Saw this question pop up in the morning and have spent the rest of the day thinking about bags. Turns out I’m 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 it’s imperative I have a bag that isn’t 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 mom’s 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 don’t look like you’re 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. There’s enough room to tuck a card and a key in too. On the XL size I love my Baggu cloud bag. It’s the absolute goat for travel because it also is collapsable!
