This just in: looks inspired by actual hobos are the hottest trends in handbags! (Note: stick not included.) Handbag Heaven’s hobo handbag selection ranges from flirty and fun to more business-appropriate, structured bags. Spring for a petite style when the sun is shining bright and the sweaters are in storage; save the larger bags for those cold wintery days when packing some extra gloves isn’t out of the question.