Agreed. Monetizing dress.me as a preferred associate of clothing sites, or as a walled garden market where only you can offer select deals, would be far more palatable. I am also in your target demographic, but all I want is an algorithm that tells me when polka dots and stripes don't match.
I'm assuming you're going to monetize by eventually becoming a reseller or acting as an associate of sites you link to (could be wrong). If not, then I would advise this route over charging outright for using your service, as I'd be far more likely to use it that way.
All that being said, I really look forward to your launch so I can try this out. I am exactly your target audience.