Okay if we are keeping it under $250 then my list is as follows.

$40 comfy shoes
$15 jeans
$5 tshirt
$8 long sleeve shirt
$4 wool socks
$3 normal underwear.
$6 long underwear
$40 warm, heavy coat
FREE as much water as I can possibly squeeze in to a day pack (should be over 2 gallons)
$15 Jansport Daypack
$18 3 3600 calorie mainstay rations
$1 Full-Size Red Bic Lighter
$5 Storm Shelter Instant Pocket Tent
$2 1" x 40" Nylon Web Belt
$1 Reynolds Medium Oven Bag
$8 Rescue Flash Signal Mirror
$2 10 Tinderquik Tabs
$17 True Nord Compass
$7 Inova White LED Coin Cell Light
$2 Spare Battery for Inova LED Light
$2 Colghans Windproof/Waterproof Matches w/ Striker
$1 Non-Lubricated Condom
$3 Small Ferrocerium Rod
$2 2 Benedryl Caplets
$2 2 Anacin Aspirin Tablets
$2 2 Tylenol Caplets
$2 2 Advil Caplets
$1 5 Small Bait-Style Fishing Hooks
$2 Sterile Drop Point Scalpel
$5 9 Katadyn MP-1 Tabs
$6 50' Black 7 Strand 550# Paracord
$1 Large Gaff Hook
$1 5 1"x1" Sterile Isopropyl Alcohol Pads
$2 Bundle 12' Professional Grade Silver Duct Tape
$1 Bundle 12' 3M Black Electrical Tape
$8 Mora Fixed Blade Knife
$8 Opinal Folding Knife

Grand Total $248.00