i have the bar stripe mini borough and the oxblood urbane crossbody bag (the small one) and if you are basing your decision soley on versatility, so far I have worn the oxblood urbane more times than the bar stripe borough. I think the bar stripe will be a goto bag for me over the summer though, but I have plans to continue using the oxblood as well. I know I could wear the oxblood year round, I'm sure not everyone would do this though, but I don't generally do "seasonal" bags, the only reason I have not worn the bar stripe borough is because I think it will look better in nicer weather if that makes any sense, also the pebbled leather of the oxblood seemingly can take more abuse, so I have no reservations about wearing it often.
It's kind of a toss up for me. I bought the oxblood first and if I only wanted a bag I knew i could wear all of the time, this would be it, it easily goes with a lot in my wardrobe and feels so chic to wear. However, I loooove the black and white (and grey and tan and gold) of the bar stripe and know it will be a great pop to an outfit, but for me it's probably not one I would use daily, mainly for fear I would somehow ruin it. Sorry that's not much of a clear cut decision, I was lucky I bought both or I would still be going back and forth on it!