I love the look of this Gryson Olivia Handbag because it seems to convey a sense of purpose and functionality, but not at the expense of style. It is made from soft, black calfskin and has two braided top handles, as well as a longer buckled shoulder strap to give you some versatility when carrying it. The zip-top opening reveals a suede lining and pockets both inside and out. It is only 17″ x 13″, so it is a convenient size for using as a carry-on bag when traveling or simply taking out to a casual lunch with friends. And as the leather wears in and begins to supple even more, it just might become the kind of bag that you never want to leave your side. Price: $855.