Does it fit? Is it attractive? Is it timeless? Does it make me look and feel my best?

I certainly don't like deciding.
Remember yesterday, when I admitted to liking "more is more" when it comes to decorating?
It seems like I like that socially as well. Meaning, it seems like the more boyfriends, the better. Usually.
I know I'm not supposed to admit to this. When my cousin Garret talks about all his lady friends, the worst people think is he's a player. Mostly, he gets high-fives (even from me, and you know I'm a champion of and for women). But there is the very difficult position I've put myself in by being honest-- I can't decide how to cut most of the boys out, so I just rotate 'em. And that makes me sound trampy, though I certainly am not. A tease? Perhaps. A flirt? Unfortunately yes. But I'm no tart.
Still, every time I think about paring down, I'm seized by fear. What if I need that one later on? It's like when you clean out your closet and take clothes to a local charity. Some things are easy to cast off; sometimes they're even new-- something you bought on impulse but regretted as soon as you got it home and were too lazy to return it. Or worse, it was on sale, so you can't return it. Like an ill-fitting dress taking up room in your closet and still sporting the price tags, there are boys in my life who take up space, but periodic spring cleaning is enough to offer them to the less fortunate and more lonely.
However, there are always those "heirloom" pieces you think you've gotta hang onto. I tend to be very sentimental when it comes to clothing. For ages, I kept all these T-shirts I don't wear. They had catchy, irreverent phrases or represented some era of my life or another. I hated the way they took up space in my bottom drawer (I hardly wear logo-shirts at all anymore), and I thought maybe someday I'd turn them into something better, like a quilt. When I finally threw them away, I was surprised that I didn't miss them at all. In fact, I didn't even think about them until just now. There are men like that in my life. I know they're not a good fit, but I keep them around because there's something a bit likable about them. They're begging to be worn, acknowledged, and shown off, but they just don't get a chance at the light of day. Like my high school theatre troupe shirts, I care too much about them to use them for manual labor, but they just gather dust and take up space. When I do finally get rid of them, I forget I even had them.
Then again, in my closet and in my chest of drawers, there are the pieces I've simply worn out. I'm hard on clothing and I'm hard on my men. I once had this Matchbox 20 shirt. It wasn't the typical hokey concert T-shirt. It was simple and stylish and a great color for me. It was soft and I loved the way it felt and made me feel. I wore it in Poland my first summer. I wore it in college. I wore it again in Poland, but the second summer only as part of my pjs, because it was kind of hole-y (holy?) and faded. But I loved it best. I wore it for the two years I worked in independent film. I wore it when I lived with my parents and when I moved into my own house. Along with the vintage comic-strip pajama pants, I lived in and for this shirt. But one day not so long ago, I had to face the facts-- those jimmy jams were no longer appropriate. They had too many holes in too many important places. They were comfortable, but I needed to get rid of them. I bit the bullet. I threw them out. I got new pjs. I miss them still.
There are all kinds of things in my closet, just like there are boys in my rotation. Both are a little too packed for comfort, even though I love most of my clothes, and even most of my boys. Sometimes, you've just gotta figure out what you can live without.
*Stuff that needs major repair, but is still great: Sometimes it's easier to throw something out than hem up the slacks that drag because you're too short, sew on the button where faulty manufacturing or your hard wear has left a gap in the clothes, or patch the hole in your jeans so you don't look sloppy or exposed. Some pieces are worth fixing, but many are not.
*Clothes that no longer fit: This type of clothing can be particularly frustrating. If you're lucky, you've lost some pudge, but you find your new lifestyle and body make your clothing appear overwhelming and oppressive. It drowns you. On days when you feel bloated or chubby, it's a shame that those perfect shorts look a little too tight. They're your favorites, and the ones you'd choose again and again for eternity because there's an element of perfection to them. They were made for you, you think. Maybe you've outgrown them or maybe the universe is messing with you because even though you look and feel better than you have in ages, they still don't fit right. You want them, but they don't seem to want you.
*Matchy-Matchy Outfits Your Friends Have: My friends tend to have similar taste in clothes. Sometimes we shop together. And some pieces are so great, it doesn't matter if the girl is typically into a different style of clothing-- if it's amazing, she wants it. So while it's awesome to sometimes stage dress-alike days, it can cause a little bit of agony when you've got one piece that's the perfect fit and super flattering on all the women you know, but the store only has one available. I've always been about having my own identity, so my first inclination is to just give in and let others do the matching. If there's a scarcity problem, I know I'll be extra tempted to buy due to the off-limits or high-demand nature of the product, but no one wants to be the girl with the great wardrobe and no friends. It's hard to know if there's ever a time when couture is worth hurt feelings.
Anyway, my closet is full, and I need to get rid of some stuff. I like a lot of it, though. There's a shirt I keep threatening to throw out, but it just needs some fixing up. OK, a LOT of fixing up. But it hugs my body in the right places and though it wasn't what I expected, I am strongly attached to it. I hate to get rid of it.
I've got this trendy jacket right now. I think other people like it way more than I do, so I should just pass it on, but it's new and manages to hold my attention. Still, it might just be taking up precious space.
There's a pair of jeans I wasn't originally impressed with, but as I've tried them on a few times and worn them in, I've discovered they're pretty much perfect. But I can't find them when I look for them. They show up when I've got other things to wear. When they'd be perfect for an evening out, it's like they've run away because they know I like them too much. These jeans feel classic and edgy all at once, and like they'd be in style forever, but they're just not there when I need them.
And there are several shirts in my closet that match stuff friends have bought-- intentionally or otherwise. What can I say? I hang out with girls known for their good taste. Sometimes these are the pieces I like the very most, but I feel too intimidated to wear because they look better on the other girls, or because I'm afraid I'm stealing someone else's outfit thunder. It seems like such a shame to throw them out, but just wearing them around the house and away from my friends is not a solution. They just hang in my closet, and I can't tell if I really need or want them or not.
And let's not forget about my old stand-by pajamas. I sent this pair to Poland, and ended up reunited with them in Utah. I couldn't be away from them, even though I didn't move just for a pair of silly pjs. But they were appealing. I used to think they were too beautiful to wear, and just kept them on a high shelf. But when I'd put them on, I loved them. Now I know they're just jimmy jams, and there are a lot of others in my third drawer. They're made from organic cotton, and when I wear them, my dreams seem more pleasant, vivid and empowering. Sometimes when I wear them and look in the mirror, they're not as forgiving as I'd like. I can see my flaws more clearly when I wear them and parade around. But they're still comfortable. They managed to end up in Nicaragua for a month. I finally feel worthy of them, but like my jeans, they're just not around.
Anyway, I'll be cleaning out the closet again soon. Anything uncomfortable is going to charity. If it doesn't make me feel great and confident, say goodbye. The cheap impulse buys are a sunk cost, and they can be packed off to those whose closets are so bare they'd be thrilled with anything. The timeless, the unique, the stuff I try to be better for to look better in-- they can all stay. I wish I could find the right outfit, though. I'm tired of not dressing appropriately.