I'm trying to convince myself that it's okay to spend money.

There are certain areas where I have no problem with it, mostly when it comes to buying books. I've started buying CDs again, though I'm trying to get used stuff when I can. I even bought some new video games a couple of weeks ago. Where I have trouble is when it comes to buying clothes. I have to talk myself into spending more than about $20 on a single item. I'll stand in the dressing room, going through what I could wear it with, question if I actually need it, looking for fitting problems that will make me put it back on the rack.

This wasn't a problem when I was younger, probably because I was using my parents' money. Actually, that's not quite true, since this problem first manifested while they were still paying my bills. I guess after going through my closet so many times, after getting rid of so many barely worn clothes, I started to feel guilty. I started to analyze my purchases more, to reconsider things.

In many ways, this is a good thing. Most of the clothes that I have now are items I wear on a fairly regular basis, except for the fancier dresses and such. (On that note - someone, please invite me to a swanky cocktail party. I have the dress, but no place to wear it.) However, I'm also in a bit of a rut. I'm afraid to count and see how many grey and black t-shirts I have. I'm trying to branch out slowly - for instance, I've gotten a few shirts that are a bit nicer and aren't grey, black, or navy. But each purchase is a battle for me, especially if it involves colors. Will I actually wear a purple blouson tee? (Answer: Yes. But hesitantly.) Will I wear something with ruffles or flounces? (Answer: So far, no.)

The battle becomes much more involved when the price increases. It's not like I'm shopping in designer boutiques or anything, either. (Confession: I am terrified of going into nice, non-chain clothing stores. I stare at the windows wistfully and then flee.) I'm talking about J. Crew or Banana Republic. And it's not like I'm buying trendy things that can only be worn for a season. The black eyelet a-line skirt I wore today? I think I've had it since 8th or 9th grade. I like simple, classic stuff.

In theory, this sort of clothing is what one SHOULD spend a bit more money on. They're the wardrobe staples, the investment pieces. But I have so much trouble doing it. I'm an adult now. (Supposedly). While I can get away with wearing jeans and a t-shirt to work every day, I feel like I should be stepping it up a notch. I want to dress nicer. I pet soft sweaters, sigh over lovely pinstriped skirts. But as soon as I see the price tag, I freak out a little.

Today I made progress. I went to J. Crew to look at a dress that was on sale online. They didn't have it, but I tried on some other stuff, including a dark grey knit dress and a navy blue a-line skirt, which I bought. Of course, I'm still not 100% convinced that I should have bought them. That's why the tags are still on them. If they past the roommate test, they'll get moved into the closet. Then I'll force myself to wear them. And I'll continue my baby steps toward dressing more like an adult. Admittedly, these steps are being taken in cheap flip-flops, but that's an issue to deal with another day.