I've GOT to start dressing better

I was sitting on a friend's porch who lives in a nice neighborhood. As we were talking, a young woman walked by pushing a stroller. She was wearing a cute dress, hair pulled up in a chignon held in place with chopsticks, and suede fringe boots with a cool scarf wrapped elegantly around her neck. I said something to my friend about how mom's staying at home even dress better than me. She looked at me and said, "she's the nanny".

Now I'm not saying nannies should not look good (I have been one) or SAHMs. It is just a little sad that someone like myself making a living as a graphic designer is shopping at Target, and even thinking, 'Is it okay to wear the sleepwear sweat outfit as regular clothes? It doesn't LOOK like sleepwear." Someone please help me. Sign me up for "What not to Wear", please! Only problem is that my outfits are more blah then completely unflattering or outdated which probably makes for a better show.