Hmm . . . I haven't been SYC (officially, because I am planning on shopping soon) but I haven't bought anything in months. I tend to spend 2-4 days in the summer shopping till I drop on various trips to larger cities when we travel. I have a bad habit of walking into the stores I can afford and buying anything and everything I like that fits (which isn't much because of sizing issues). I also am more willing to compromise on fit, because I only get to shop in store once or twice a year. I tend to end up with a lot of orphans or things that are "missing" from my wardrobe. I don't buy much though, so it tends to get worn quite a bit, even if I hate it. I also tend to do one or two big online hauls in the f/w with the same type of results.
When online shopping I tend to look around obsessively for something better in the attempt to find perfect items I won't have to return. I often pass over things I love because I am worried about fit. I also will hold off on orders because I don't have the needed mate for an item I am ordering (a cardi to go over it I am also trying to find, ect) and then the item will sell out!
I tend to get very frustrated because I see all the great clothes out there and can rarely find them in my size because usually companies only reproduce "the basics" or a few colors in the tall sizes. In the summer it matters less, because I only need a few long sleeves and long pants-- although sometimes I need to buy a tall size for the width in the shoulders or length in the top. Right now I am drooling over some of the transitional stuff from AT-- but none of the l/s pieces that I need until late april are available in tall!
Right now I have a very scant winter wardrobe, which became a problem this year because I went from living in a warm climate to a cold one. I also learned how much mileage I could have gotten out of a few cardis and l/s tees layered with my light cotton or 3/4 sleeve blouses. Also, I bought a pair of clogs shoes in the fall that are more of a winter weight/color and then quickly realized I could not wear them at all here in the winter because as soon as the snow starts we have ice or mud constantly. I wish I would have saved that money for boots, because I can't see myself wearing the clogs in the spring or summer except with jeans to run quick errands as they are a heavy style.
I also have a winter coat that needs to be returned. It took me months to find one that fit, but now that the true "frozen" season is almost over I am not sure if I should keep it. I am very hard to fit, but I don't want it to look dated or hate it next year!