Hi. I would go with the first one. I like the Resort bag, but since it matches so well with jeans and there was a post that they rub off on it and it is difficult to remove (cleaner is not supposed to be used on Legacy leather), this bag may not last you as long. The white leather is year round and since it is more "neutral", it will be "in" for many years and not scream 2006 in a year or so-just my opinion. I too, am going this weekend to get the Legacy shoulder bag #1 in either whiskey or black. Happy shopping. I do, like the scarf though...