Building a Wardrobe on a budget

Have you ever looked in your closet packed  full of clothes but still didn't have anything to wear?  That is where I am right now.
Honestly, I do have clothes, but I don't have much that I feel good in.  I used to look in the mirror and think, yeah, I look good in this (I was also the perfect size 2 without any "extra to love" anywhere).  Anyways, after gaining 60lbs during pregnancy, losing 80lbs after pregnancy, and somehow gaining 10 back since Will turned 1 I no longer look in the mirror and feel good about what I see.  I have been getting kinda down and thinking, if I just loose 10, 15, 20 lbs it'll be better, if I just tone up it'll be better, etc...  I have come to a new conclusion; my post pregnancy figure is not the same shape as my pre pregnancy one, but it doesn't mean I don't look just as good.  It simply means I don't look as good in my pre pregnancy clothes and I need to build up a new wardrobe to flatter my new shape.  Now, how do I go about this on a fairly tight budget?

So far I have decided that one of the best ways to save money is to have a plan, so I have started with research - yes, that probably makes me a dork, but I have embraced that about myself too.  Anyways, back to the plan.  The way I figure it, I need just a few quality "key" pieces that are interchangable with everything else to get me started, then I can slowly add to my wardrobe over time from there.  ***Side note, when I say quality, I don't necessarily mean $$$.  Clothes can be inexpensive in price but still not cheap.  OK, back to the plan... again. 

Step 1.  Get 2-3 good fitting pairs of jeans.  This one is done, I used some Christmas exchanges and money, went to Old Navy, and bought myself 3 pair of jeans that actually fit.  I am very excited about it because I have been squeezing myself back into my old jeans thinking that because they buttoned and zipped they fit; I saw some pictures of myself from Christmas from all angles and let me just say, they did not fit.  Nothing about the jeans, or the top I had on come to think of it, was at all flattering and I'd like to apologize for all of the fashion rules I have broken over the past 20 months while squeezing into these things.  And, while I'm on the jeans topic I would like to give my opinion, it doesn't matter your age or clothing size, if your underwear (or lack there of) is showing while wearing your jeans, then it is not a flattering fit.

Step 2.  Get 2-3 solid color (possibly one striped) t-shirts that are not tight or short.  I don't mind curve hugging, but if you can see the seams in a persons bra that shirt is too tight.  I found some at Target the other day on sell for $7, I didn't buy them then, but they are now on my list.

Step 3.  Get a couple pair of nice dress slacks.  I wear scrubs to work every day, but when Chris and I go out on a date, go to church, or even if I just feel like dressing up a little bit I want to be able to.  I found one pair at Target on clearance for $11.98 this week that I snatched right off the rack.  They are cute, wider legged, grey dress pants that will go nicely with a silk camisole and cardigen, or even a more casual shirt.  I want to add a pair of black ones and maybe some kahkis as well for spring and summer.

Step 4.  Get 2-3 silky tops I can pair with jeans or dress pants and a couple of cardigans to wear over them.  I bought one of each at Target this week and am pretty excited about it.  It doesn't look like anything I have every worn before, but I'm a wife, a mom, a career girl and am almost 29 - I don't need to dress in the teenage ironic screen print t-shirts and the purposely ripped up jeans anymore. 

Step 5.  Buy some decent dress shoes.  One pair of open toed heels, one pair of black boots, and some sandles for the summer time.

I'm thinking I can buy a few pieces each month (I guess we know where my blow money is going for a while) and have a pretty stocked up wardrobe that fits me in no time.  Things that I'm doing to help me stay on my budget:

1.  Make a list.  Just like grocery shopping, I think having a list will help keep me on track.
2.  Go to places such as Ross, TJ Maxx, Stein Mart, Target, and even thrift stores such as Buffalo Exchange and for the younger crowd, Plato's Closet, and stear clear of Macy's, Nordstrom's, Dillards, etc... unless there are fantastic sells.
3.  Try things on.  This sounds like a no brainer, but I have a tendency to buy something because it looks awesome on the manequinn; duh, it may not look good on me.  If I try something on and don't like the way it looks I automatically save money because I'm not buying something I won't wear.

Any other tips for me?  Sorry if I got off track on this post.  I do feel scatter brained today, but this is what I've been thinking about lately.