Everything has an expiration date, including clothes. Just because you can still fit into it, doesn't mean you should keep it around. Have you seen the commercial on TLC where the woman is like, "I can't believe this still fits" and she is wearing an awful yellow blazer with huge shoulder pads? Yeah, you shouldn't keep anything around for too long, unless it has sentimental value, they by all means keep it, but don't wear it outside. Cut it up and sow it into a pillow if you must. Every 6 months you should re-evaluate your closet and toss everything you haven't worn.

Some guidelines:

• It if it stretched out by any means, throw it out. Turtleneck with a neck a little too big? Toss it. Sleeves pulled down a little longer? Toss it. Lost a few pounds but your sweater hasn't? Toss it. Don't keep it around if it is stretched at all, it looks messy.
• Same thing goes with sweaters and pilling. The most common place for pilling is on the sleeves and since your arms are a pretty prominent part of your body, you don't want to be showing that off. You can try a sweater shaver, yes, they have those and they work! If it can't be solved with a sweater shaver, please toss it. Pilling is not pretty.
• After you wash jeans a number of times they tend to shrink a bit. One of the most common fashion faux-pas are pants that are way too short. Generally jeans should fall about a half inch from the ground, with or without heels. Anything where you can see the top of your shoes it a HUGE no-no. Nothing is worse than showing a little sock. Really, keep the socks covered with your pants. If you can't find any that fit, buy the next size up and have them tailored.
• Repeat this with me, "SAY NO TO SHOULDER PADS!!" Never, never, never, never do shoulder pads, ever, under any circumstances what so ever. NO SHOULDER PADS!!
• If you wore it in high school, you shouldn't be now. I am guilty of this. I have a pair of jeans that I wore in 8th grade, that I still wear sometimes. Let me defend myself. They are all broken in and so comfortable, but they are all ripped and torn. I only wear them inside and quick trips to the grocery store. I am such a hypocrite.
• I wear my shoes to death, like I get obsessed with a pair of shoes and I basically wear them until they die, but I know when it is time to toss them. If you must keep them, have they resoled or get the heel replaced, it is really an inexpensive way to keep your favorite shoes around. To increase the longevity of a pair of leather shoes, keep them polished and moisturized with leather cleaner. If you nick in a black shoe, try a sharpie marker to cover it up.