Angie of YouLookFab has posted about preferred shopping categories... I have a few, but mostly I have a much longer list of things that I'm constantly shopping for (and failing to find).
1. Skirts! Especially Anthro skirts... I have a harder time finding enough tops to go with them, though.
2. Dresses! Just as pretty and feminine as skirts, without having to worry about also dressing my top half.
3. Jewelry--always fits! However, I have a problem of always buying similar, delicate-type jewelry, and then having nothing colorful and chunky to add to boring outfits. I prefer fine jewelry, such as diamonds in my everyday watch and sterling silver metals whenever possible, since base metals always end up turning my skin green.
4. Hair accessories (i.e. forks/sticks/clips), because there's not much point in maintaining waist-length hair unless you can play with it.
1. Dress pants. Ugh. I've had some luck recently with the Sloan fit pants at Banana Republic, so I suspect one key may be to size up in the slimmest available cut. I have average thighs but nonexistent hips and a thick waist, so I need pants that are cut nearly straight up and down.
2. Jeans--slightly better than non-denim pants because I can buy hip-huggers that, while they don't particularly flatter my tummy, at least don't constrict it too much. But I need a 29" inseam, which is annoying because it means that 30" petite inseams are too long for flats and too short for heels.
3. Watches... which, since I treat them as fine jewelry, you'd think I would love shopping for watches. But I have certain criteria for a watch that MUST be met, and they usually contradict each other: all stainless steel, 12 points on the face (because I actually use my watch to tell time, instead of my cell phone), and a slim, delicate, lady-like style. The first two criteria are practical essentials but usually lead me to chunky menswear watches, which I hate. Old-fashioned oval ladies watches are also inappropriate. I finally found the perfect watch last year at Kay Jewelers--it's a Citizen Eco-Drive with a rectangular face and two vertical rows of diamond trim--but only after shopping way. Too. Much.
4. Swimwear. Enough said.
5. Bras--my true size is a 32AA (and my actual band size is a 31), but since that size is difficult to find in non-specialty shops, I just try on tons of 32A push-up bras until I find some that mostly fit.
6. Shoes and bags... Both are very hard to fit for me. My feet are size 5 with wide toes but a slim instep (so wide sizes don't fit, even if I somehow managed to find a 5W); in bags, I am constantly searching for the holy grail of both style AND organization. (I'm an obsessive organization freak.)