Stacey And Clinton, I Need Help!

I watch What Not To Wear regularly. I cling to The Rules. I go to the stores. I get overwhelmed. I leave with nothing. Or I leave with something really safe, thinking that next time I'll go back and get something a little more stylish to pair with that really safe item I bought. And then I go to the stores, get overwhelmed, leave with nothing or something really safe. Wash, rinse, repeat. And so I have a limited wardrobe that's rather, er, boring and most certainly not very stylish. I don't really care to be a fashion icon but I've realized my wardrobe is looking rather, ahem, matronly. And really, I'm only 38. I'm not ready for matronly.

By following The Rules, I have managed to add a few nice basic pieces to my wardrobe in the last couple of years but that's about it. So how do I break through this block I seem to have when it comes to shopping for myself? I know the kinds of clothes I want to be wearing. It's just shopping for them that gives me trouble. I've often said I wish they'd make Garanimals for adults. I'd be all over that line of clothing.

To give you a little idea of what I'm talking about, this is how a recent shopping trip went. I was looking for a black skirt, khaki shorts and a top.

Here is what I bought:

The shoes are open toe. Hard to tell in the picture.

Do you notice a trend here? Nice pieces but very, very safe. I put it all together with an avacado green cami I have and it makes a nice outfit. And I can mix and match the pieces with some other things in my closet so that's nice. But safe.

So who wants to be my Clinton and Stacey? How do I stop being such a fashion weenie? I have absolutely zero shorts to wear this summer. The city shorts are too long for my legs. Most other shorts I find are too short, to wide in the legs, etc. I have one skirt that I wear to church every Sunday and just switch out the tops. Before the addition of the new capris I had 2 pair of (too big) capris and a pair of jeans that I rotated throughout the week. I've not worn a dress in years because I have such a hard time finding one that's fits well. My wardrobe is sad. Even The Man thinks it needs help. So help me, dear readers. How do you go to stores and pull together a great looking outfit? And if you ever run across that Garanimals for adults line, let me know.