I promise you that I will tell you soon all about my carpool, or at least those parts that are not strictly forbidden for me to tell. ("What is said in carpool stays in the car," I was told in my first week. Nonetheless, there are things to say.)
But for now, I'll tell you I've been troubled by your complaints about wearing a skirt. Darling, you have helped me so much, with your insistence that changing the system, not being frustrated or trying to behave differently, is the way to bring about desired life changes. Having a zillion nail clippers and emery boards in handy places, tucked into my desk drawer and my purse and upstairs and in the bathroom, that seems to have helped my fingernails get a little more tidy. I've changed my email system and that's working a lot better, too. So I'm an adherent, and when you tell me you can't wear the flirty red skirt that you bought and like in the mirror without being irritable and distracted, it's my turn to tell you to change the system. You need to have a system that makes it easy for you to look pretty and feel unencumbered and free in a variety of ways.
I have been working on building such a system. It takes intentional focus and discipline, because I am not very interested in clothing or accessories, and I don't have any particular flair or style, and dressing myself seems to be very hit or miss. But I am getting much better at it, and on the days I get it right I feel really terrific. For me, looking more grown up and cute has involved making some systematic changes, and paying attention (or, better, relying on the advice and attention of people who naturally care about this stuff) to things like clothes and shoes and handbags.
As far as I can figure it out, you're going to need a purse or a bag. You'll need to put your keys in it, and your swim pass and some money, and your cell phone. I also put a couple of pens in mine, because I always feel lost if I don't have a pen or two, and a lip gloss/chapstick that passes for makeup for me. If I carry my larger bag I also put my sunglasses in there, and sometimes the novel I'm reading. My little bag doesn't have much room for extras, but it's just enough. Why do you resist the idea of a bag?
You'll also need some cute shoes, with a little bit of a heel perhaps. These will make your extraordinary calf muscles look even more beautiful. I am finally convinced that it is possible for cute shoes to be comfortable, and I have five or six pairs of cute and playful and girly shoes that I am nearly as fluid in as my flipflops. I don't think you and I have discussed shoes, although I think we've touched on boots. Have you solved this problem yet, or is it part of the system you need to fix?
The skirts and dresses get easier once you have a bag. I have been relying on the Lucky Shopping Guide to teach me about clothing -- everything from what to look for in the fit and cut of something, to how many skirts a person should own, and of what sort. Then I talk to the ladies in the cute boutique I really like, and I throw myself on their mercy and pity. Really, how on earth would you wear something like this? They can explain why something works or doesn't -- they have words and they notice details for things I don't really even see -- and once they teach me I can start to see it too.
The days when I wear makeup, just a little, are also the days that I look more polished. I am trying to make that a habit, a swipe of powder, a little brown eyeliner and some brown mascara, then the chapstick/lip gloss. The items I need are inexpensive and I have them in three places: where I get dressed and put my contact lenses in, my desk drawer at work, and in my swim bag, so it's always easy to do it. As you explained it, changing the physical system to make good intentions easy to fulfill has a huge impact on my follow through.
The last frontier for me is jewelry, and I haven't figured that one out. Still the cheap black rubber wristwatch and some CVS $4.99 fake pearl earrings. I own a couple of necklaces and sometimes wear them, and lately I've begun to think about a bracelet. Still seems foreign and mysterious. Where are you on the jewelry question? Is there a system that is applicable here?