Floyd Mayweather Jr. is undeniably one of the best boxers of all time. He has a flawless 50-0 record following his latest victory against UFC lightweight champ Conor McGregor. As his career progressed and the checks got bigger, his moniker changed from “Pretty Boy Floyd” to Floyd “Money” Mayweather.

In the same span, however, his outfits have gotten noticeably more over-the-top and gaudy, and his fashion choices seem to have taken a downhill turn in general.

Click through to check out some of the champ’s most ridiculous fashion missteps over the years.