What to Wear?

I don't know what to wear. I realize this is a problem most women think they have. They open their closets, pick through the thousands of dollars hanging inside, and debate what to put on. I admit I've done this. I still do this; however, my problem is more real now. Fall is upon us, winter is approaching, and I live some place where I can't wear flip flops year round for the first time in my life. I don't know what to do!

Ok, so I never lived in a place wear I could literally wear flip flops all year, but it was pretty close. SC - flip flops, NO - flip flops, MS - flip flops. NY - no flip flops. I need to buy some boots, and I think I have the pair picked out. We'll see.

As for clothes, I know I need to layer. I just don't want to look like a blob when I'm outside because of all the layers I wear. I suppose I'll have to pick the lesser of two evils, warmth or blob, depending on the situation. My biggest problem, other than footwear, is jackets and coats. I have the body type of thousands of other people in the world. Unfortunately, the fashion world hasn't caught on. Specifically - coats and jackets never fit me in the armpits. It might seem like an insignificant problem, but, trust me, it's horrendous in the winter. In order for something to fit in the armpits, not to mention over a sweater, I have to find something at least two sizes too big which then swallows the rest of me.

I will not let the cold temperatures beat me this winter, but I am a little worried. Don't get me wrong--It will be cold soon and I will freeze, but I will persevere (mostly by staying inside). Who knows? Maybe I'll love the cold weather. My guess is, however, that will not happen until hell freezes over.