Gentleman’s Attire: Complete the Rockstar Games Social Club "Skin It To Win It" challenge.
Lady’s Finest: Complete the Rockstar Games Social Club "Skin It To Win It" challenge.
Posse T-Shirt: Unlocked when the multiplayer community reaches an unspecified amount of money in The Strike It Rich! Rockstar Challenge.
Red T-shirt with Red Dead Redemption logo: Open a chest in Riley’s Charge.
Sombrero: Shoot an enemy’s hat off their head.
Rockstar Logo T-Shirt: Climb the ladder and open the chest that is in the attic of John Marston’s House