This probably won't happen but I do have a Lady Dior Cannage bag on my list because of a picture on TheSartorialist that featured a very chic French girl carrying one with a messy top knot, camel wrap coat, and black leggings while smoking a cigarette. It's only chic if you carry it with everything.
Military jacket to juxtapose with "dressy" outfits such as satin skirts--never with jeans.
Vintage Ungaro dress in the manner of Chloe Sevigny
An 80's dress or an 80's-inspired dress as seen above in the Altuzarra F/W 2009 collection. I believe Bebe is coming out with a silver lame ruched dress with one sleeve for $129. (Saw it in the August 2009 issue of American ELLE, page 276!)
Slim--but not skinny--white jeans. Tres chic. Any recommendations on brands and fits?
A few T by Alexander Wang tee-shirts
Vintage V-necked Lacoste sweaters in a variety of colors such as white, kelly green, maroon, navy, etc.
Leopard pony-fur flats. Sam Edelman makes one for $149. Saw it in the August 2009 issue of Vogue. (Supposedly Belgian Shoes, seen above, makes the most amazingly comfortable loafers. It's a WASP cult favorite but they're $310!)
Sperry Top-Siders or boating shoes. Rain-appropriate footwear