live in NYC that I want the "Wall St…
He's a better idea. Instead of choosing a woman whose taste you like, you should be able to choose a woman whose personality / interests / etc you like. Hopefully that'll correlate to you wearing clothes that that sort of person likes?