How is it September already?

Honestly. Where did August go? The weather this week has been cool, and I'm worried about how much longer I can wear summer stuff. Having had to wear business-y work clothes for the bulk of the last 3 months, I feel like I haven't had the chance yet to wear all my cute warm-weather gear. It's making me so aware of the whole seasons thing. Those new style sandals I never got around to buying? Well, missed the train on that so now I'm debating if I need a new pair of flats or if I should jump ahead to boots? Stood in the Target shoe dept for about 20 minutes today, having an honest internal crisis:

I got to thinking about when it actually gets cold and whether flats are going to cut it. I sort of wore them here in Baltimore in Jan/Feb but they don't cover your feet and forget it if is wet or snows. So I got the rain boots which are fantastic for those conditions. But Philly is going to be colder, and I can't wear wellies all the time (like when I go out or just everyday errands) so what do I do? I found flat boots at Target, but they were just a little below the knee and I got to thinking whether I could wear them with all of my jeans because they don't all tuck in well and then I saw ankle boots. And here is my dilemma- On principle I don't like ankle boots because I think they are a bit silly but they are starting to make more sense. They cover your foot more than flats do but they aren't as high/restrictive as a taller boot. Anyways, I stood there debating over and over and had to really pull myself out of there to avoid an impulse purchase when I wasn't totally gung ho on either. I suppose I can wait until it is actually cold out and then see what everyone else does. I bet that would be a good idea. However, I welcome comments about the taller boot/ankle boot debate.

Why does fashion in the NE get me so anxious? This post is reminiscent of the leggings and tights worrying from a few months ago which resulted in my not actually buying any at all. oy.