Are the skirts all different? Keep your receipt for them and the bag, you can take one with when shopping for shirts, so that you KNOW it will look good before you buy a top to go with it. When ever you want to match something, take it with.
I want to see the boots! I love boots, I only have 2 dressy pair... the other pairs are my "boy" boots, steel toe and one for hiking. LOL With how I dress, people are either not at all surprised I own chickens, giant dogs, and ride horses... or it's so girly/prissy they're like... "You know what a chicken is?".
I want to get a pair of western boots SO bad, but I haven't found a pair on sale that I LOVE yet. The trend for them was like a couple years ago, but I don't care, you can make it "timeless". Or wear it with skinny jeans or leggings and be "in".
Have you ever played with make-up? I have never felt more feminine as when I learned how to do a "smoky eye" and how to use all the silly little brushes. I went to a store that sells only make-up, and since I had never been there before, they made me up for free and gave me pointers. Before that, all I knew was blush, chapstick, and mascara. The art of eye shadow, using 3! colors, never knew how to do that. Then I signed up for the mineral make-up since it sits on my skin better, and they mail me everything I need every 3 months, but I have a low payment once a month to make it affordable. Totally avoids the shocking bill when you have to pay for everything at once. I've tried everything at the drugstore, and every brand at the department stores, the mineral stuff not sold in stores just lays so natural. Rimmel was cheap and a close second, but it clogged my pores.
A cute outfit and nice make-up means you can keep the tomboy pony tail and not fuss with your hair.