I would spend the extra $100 and get the bag that you really love, the Rebecca Minkoff. Weighing your options is quite sensible, but in the long run it's worth it to have the bag that you've fallen in love with. In terms of looks, I actually prefer the Minkoff - it looks a bit more streamlined, if that makes sense. However, both of the bags are nice and fit the bill, so you can't go wrong with either. I've never bought either brands as I live in Australia, but people seem to think that Dooney & Bourke are of good quality.