Jean Challenge

So like every other girl in high school I am getting pumped for fall (and therefore school) not for the leafs changing (which I am!) But back to school shopping. Do I get more waist skirts, a trend that is bombarding my closet, do I go for the cutout look, or lace or leather? Last year I made the effort to not wear my usual jeans and hoodie, which I succeeded, in the not wearing hoodies often part.
However, this year, I call a new challenge. I only can wear jeans 3-4 times a week, while you might think this is an easy challenge, but a girl thats collected about 15 pairs of jeans and find them gods answers to many outfits. This wouldn't even be this bad if I didn't have the habit of getting mostly dark wash plain jeans, so when i do start going back to school shopping (after I finish my 10 pounds weight loss challenge of coarse) I want to get some unique pairs...

(forever 21)
or most likely something like this (something i already have similar in my closet)

(forever 21)

I was thinking on those off days when I don't done my precious jeans I would wear a simple dress (like that adorable black and pink h&m polka dot dress i got a week or so ago) or maybe a skirt. The real challenge comes when new york state winter sets in... Of coarse leggings can go under the dress or skirt when that time comes. I also want to give trousers a shot, maybe i can find a pair I like that my mother or grandmother wouldn't wear.