I'm 27 and very picky. In the old days I was a punk rocker and had a uniform that I'd don everyday - usually in all blacks and grays. I fell in love with color when I was pregnant and I abandoned total-masculinity. Still, my aesthetic has a bit of an edge. I despise wearing boring clothing.
I like clothes to be warm, comfortable, AND pretty. A tough order, and not cheap UNLESS I do it right.
I do like feeling sexy, but I can't wear anything that I have to pay attention to. Short skirts, for example, drive me bonkers because I'm a klutz and a tomboy. I've got to be able to move, play, and get dirty. "Girl clothes" just aren't made for this. I prefer an understated sex appeal: Lines that work for my body type, long and lean trousers with a form fitting top; a tighter skirt with knee length hem and a slouchy sweater; shorts with boots and a long sleeve button up, etc.
All sweaters are bought on sale or used. I will not spend more than twenty dollars on a sweater. Preferably much less. I only buy cotton, wool, cashmere, and silk sweaters with a timeless cut. I still have clothes from when I was 16 and I plan on having clothes in my closet for a couple decades. This is what my mom does. Wait twenty years and they are guaranteed to come back in.
I patch clothes and replace buttons.
I don't get clothes very often. I'd rather spend twice as much twice less often than get junk that is going to fall apart.
Undies and bras I get at target or Ross. I have small boobs and a thin frame so it's not hard to find comfy cheap bras. Ditto camisoles, undershirts, and tanks.
I geek out on clothes. I look through blogs and magazines and find inspiration in the natural world. I spend time picking out my "costume" for the day. Wearing nice clothing that feel good (and are functional) just makes me feel happier. I enjoy mixing texture and color.
I usually cover my shoulders and back, or will put a button up or cardigan over a tank. Just my preference. I have a few girlfriends who rock shorter hemlines and they look gorgeous. I'm just more comfortable when I'm more covered. Beach trips I throw this rule right on out the window.
I like masculine lines. I only wear leather shoes and belts. I like leather.
The trick for me is to think of developing a closet like a treasure hunt. I collect one piece at a time. No overhauls or total make overs around here. Just a slow collection and shift.
My favorite brands can be found cheap WHEN used. I just found this shop that has used Anne Taylor LOFT, J. Jill, J Crew, 7 for all mankind, banana republic, Barney's, etc. I won't spend more than 20 dollars on anything other than boots (once a year or once ever two years I will spend a pretty penny on boots).