Outfit Insecurity

This is my outfit anxiety face.
I'm pretty particular about how I present myself. I mean, of course I am; most people are. For some people, it's pretty obvious - you can tell that they make an effort to be stylish, to be well dressed and well groomed. For other people, it's a deliberate lack of care that they're trying to evoke. For every person that you know who loves to get dressed up and put on that perfectly fitted suit, or just the right shade of lipstick, you probably know at least one person who can't bear to look too fancy, or like they care too much about their appearance. It's all about how we want people to perceive us. I don't know too many people who legitimately don't care about what they wear.
I mentioned yesterday that Friday was the one year anniversary of my first date with Brian, so of course we had to figure out something to do. He left me in charge of planning, so we went to see a really awesome show called The Boxer, at the Athenaeum Theatre. It's a small theater, and they do some interesting productions. This one was like a silent film that was translated onto the stage. There was a pianist playing the backing track, the actors had the sort of expressive faces you find in movies from the teens and 20s, and they had this great trick with the lights that made everything look sepia toned. We both absolutely loved the show, and our dinner afterward was decadent and delicious.
The one issue that I had was that I really didn't like what I was wearing. I'd gotten dressed in a hurry that morning, so I was just wearing my work skirt, which is navy, polyester, and above the knee length, and a navy blue and white striped top. It's not that I hate the pieces individually - I just felt so corporate, so not-myself. I had a little pink and blue striped hat that I was wearing with it for a little while, just to give me that vintage feeling that I like, but I took it off when Brian said it made me look like a Dutch dairy girl at a business lunch.
I felt uncomfortable enough in the outfit that I even considered buying a new one at forever21 before I met up with him, although I decided against that in the interest of keeping my finances in order. It's so strange how something like a skirt that's just a little shorter than I would normally like, or a boring but serviceable top, can make me feel like an alien in my own skin.
Printed dress, printed head scarf, printed shoes, snake brooch slithering up my shoulder strap: totally comfortable.
Comfortable enough to hang out in an alley taking pics, anyway.
The vintage aesthetic has come to be a huge part of how I see myself. I can wear an outfit that's loud and attention getting, or over the top feminine, or a petticoat so big it takes up two seats on the train, and not twitch. Put me in business casual outside of work, and I turn into a bundle of twitches, tugging at my skirt and rifling through my purse for a scarf or a pair of button earrings, just to make me feel more like myself.
I'm sure it's not uncommon to have an experience like that. You know how it is - everyone around you is like "you look fine," but in your head you're just itching to rip your clothes off and put something else on. When was the last time you experienced something like this? Or are you that rare bird that generally feels pretty comfortable with what she's wearing, even if it isn't quite typical for you?