Here, you need to pay extra attention to the durability of the Contrasted Colored Shoulder Bowler Box Bag, you want double stitching wherever possible, you want the leather itself to be extremely durable and also that it ages well. By aging well I do not refer only to actual aging of the bag, but the impact that wear and tear will have on the bag. Some leather messenger bags will just be destroyed and unusable when exposed to harsher treatment while some others will actually look cooler because of that. It all depends on the leather and the craftsmanship of the bag itself.

Last question you should ask, and to some(mostly women though) the most important one is "Will it match with my shoes?"

Some people would just laugh at this question but it is really important. Matching bag and shoes is the staple of fashion and if you look around yourself, you will see that it is the truth. Everyone with style matches their bag and shoes and so should you. I am not saying you need to get exact same color as your shoes but they need to match. This is even more true with leather messenger bags and leather shoes. A good match will turn eyes toward you while a bad match will get you rolled eyes. --- Find more in my leather bags collection.