Clothes and Shoes, Oh My

The way I dress has changed so much over the past two years it's astounding. A complete wardrobe change is a byproduct of losing 185 pounds (to date). None of my old clothes fit anymore but they also don't fit me anymore by and large. That is to say I've had a complete style makeover. Part of that comes from having a completely different body. I can wear things now that I couldn't fit into before, there are many more clothing options open to me. Another and perhaps larger part of this stylistic change comes from changes in my personality. I'm older, more settled and more aware of how I dress and why but also I'm much more comfortable with myself, both because I'm more comfortable with my body and because I'm much, much happier than I've been in many years.

Completely building a new wardrobe from scratch is a time and money consuming project. So I'm slowly building up my clothes collection and thinking about and developing my style of dress (I can't believe I just typed that sentence, how pretentious am I?). Having never been interested in clothes much before I'm really starting at the beginning here. Two things I do know though: first, I very much enjoy wearing skirts and dresses now. This is a shock to the system but I'm just going with it. Second, I will not now nor will I ever wear uncomfortable shoes. I'm not wearing anything pointy toed or high heeled. I want to wear comfortable cute shoes with swirly skirts like Amelie.

I can't pull off Amelie's cuteness but I may be able to rock some Docs with the new skirt I just bought the other day and cop some of her general style concepts.

The point of this rambling story is I need clothes and shoes and I still don't really know where to shop for them. Most of my recent clothes have been bought at J. Jill (I like this store), Eddie Bauer, and LL Bean. All pretty conservative places. I need to branch out, I just don't know where. The "hipper" shops here in town cater to women who are still much smaller than me. That is to say I still can't fit into there clothes for the most part, with the exception of Clay and Cotton, which I love. There have to be some good online stores, any suggestions? Also any suggestions for cute shoes to wear with skirts and non-jeans pants that don't force your feet into unnatural and uncomfortable positions? All information is appreciated please and thank you.