yes and no... I pretty much shop only for the upcoming or current season yes...
I used to have the motto that I would only shop for things I could wear today (weather wise). But I realized that I would always end up at the mall on our first cold and rainy day of the year and end up buying the most gosh-awful sweaters because they were warm and cozy and those 2 factors were clouding my vision. So, I realized that I really need to shop ahead. This year I kicked off the fall/winter shopping season with the NAS in July, and when the random cold days hit in October, I was prepared. Now, I did end up buying a sleeveless shirt dress in October as well, but it was navy and the weather was still very warm, and it is also a good transition piece as I can easily add a cardigan. But no, I would not buy a sun dress in the middle of October. It's tempting, but by the time I would be able to wear it, I wouldn't think of it as new and I'd want the next season's latest and greatest anyway.
So I guess I don't mind shopping a little ahead, but I don't shop after August for summer and I won't shop after February for winter.