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Utility Jacket
Wear it on its own, or slip it under a parka on colder days for a cool layered look.
Neutral Ankle Boot
A goes-with-everything, Kate Bosworth-y staple.
Dark Jeans
Swap your summery white ones out for these.
Cable-Knit Sweater
Use it to offset an ultra-girly circle skirt.
Leather Jacket
Weekend default.
Plaid Pants
Perfect with a fisherman sweater and tomboy-ish loafers.
Cashmere Sweater
For the ultimate slouchy fit, buy it a size larger than normal.
Statement Jacket
Cool enough to turn a basic tank top into an interesting outfit, and thin enough to layer underneath a coat without being uncomfortable.
Leather Skirt
Its texture makes it dressier than a simple black miniskirt.
Trench Coat
Pick one with cool details like this, so it's versatile but memorable, too.
Riding Boots
They'll give your basics a bit of preppy charm.
Plaid Shirt
Pair it with ripped jeans and bedhead, or go sleek and Miranda Kerr-y with leather pants and a pointy-toe heel.
Corduroys
It's pants weather most of the time in the fall, so you'll want something to  break up your jeans-all-day-every-day routine.
Thick Black Scarf
The chunkier, the better.
Turtleneck
They're having a bit of a renaissance right now.
Black Tights
Stock up on them early in the season and you'll never have to deal with the "all my tights have runs in them but I really need to wear them with this outfit" panic.
Leather Gloves
Get a bright color so you won't forget them on your work desk or leave them behind on a restaurant banquette.
Dressy Ankle Boots
With jeans or with dresses, they'll be your most versatile fall shoe.
Striped Cardigan
Like the striped t-shirt you lived in all summer, but cozier.
Beanie
Gives everything a bit of swagger.
Sweater Dress
Cozy, but polished.