Esteem outfits

Do you ever have one of those days when you just don't feel good in your clothes? Your skirt is a little too short, top a little too snug, shoes are scuffed, sleeves too long? You pull and tug and rearrange, but always seem to be thinking about your clothes. You just don't feel good. Presentations don't go well. You snap at coworkers. I'm CONVINCED it's all about the outfit.

It's your low self esteem outfit. ((By the way, this pic of the ugly Duff sister, how could she possibly be smiling in this outfit?! It's horrid!!))

On the flip side, you may feel fantastic in a new suit - the one that is altered to fit, hemmed just the right length, not worn at the knees or too tight in the butt. You walk with your head held high and you look people in the eye. People treat you with just a little more respect - or so it seems. Thus, the high self esteem outfit.

I'm trying to talk myself into getting rid of my low self esteem clothes. But I have two problems:
1) I'm a bit of a packrat and constantly think, "oh, this will look so cute with (fill in blank here with something I either don't own or have no occasion to wear)"
2) I really love the idea of an overflowing closet. Tons of shoes, loads of sweaters and jeans, racks of tops, rows of suits.

Sadly though, most of those rows of clothes have been hanging there for months because they never come off the rack. All the clothes I do wear are thrown on the nightstand or on the bathroom counter. What a wreck. I know I would be much happier and more pulled together if I have just a few FANTASTIC outfits, and ditched all these half ass clothes that don't really fit or look too dated or have a hole in the pit or a stain on the sleeve. As of yet, I haven't been able to do this. But I'm tired of not feeling good in my clothes. Yeah, yeah, maybe it's more about the mind and the body underneath the clothes. I'll address that at some point too. But not today. One thing at a time. Today... wardrobe. But where to begin??