ICare is a statement piece, and quiet large. If you already have a few YSL pieces then i would say go for the iCare. If you don't, i would say go for the Medium Envelope or Medium Puffer bag. The Medium Envelope is an absolute classic, looks classy and even elevates a casual outfit. The Medium Puffer is a little bit more casual than the Envelope bag and has a 'cool girl vibe to it'. Due to be a softer bag, the puffer would fit more in than the envelope bag. If you want dressy and luxe, go for envelope. If you want something a little more practical and versatile, go for the puffer. If you need a tote bag most days then go for the icare bag. Hope that helps!