This was inspired by this girl who worked at J.Crew and my outfit for today..
 
Now in NorCal, it's still not hot enough to wear shorts and crop tops. A very basic sweater, you should be able to find one in many stores, probably not of the same shade or pattern. (American Apparel, J.Crew, H&M) Some printed jeans or leggings, since they're what's hot. (H&M, American Apparel) A simple, plain, loose-fitted tank, from you summer wardrobe. (Cotton On, H&M, J.Crew, Forever21) A plain scarf, infinity or not, to keep your neck out of the still-harsh wind. (H&M, J.Crew, Forever21, True Religion) A warm-toned bag, some printed bangles, necklace or not, if you want earring.. Now if the tone of your outfit is similar to this set's, pair it with a bright pair of pumps, or flats, if you love your feet. (NineWest, J.Crew)
 
For this look, it's best to have a high bun, maybe add some flowers or neutral-shaded accessories. Don't go overboard with makeup, simple eyeliner, mascara, and a warm-toned eyeshadow (please don't use blue) to give you a clean natural look. For a bolder look, change the shade of your lipstick. Always go with mattes for these looks. Orange, red, something perky to match your shoes.
 
Too bright and girly? Try wearing a darker cardigan or maybe an oversized button up shirt, with a leopard-printed scarf or something wild. Dark toned leggings or jeans, white tank, with a pair of red TOMs. No accessories. A high messy bun and winged eyeliner. My outfit today.

Oversized. OVERSIZED. Cardigans, sweaters, whatever. Infinity & Circle scarves. Boots with legwarmers underneath, or just a pair of warm colored pumps. The rich colors. God I love fall. Two outfits, somewhat similar parings.
 
Voicing my opinion: I think oversized knitwear and loose fitting tops look the best with a simple bun...

Flannel + jean shorts with a pair of combat boots and some "punkish accessories". Damn girl. Me gusta.

You know Hipster folks, trying to get the most expressive clothing for the lowest price. Sadly, Polyvore doesn't carry thrift store prices.
 
Here's a complete outfit for approximately $117 USD, not including tax. But if you just want the dress, shoes, and bag, its approximately $72 USD, not including tax.
 
Hairstyle could also be a side braid, or anything really. Pair it with a simple cardigan on a windy, or if you just want to hide your arms from the sun. Minnetonka ankle boots would also be a lovely match.
 
I actually checked all the prices and did the math, you're very welcome.