STYLETHREAD -- LET'S TALK SHOP!

WOW, 5K.  Lucky!! Haha, its hard to recommend things simply because you have so much money to spend, you could buy anything you want! (well...within reason)  If it was me, I would spend about $2500 on nice or pricey pieces - i consider everything i listed below as "nice" (except the VS pumps) because of the price (not saying something has to be expensive to be nice, but you know what i mean- the boutiquey things that you develop a crush on and make a dent in your budget), then about $500 on carefully thought out cheaper filler pieces (don't go crazy or you won't wear the things, but maybe go to H & M and the Gap and get some layering tops or blazers from AE or something), and then save the $2000 for later in the season, after you reassess what you need.  If you spend it all at once, guaranteed you'll want something new in two months.

For flats, I recommend:

$125 at J. Crew, haven't seen these on ebay, tried the 9 (size down), and they are soo cute and comfy

I'm also in love with these Burberry flats in black, but they come in many colors- they are $275 (desperately seeking sale) and pretty comfy yet unique

For jeans, i would get a pair of skinny jeans and a nice pair of trouser jeans, plus maybe more of a casual jean- I think the October Teen Vogue has some recs, I'm not sure what city you're in, but i would go to some stores (Tsubsi, Earnest Sewn, maybe some boutiques) and find a really great fitting pair of straight jeans, they will probably be pricey but will look great with looser tops and to wear at night.

I saw the girl at J. crew wearing just the regular hip slung jeans (i think they were $88) and they looked great on her.  great for day.

http://www.jcrew.com/catalog/product.jhtml?id=prod69872691&catId=cat74858

I like these Joe's trouser jeans, not as dressy as some, but very cute:

http://www.anthropologie.com/jump.jsp?itemID=6302&itemType=PRODUCT&iSubCat=897&iMainCat=896

For sweaters, i have this Inhabit cashmere one and i adore it, pricey at $289 but retail is near $500, only S and L left, so if you are my size or slimmer (4), the S should work, but L could work in a slouchy way:

http://www.bluefly.com/pages/products/detail.jsp?PRODUCT%3C%3Eprd_id=2010554981&FOLDER%3C%3Efolder_id=2006562079&N=933&Ne=500000&Nu=Product+ID&Ntk=all&Ntt=inhabit&Ntx=mode+matchallpartial

I also really like this one, $140:

http://www.anoseforclothes.com/cc/store/cc_viewItem.asp?idProduct=1322

I also love these snakeskin heels for night, $50 Victorias Secret

http://www2.victoriassecret.com/commerce/application/prodDisplay/?namespace=productDisplay&origin=onlineProductDisplay.jsp&event=display&prnbr=SE-189372&page=5&cgname=OSSHUDYSZZZ&rfnbr=2424

i prefer the color of snakeskin on the left but with a back like a regular pump, lower heel which i always prefer if i'm going to be walking even a little

I also like this bag, though i acknowledge its too pricey at $400, its pretty in person:

http://www.anthropologie.com/jump.jsp?itemID=8121&itemType=PRODUCT&iSubCat=328&iMainCat=325

I've seen this Ella moss hoodie in red at Anthropologie- its pretty cute and lightweight- not worth $106 maybe, but you could try to find a code:

http://www.goclothing.com/womens-ella-bohoody-black.html

it would be good with a tank for lightweight, and with a longsleeve shirt to be warmer, the knit is loose

If you are looking for cool jewelry- PM Jlear (stylethread member)- she sent me a long list of things she has for sale and they are awesome!  You could get 4 or 5 awesome pieces, easily.

I'm also looking at black pearl studs and I have ones similar to these- and they are very cute, different yet subtle- and only $88- mine were $180!! :

http://www.reformjewelry.com/shop/jewelry/octopus/oct-ets1.html