Clothing and logos are gained by winning a game AND reaching $10k in prize money. I won several games under $10k and and never got the chance to pick a prize. I believe there are 43 clothing articles and logos to win which if you are playing single player games without AI, you should get easily on your way to:
If you want to get there a little bit faster, winning the minigames (need at least one more player: AI or real) will give you random prize. This significantly speeds up the process.