Hobo handbags are a rare anomaly in the fashion world. Who would have guessed that the bindles carried by hobos would one day inspire one of the most enduring style trends in handbags? True to their name, hobo bags have a very large and relaxed shape. Designers have long since refined the hobo inspiration, so that the hobo handbag is now as stylish as it is spacious. This over-the-top design brings out the best in other bold choices like bright colors or floral handbags. When fashion forward women want to make a big statement, they turn to hobo handbags.