I get overwhelmed if I try to shop anywhere other than my sister's closet in Miami (free clothes in my style that almost always fit!), so I signed up for Shecky's Girls Night Out event in an attempt to force myself to shop.
I failed miserably. I did get a nice goodie bag (books, food, hair accessories, and various cosmetics), but felt confused walking around what was basically an upscale flea market. I was home in less than an hour, without seriously trying to buy anything.
A personal shopper might be the way to go.