I am very logical and smart but also messy. The question sounds simple, but is complex (the experienced understand this). I am a grad student living in El Paso 30-120F annually. I work in N. Alaska, outside all day - COLD and wet. Summary: Cold Gear:Down jackets, fleece, wicking underwear, thick socks, etc. Wet Gear: Goretex pants/jackets Desert field gear: old pants/shirts, thin shirts, light wicking clothing Sports/Workout: Boardshorts, regular shorts, tshirts, wicking shirts/tights. Casual: t-shirts, shorts, jeans, etc. Dress: the usual. I dress casual(scummy) usually when warm, nicer when cold/ or for meeting/presentation. Some (eg.Goretex), are obvious. My problem is the universal clothes like t-shirts, shorts, wicking underwear stuff, fleece, lots of socks. Is it best to organize by category (socks, tshirts, underwear, jackets), use (cold, desert, workout, dress), or use frequency(most worn, least worn)? I do a bit of all 3 and end up screwy. Looking for optimal efficiecy I appreciate the quick answers. I guess I also want to add this. Seasonal stuff gets boxed and take out when the season comes around. I like srailroad's OCD answer, but I also hate having a drawer that is 1/3 used. Also in daily use (casual dress), which is the most typical, if I go by category, i will be mixing and matching categories for tshirts. One solution is to change habits - If I always show up to school in semi-casual dress, then I can bring workout clothes separately, but I am afterall a grad student, and dont mind being scummy, especially if the tshirt I wear to school can still be worn later when i hit the gym.