In a "Private School" Bind

So fall has officially begun and I'm in a pickle. I've always been to private school and so we had uniforms. I haven't had to have a real, functionally fall wardrobe for my entire life. I'm extremely unsure about what to buy for fall. There are a few things that I'd like to buy:

1. Shirt dress (my #1):

Vineyard Vines:

or Lilly:

2. I know I'm going to need khakis. I have them from American Eagle that I wore to school last year but I desperately need to let the hem down. That won't fly in college.

3. Corduroy skirts. I have a pink vineyard vines one, but I'd like one in khaki and navy blue (or maybe black?). Polo + Cable Knit + tights = fall outfit. I'd love to wear that!

3. Sweaters. I have several cable knits and Lillys but I always feel like I could use more. I need a black cable knit and I've seen 2 from forever21 with adorable bows that I covet. One's like camel colored, LOVE IT!

4. Trench coat. There's a traditional one from Old Navy that I LOVE. I have a grey wool pea coat, a bright pink car coat, and a cream Lilly quilted jacket so I have those bases covered. For the really cold days, I have a black North Face fleece (like the rest of the world's population of college students) and a pink parka that I can zip it into.

6. Jeans. I don't need more jeans. I have 3 pairs alone here with me. I may throw in my 4th pair that are super worn out (from wear, not by design) as junky ones.

7. Comfortable flats. I have a few pairs of flats that I love but Nordstroms has 3 pairs that I really want, but obviously won't actually buy all of them (if any, because then again I am a cheap college student):

These are my favorite of the 3. Pearls on flats? It can't get much better!

I've wanted Tory Burch Revas for awhile, but at their price tag, I may have to wait until Christmas or when I start working again over break.

Adorable, fabulous with jeans! Love the patent leather!

8. Boots. I've narrowed it down to 2 pairs from piperlime. These are one of the only purchases I know I'm going to buy. I think its necessary to have a pair of boots to go under jeans, or with jeans tucked in that AREN'T Uggs:

These are the front runners. I love them!

These are my other choice. They're darker brown, but I love the croc at the top!

I need fall shopping help desperately. If there is something that I didn't list please let me know! In SC, it gets just about as cold as it does in MD/PA it just takes longer to get that cold. I really appreciate any input!!

xxKatie

PS. THIS IS POST #100! Who knew a school assignment would go this far!