I feel the 30 is a much better size and it’s worth twenty dollars to have the extra space. With that said, I don’t think the 30 looks good crossbody and I love and enjoy mine as a handheld. The 25 looks fine crossbody, but there are so many other cuter crossbodies out there. This bag confuses me. I know a lot of people swear by the strap and using it crossbody, but I guess I’m just old-school in thinking it looks best hand-held or not at all. I’d choose a dozen other shoulder or crossbodies over a Speedy. I’ve seen people fumble over the 25 opening and playing Tetris to get their basics to fit. I’ve also seen 30s carried crossbody where the bag seems to stick out a foot from their side and look ridiculous. I seriously have a love/hate relationship with this bag. In regards to the love, the zipper is like butter and ebene is a wonderful, perfect no-brainer when it comes to care. I mean no offense with any of these opinions, and they really are just opinions, but in regards to original question, I’d go 25 crossbody or 30 handheld. And above all, I’d go crossbody with a different bag altogether.