I am a terrible packer. Most times I'm more of a "throw it in the bag" type of girl. I just grab all the cute clean shit i have in my closet or on top of my dryer (which means i'm a terrible clean clothes putter-upper too) and throw it in the bag.
Every time I am going somewhere, I have really good intentions. I resolve to pack only the essentials. I intend to lay out on my bed one outfit per day, all of which will match a single pair of my favorite brown boots or, at most, a pair of wedges--one dressy-ish, one casual. I usually imagine my packing will result in the look in one of those magazine layouts where five pieces can be combined to make 878 outfits, ranging from comfy casual to elegant comfy casual.
What I do instead is this: start throwing things in my bag(s). Add more items until the bag is unzippable. Pack another overflowing bag full of shoes, some of these shoes have been worn maybe once. Hide more small hair accessories in my purse and/or car trunk. Before i walk out the door, grab any item within reaching distance. Forget all but one crappy hair tie & most of the time my sunglasses and dry shampoo, which is probably the best hair product ever for a lazy ass like myself. I think that I have travelled a respectable amount and, by now, you would think that I could pack one small carry-on bag for a long weekend away. Somehow, I'm not even close. Which also means packing this evening for 9 days out of town will be a real challenge. Beer me.