Like Dorothy, sometimes what you’re looking for is in your own backyard.  Here are some things you can do right now to convert your outdated pieces into updated looks: 

Outdated:  Prairie skirts
Update:  Prairie skirt pulled up to the bust and worn as a strapless short babydoll dress or long tunic.  We’re not kidding.  Try it. If anyone asks, “Why is your skirt shoved up under your armpits?” Just look at them witheringly and say “Um, Lanvin’s groundbreaking 2006 Fall Collection?  Maybe you’ve heard of it?”

Outdated:  Baby tees and cropped tops
Update:  Layer over a long top, tunic, or or your new babydoll dress (see above)

Outdated:  Plain knee-length shift or sheath dress
Update:  Belt under the bust, and/or add leggings or jeans, and/or layer over long-or short-sleeved tee.  If this sounds weird, just wait--it’s already a big look in New York City and is definitely headed South.

Outdated:  Long, fitted pencil skirt
Update:  Hike up to high waist and “paper bag” with a fat belt to make a tulip-style skirt

Outdated:  Hip-slung chain-link beaded belt
Update:  Wear as long necklace.  (Don’t worry if the beads or links aren’t evenly spaced-- the asymmetrical look is the way to go)

Outdated:  Plain long tanks and tees
Update:  Layer under cropped sweaters, or jacket and/or belt at high waist

Outdated:  Cashmere Sweater Set
Update:  Split the set and wear the cardigan over a long-sleeved tee or white blouse with the sweater sleeves pushed up above your elbows. (The puffier the blouse sleeves, the better—the balloon- sleeve look is hot right now). Wear the shell as a sweater vest over a blouse or tee, and add an interesting necklace, like your old chain belt (see above).

Outdated:  Capri, boot cut, or flared pants
Update:  Have them cropped and cuffed at knee to wear as Bermudas, or if they’re fuller, crop below knee to wear as gauchos.  Or, if you or your tailor are up to it, convert those bootlegs into skinny legs.  You’ll have to redo the side seams from the knee down, but for high-end jeans, it’s a lot cheaper than buying new ones. 

Outdated:  Unstructured jacket
Update:  Shorten the sleeves to elbow length and crop the bottom.  Wear over long-sleeved blouse or tee.

Don’t be afraid to experiment--you might find that you have a lot more wearable things in your closet than you thought!