I was recently told by someone who knows me well that I appear, and have always appeared, as a total square.
This surprised me quite a bit, because I'm into a lot of "cool" things such as the music scene, indie publishing, drug culture, etc. I let my hair down and say ridiculous things, and tell loud stories, and dance. I wouldn't really mind looking like a square, except that I realize people have kind of never invited me to the really fun shit; I guess they assume I'm "not into that" because I look like a dang square.
To be honest I don't put a great deal of care in how I dress beyond basic hygiene and maintenance; I go to a very good stylist who cuts my long hair in a pretty tame, sideswept bang fashion, I have a few pairs of well-fitting jeans and khakis, and I basically wear a v-neck sweater or cardigan over a polo shirt every day. In my mind, I look something like this
, but I guess to everyone else I look like a total square. My goal is for kind of a twee sophisticate look.
So, how the heck do I hip it up so that other people besides the 3 who have known me for years don't just immediately assume I'm going to narc on them? For some background info, I work in a technical field where I can basically dress how I want, I'm in my mid 20s, I have a lot of nice shoes but mostly wear old ankle boots or chucks, I wear large dorky glasses, and don't want to spend a lot of time fussing every day.
I know that in general, you can't just immediately change your whole perceived attitude with online shopping, but links to specific products that I can buy that will make me appear a little less uptight would be appreciated. I'm not aiming to look super trendy, I just don't want to be glared at in dive bars anymore =(
(anon because drugs + embarassed)