Dilemma

 So.... I have this dilemma. I only have a couple of pieces in my wardrobe that I find still cute. I think we have this terrible disease in my family that cute means new! haha Maybe not that direct, but there are certain clothes that loose their cuteness after a while. Most of my clothes are from high school. I don't want to buy a whole new wardrobe. I'm torn between:
1) Save up and buy good-quality "staples" (i.e. Find my own 'little black dress,' knock out pair of jeans)
2) Buy accessories and other cheaper versions of updating my wardrobe.

My real dilemma is I need to figure out is what I want! I don't believe I have my own style. I did in high school--loved the empire waist flowing shirts. Those I still find cute, and I will probably keep them, I just need to form outfits with them.
I think I'm ok with having this process take a couple (probably many, many) years. I understand we don't have money, but right now I really need a good pair of jeans and some final touches on my professional attire for the conference this month. The latter is on my urgent list. I am going to be meeting lots of people that I need to make a good impression on. Yikes!

I used to think I didn't know what was cute anymore, but I do. I attend a university every day! Aren't we like in the age group of fashionable? So, I don't think I can pull it off. And I want my own style, not to just look like everybody else. I really LOVE 1940s/1950s/and some 1960s (as you can see from this post). I have been desperately looking at websites and blogs to figure out what I like, what I think I can pull off, and what I think I can afford. Bah! So, maybe I'll update you all with my findings and ask for you opinions? That is if anybody reads this and posts comments! ;)