The mind is a hurdle to get past when losing weight

So I have lost 5 lbs. Which is a wonderful accomplishment given we just passed Thanksgiving. But yet I am not happy. My self esteem lacks so very badly. I have been watching "What Not to Wear" and I think I would be their biggest challenge. My graying dark brown hair always in a pony tail, bent glasses, crazy wild eyebrows, no make-up knowledge what so ever, and clothes I have worn for 10 + years. Most the time jeans and tank tops or baggy shirts. 

What can I say I was raised by a man and he didn't have the know how to teach me how to be feminine. Don't get me wrong my happiest memories are of playing catch and fishing with my dad. But now at 31 and as I am trying to get back to my pre-children weight I cant help but be envious of all their friends moms who always look stunning. I want to be that kind of mom.

I know we are our toughest judges but what I wouldn't give to be given the chance to wipe the slate clean and start over and be given the knowledge. But these things also cost money which is a luxury I do not have. What to do now? 

I must find a way to not only lose the weight but do something that will give me a new perspective of me...wash away all these negative feelings I get when I look in the mirror. This road to 135 is taking all kinds of twists and turns but I am hopeful although the road is still very long. 

Fingers crossed!