Desperately Seeking Fashion Advice

First, a brief look at my fashion history:

When I was in middle school, I got up every day and put together an outfit, something I thought was cute and stylish and looked good on me. Then I did my makeup, carefully balancing the fact that I wanted to look like I was wearing make-up because it's cool to wear make-up in middle school, but I didn't want to look overmade; it was a balancing act. Then, I did my hair. Because it was the early 90's, this involved a very hot curling iron and bangs. Sometimes, there were hot rollers.

Then, one day, I was wearing one of my absolute favorite outfits. There was a bright turquoise ankle length skirt and a bright yellow t-shirt and a bright red button down and a string of red chunky beads. Uber cool. Except. Except, the "cool" girls didn't think so. On this particular day, they were making fun of my outfit and I said, haughtily, "This is the style in New York and Paris." Because, you know, when in doubt, lie, lie, lie. "You're not in New York or Paris," one of the girls (somewhat sensibly) pointed out. "You're in Kentucky and what's in style here is looking like everyone else."

Although I was never one to just try desperately to look like everyone else, that hit me where it hurt. It was undoubtedly the last time I wore that outfit. I parsed out the pieces to other, less outstanding outfits and tried a little harder to blend in. That is, until high school, at which point, I gave up entirely. It was a slow process. It started with the makeup. Gone. Then the curling iron. Gone. Finally the carefully planned outfit. Gone.

By the time I started driving, my morning routine was something like this. Wake up. Dig through the pile of clothes in quest for something mostly clean and not entirely clashing. Run out the door. Munch pop-tarts and brush my hair while driving to school. Take the scrunchie back off my gear shift and put around my wrist in case I needed to put my hair up at some point. That was it. The entire beauty routine.

In college, I managed the addition of pajamas that I could wear to class.

Then, the conundrum:

The point of this history is to let you know an important fact. I was born without that gene. That gene that most girls have that makes them read fashion magazines and create fashion icons and have a desire to keep up with current trends and wear, to some degree, what everyone else is wearing. I would much prefer to just wear what I want.

Now, here I am. A functioning adult. I don't wear make-up. I sometimes brush my hair at work. My only hair bobby is not a barrette or a scrunchie or a banana clip, but sunglasses. I have clothes, some of them are nice. I have more dress pants than jeans, I suppose that's a good thing. The problem is that I'm not sure that I like any of it. There are a few outfits that I feel I look nice in. Some that I think are my color. Some that are comfortable. But, I don't know if there are any that are "me." I have decided, a long, long time ago, that I just want to dress the way I want to dress and to hell with what Cosmo says I should wear. The only problem is that I have no idea what I like.

I watch a lot of What Not to Wear. I have learned a bit of what I shouldn't wear. I need pants that fall straight from my hips, jeans with a medium waist. Layers. Etc, etc. But, I still don't know what I like. The other night, when we were watching, they asked the person to choose a style icon. An actress or singer or even character whose style they liked.

Then, a few days later, I found this. I guess I get it. There are celebrities whose clothes I always like. Stevie Nicks comes to mind. I was always partial to Tara from Buffy. That's all I've got. And frankly, I think that I'd look like an idiot in their clothes.

On What Not to Wear, they ensure me every Saturday night, that olive green is a neutral. And you can wear anything with it. So today, I put on dark olive green capris and a red t-shirt and walked around feeling like a Christmas tree all day.

I don't know what to do with myself. With my wardrobe. With my hair. I haven't had a haircut I liked in ten years. I never wear make-up and when I try, I feel like a look a little ridiculous. The Husband confirms that when he tells me that he doesn't like it when I wear make-up, because I don't look like me.

I watch What Not to Wear because I want them to teach me what I should do about this. I used to read fashion magazines, hoping to get a handle on what's in and what's out. At the end of the day, though, I still try on practically everything in the store. I still hate most of the clothes that I walk out with. I still don't know what color eye shadow I should wear. Or what color lipstick won't make me look like a well-fed vampire. I don't know how to wear my hair, or how short to cut it or if I should straighten it.

And I don't know how to learn.

Finally, the Request:

I am smart enough to not ask you all to tell me how to dress. In the first place, you don't all know me. You don't know my body or what looks good on me. There's that lovely picture of me over there, but it's been there so long before it's so much prettier than I normally am that I can't replace it. Ever, possibly.

But what I can ask you is what connection you have to the fashion world. Do you take your cues from fashion icons, and if so, who? Do you read the magazines? Do you watch the shows? Do you obsess or do you just throw on what you like? If you just wear what you like, how do you keep out of a rut? Most importantly, how do people, you, anyone you know, manage to look fabulous and effortless at the same time?