Can you please fix my extremely epic fashion failure?

[SomewhereIBelongt]m1]

I've got no clue as to how to dress myself nicely or fashionably. I wear:
~sweatpants, track pants, basketball shorts, capris
~t-shirts, thin long-sleeved shirts, hoodies
~jacket in the winter
~basketball shoes when there is no snow (old ones for outdoor, new ones for indoor; the old ones are 5 yrs old)
~plain black boots to keep the snow/cold out in the winter

I am completely averted to wearing:
~makeup
~any item costing over $15 (CND)
~any footwear that reveals any part of my foot (I hate feet)
~anything that will make me overheat in the winter

I hate shopping and trying stuff on as well.

BUT! I found a skirt like this a few months ago at H&M for $15
http://www.styleblab.com/wp-content/uploads/2007/09/verawangskirt2.JPG

I like it. Will I have to wear tights with it?

I don't wear open toed shoes. I'll need the right kind of boots to wear with it. Boots where the primary goal is not to insulate your feet from the elements, but rather to look nice and still be comfortable to wear in warm weather. It has to be cheap. I don't shop at skanky fake teenybopper stores.

Any suggestions?
lol are leggings seriously the same as tights? If so, forget it. lol.

 

[sassynightcrawlerchick]

ebay

 

[ashley39056]

You don't have to wear leggings but they could definitely add color if you chose like a bright color. You could also wear bright flats that match the leggings or black flats and a shirt to match the leggings would probably be better. And also you might want to look at stores like Wet Seal, Forever21, Rue21, Charlotte Russe, and other stores like that! Hope this helps!