Does having to send items back bother you? I'm surprised by the popularity of these services. I always assumed people wouldn't want to go through the hassles of going to the post offices to return stuffs every time they order.
I've only sent items back a couple of times (been using it over a year now).
They seem to be really, really smart (devious?!) with the pricing for the individual pieces. If you don't keep all 5 items, they charge you a $25 "stylist fee". The price difference is then not all that large in many cases to keep all 5 items, vs sending a couple back.
I'm sure they tune their algorithms so that items more likely to be kept are the pricier items, and items that you are most likely to send back are the cheaper ones. Or maybe they even vary the prices per customer, based on feedback and prior history, to increase the odds of a "full purchase". If they don't, they should.
Either way though, it saves me hours of shopping at malls or other stores, and usually does reasonably well with the styles and pricing. I like the service overall.
Usually I don't send anything back -- but when I have, I've been able to just drop it in a blue mail box vs. going all the way down to the post office; very easy. I've seen people in my building just leave it down by the mailboxes for the carrier, but I have a blue box on my walk to work and drop it in there.
I guess it does bother me a bit, tho I rarely actually send things back. If I did more often, it might annoy me enough to cancel. But man having clothes that look good that require zero effort on my part is pretty sweet.