In Tom Ford for Gucci
This is when Tom Ford first came onto my radar. I still remember this as one of Madonna's majorly iconic looks. The silk trousers, the silk shirt—people weren't doing this at the time. I don't think she's ever looked more gorgeous. Even now, more than 10 years later, she looks so cool! I don't necessarily know if you would see people doing this type of look now. It's very understated for the Video Music Awards because now people go in thigh-skimming dresses, tons of jewelry, tons of makeup, and a platform shoe. But this was just high fashion at its best. I wish more people would dress like this.