Unlockable costumes/items in the game
Once you complete the requirements for the clothing, they're automatically thrown in your closet, in all your safehouses.

Final Cut (New Coventry) houses all of the punk-esque items in the game. Worn In (Bullworth Town) houses more beachy, sporty, and middle classy type clothing. Aquaberry in Bullworth Vale houses all the upper crust type clothing, although until Chapter 3 the only clothes you can get in there are the Aquaberry Sweater and Vest. Unlockable-- How to Unlock
Jimmy's Skeleton Halloween costume-- Beating the mission 'The Candidate' will open up the mission 'Halloween' which unlocks the costume.
Boxing Outfit-- Beat either 'Boxing Challenge' or 'Prep Challenge' in Chapter 2.
Wrestling Uniform-- Beat Gym 1.
School Mascot-- Beat 'Nice Outfit' in Chapter 4.
Orderly Uniform-- Complete 'Finding Johnny Vincent' in Chapter 5.
Prison Uniform-- Beat all the detention mini games at least once.
Grotto Master-- Collect all G&G cards.
Gnome Costume-- Smash all garden gnomes.
Fast Food-- Complete the Burger Joint errand found in Bullworth Vale.
Gold Suit-- Buy all clothing in the game.
BMX Champion-- Complete one of the bike races.
Black Ninja Outfit-- Fill up your yearbook completely.
Green Ninja Outfit-- Hit stuff with projectiles (eggs, etc.) 1000 times.
Pirate Hat-- Beat up pirate on island near Beach House.
Edna Mask-- Destroy 19/19 Tombstones during Halloween
Crash Helmet-- Place 1st in the Kart Race at the Carnival
Red Ninja Outfit-- During Halloween (must be done during Halloween) at Bullworth Academy, complete the Big Prank task
Tiny Swimsuit-- At the Beach House location, find the Preppie with a blue mission on the beach and beat his swimming time
Black Skate Shoes-- Travel at least 50.00km on foot
Firefighter's Helmet-- Pull the Fire Alarm 20 times
Pumpkin Head-- Destroy all the 27 pumpkins during "Halloween Event" They are around the school and inside the main building
Dunce Cap-- Fail three classes in a row
Bike Shorts-- Travel 100K on a bike
Go Kart-- Beat all Go Kart races.
Running Shorts-- Run/Walk 40 KM ingame
Graduation Hat-- Beat all fivel levels of all of your classes.
Black Cowboy Hat-- Give a homeless guy some spare change in Bullworth
Rubber Band Ball-- Collect all 75 Rubber Bands
Werewolf Mask-- Found in a school locker after picking the lock.
Fire cracker in chem set-- Complete Chemistry 1