I agree that the site won't solve the problem it pretends to address if it's just going to ask you what you usually like and feed you similar stuff. However, t

I agree that the site won't solve the problem it pretends to address if it's just going to ask you what you usually like and feed you similar stuff. However, this can and should be bundled with a more assertive counseling activity: "we're not going to force anything down your throat; however, if you're not satisfied with the way you're perceived, and you think your clothing style is part of the problem, we might have some suggestion to offer". Counselling should itself be structured in two levels: * generic help for free ("If you have $PHYSICAL_FEATURE and want to be perceived as more $QUALITY, you should chose clothes which have $CRITERION. Beware that $CONTRAINDICATION". Could be raw text with a couple of diagrams, could be something more interactive) * referral to one-to-one counselors, with a commission on their fee. However, it sounds like a real problem, with real solutions to be provided, to people willing to pay for it (nobody expects to get clothes for free, no freemium competitor will undercut you), and with enough diversification possibilities to find one successful way to grow. As always, and especially for very personal services, flawless execution matters much more than the initial idea.