25. Manny Ramirez's Baggy Pants/Do-Rag Combo

Debuted: 2001
Famed Appearance: Patrolling left field for the Red Sox

The ethos, “Manny being Manny” certainly spilled over into the fashion world for the Dominican slugger. Working from the top down, Manny's do-rag became synonymous with his dreadlocks, something that would get him in hot water with Joe Torre in L.A. And from the bottom, Manny was known for sporting baseball pants that looked more suited for an MC Hammer video. If skinny jeans are any indication as for what's to come for baseball uniforms, Ramirez got out just in time.