What to Wear?

I'm in a rut. For a while now, I've been having trouble figuring out what to wear. I'm not a kid anymore so I can't exactly go around dressed like Avril Lavigne. (Wish I could, though!) It would be easier if I was a prep by nature--then I could just live in Ann Taylor and be happy--but that's not my style.

Part of my problem is that I'm not a big clothes shopper anymore so I don't even know what's out there that's both cool yet appropriate for a mom my age. It used to be way more fun to shop when I lived in the city and had a social life--there were places to go where I could wear the fabulous things I bought. Then came the baby/spit-up years when all I wore was old stuff I didn't care about. But now that my kids keep their food down and I'm back to my fighting weight, it's time to get some style back into my life.

The summer is easy because all you have to do is toss on a cute, comfortable skirt and funky sandals to look good. But when it gets colder, I mostly turn to jeans and boring, long-sleeved shirts. Pair that with comfortable (dull) black shoes and you see where I'm coming from. All I really want to do when it's cold is hibernate, so it's hard to get excited about fashion. But I want to spice things up a bit this year. Last winter, I tried black leggings and long sweaters but when you're dragging two little kids around with you everywhere, it can easily look like maybe you're pregnant with #3. No thanks.

Many of the brands marketed to the slightly more mature woman look to me like old lady clothes. Eileen Fisher, anyone? The Gap and Banana Republic are okay but often so boring. Shopping at places like that is what got me into this rut in the first place.

Part of my problem is that the clothes I really want to wear aren't exactly appropriate for an almost-middle-aged mom like me. I'll show you what I mean. Here is my favorite T-shirt (which I haven't worn since 2004 due to mom-hood):

Clearly inappropriate for small children's eyes. And even if the tykes can't read, their moms can and wouldn't appreciate it, I'm sure. Hey, I don't want to make any enemies, I just want to be unique.

                                                   So, while I want to dress like this:                              

  

                                                  I feel pressure to dress more like this:

What's a suburban mom to do?