sassy and karma do not go together
First of all, stop being self-defeating.
Get copies of More and O (Oprah's mag) to start with. Check out their suggestions for women in the 30-50 year old range. See if it's something you'd like to try, they cut out picture and make yourself a style book. A regular notebook will do.
Take it to Kohls, since you feel comfortable there, and look for things that fall into your desired range. Make sure you wear (or bring) the shoes and even undergarments you will wear with the clothes.
Don't be overly critical. If you start to feel that way, buy the stuff, take it home and try it on in your comfort zone. Kohls will take anything back, even if the tags are completely missing.
After you feel comfortable looking in Kohls, branch out to other stores. Start looking at other magazines, but be aware, most cater to a much younger crowd.
As far as having someone shop for you, there are 'personal shoppers'. I think Macys has them, so the other large department stores probably do too. You may even be able to find a freelancer. That would be ideal. Not beholden to the store.
This is the FUN part of losing weight, so have fun!