I have been holding on to items in my closet that I haven't worn in over 4 or 5 years. I have some sort of emotional attachment to things, I convince myself I'm going to fit in the same clothes I wore back in high school. I'm not sure if I can get away with tight fitting sweaters that show of my belly anymore (damn my obsession with Britney Spears!)
About a year ago I starting pulling things I absolutely could not see myself wearing out in public again. If I knew it was no longer age appropriate I threw it in a pile. I then started pulling things I knew I didn't feel comfortable in anymore. If you have to suck in your stomach for it to look decent, toss it. I may start the night off with a flat stomach, but a drink or two later I can feel bloated, not to mention after appetizers and dinner!
I wish It were easier for me to just get rid off everything all at once, but I have to slowly psych myself that its okay to let go of the past. I ended up filling 4 large shopping bags of clothing to donate. Now my wardrobe feels much more functional than before, it takes me half the time to get ready and I don't run into an old top and feel bad about not being able to fit into it.
The best way to approach my spring closet cleaning is by asking myself "would I buy this today?" If I have to think about it or if I hesitate, I'm going to throw it in a pile. Then I'm going to take everything thats left and find a really good tailor, so I can finally wear all those pants and great blazers I have been dying to wear.
And this is how I will feel getting dressed everyday from now on.