Saw this question pop up in the morning and have spent the rest of the day thinking about bags. Turns out Iām harboring a lot of opinions on them. Like flora I agree that you need one in each size (s/m/l). Additionally as a person who treats my clothes and accessories like trash itās imperative I have a bag that isnāt precious but looks chic. Which is why I always go with a medium sized leather bucket bag in a fun or neutral color. I go through one every 5 years. In college I had my momās 70s Dooney and Bourke, when I moved to New York I treated myself to a Creatures of Comfort (RIP) and recently I scored an OAD bag (also maybe RIP?) off The Real Real. Bucket bags fit everything, but donāt look like youāre schlepping your whole life in there. I also like going bagless and using just a Petit Pli mini pocket that I wear around my neck. Thereās enough room to tuck a card and a key in too. On the XL size I love my Baggu cloud bag. Itās the absolute goat for travel because it also is collapsable!