16 Fashion Risks That Seriously Paid Off

There's a fine line between a risk-taking red carpet look that works — and one that's a worst dressed contender. Toeing that line takes the right combination of daring, flair, and next-level styling finesse to pull off. In other words, making a kooky outfit work ain't easy. But, without fashion risks, these bright-lights events would devolve into a bunch of pretty ladies in designer dresses — and where's the fun in that?

So, we're paying tribute to 16 celebrities who got the risk-to-reward ratio right and actually owned their offbeat outfits. Ahead, proof that fashion favors the bold.