Think you're limited to the most basic silhouettes when it comes to the shape of your carry-all? Not so! Bags in unexpected shapes (mimicking a cruise liner or a star, for instance) add just the right amount of intrigue to an outfit without going totally overboard. High-end weirdo bags tend to maintain their elegance while also adding a pinch of interest like Christoper Kane's floral clutch, which maps the outline of the small illustrated bouquet. High-street options tend to be a bit a bit more kitschy like ASOS's pitch-perfect pineapple cross-body, but are cool and current enough not to drag down the rest of your outfit through some retro time-warp. When carrying a bag that commands as much interest as our picks do, it may be best to keep the rest of your look straightforward — that, or you can go completely bananas, it's up to you.