I like this idea a lot, but seriously - a tweed blazer is your first offering?

Did you A/B test the offering in terms of what your target customer would consider appealing? (I fully realize you may be targeting pretentious hipsters or middle-aged english gentlemen of course. :)

I'd also suggest maybe an "outfit" (shirt, pants, jacket/shoes, etc) instead of just an item too... no idea if that would result in better conversion, though.

At any rate, best of luck to you... I like the direction you are going.