Now, that said: Nothing screams insecurity like someone who's in clothes they don't believe they can pull off. Hobbling down the street in sky-high heels is not a sexy look. Aim for confidence over comfort. Meaning: Yes, you should be able to walk without support, but you also want to wear clothes that flatter you and that help you look and feel more confident. It goes without saying that you shouldn't invest in clothes that do not fit or cause you serious pain.
If you don't feel sexy in fitted clothes because you're sensitive about your belly, then you wear a top that flatters your midsection while playing up your rack, if that's one of your assets. Great lipstick if you've got full, sensual lips. I mean, this is basic fashion advice right? Play up what works, play down what doesn't. It doesn't matter if you wear kitten heels or stilettos--it's whatever puts a little swing in your hips and makes you feel like sex in a bottle.
Take this quick test when you look at an outfit:
-- Could I just as easily hang out on my bed reading magazines in this? (Change out of it immediately.)
-- Would I wear this very same thing to a baby shower or a work meeting? (If yes, it's probably a little dull.)
-- If this outfit could speak, what would it say? "I'm on my way to a 6-month cleaning" or would it simply purrr or perhaps even growl. Go with that one.
-- Did I wear these shoes to clean the garage? Would they be aptly described as "practical?" Change them. Shoes are the punctuation to your outfit. They should say something, and it shouldn't be, "I wore these for five hours in line for the iPhone 5."
Is This Really Me?
It's clear what you're really getting at here, and it's not so much what looks good on you (because I think you already know, and if not, go shopping with an honest and stylish friend). You're really asking, "If I make an effort, am I not being true to who I am?"
What you're assuming is that there's only one "true" you. That the "real" you is in your underwear watching Honey Boo Boo Child, or in work pants and a sensible button down eating a pita pocket. Well, tonight the "real" you is going to wear a silky top and a skirt, and slurp down oysters.
You aren't choosing whether to be you or not to be you when you get dressed to impress. The idea is, how do I broadcast my best self. You don't become someone else by sliding on some heels. You simply unmask another side of you.
Related: 6 Things Women Do That Scare Men Off