15 Hilarious Celebrity Fails You Won’t Believe

14. Jessica Simpson

This will always be the problem with wearing heels in the city: if you don’t make sure the heel is big enough, then you are going to get stuck in a grate somewhere. Having your foot suddenly drop a few inches is enough to throw anyone off their balance and it definitely looks like it caught Jessica completely off-guard. Maybe next time she’ll wear flats, or avoid the grates.