Do you dress 'Cool'? And if so what do you wear?

[NotGoodAtMakingFriends]

I can't afford to look expensive! My hair is too wavy and messy to look groomed! So maybe the cool look is for me?

Do you dress in a cool way or know someone who does, as I could really do with some help.

Get over to Pinterest and start looking at say celebs you think Dress to your taste, ignore red carpet shots and look for the daily paps.
Then you'll get ideas for outfits you like that you can again search Pinterest for, leading to blog posts etc.
I did this myself just last week. Found a look I liked, graphic tee, biker jacket. Put those words into Pinterest search, resulted in loads of similar outfits. Pinned them to a board and started recreating them with my wardrobe.