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Devote an entire working day to the process. "This isn't something you can do in an hour," says D.C. stylist Ricky Summers. "If you really want to make progress, give it the time it needs."
Invite a friend. "A pal can bag clothes that don't work and put notes on items that need to go to the tailor," says Summers. The process will go faster, and you can return the favor.
Start with what's not working. "Be honest about why you haven't worn something," says Summers. "If you don't feel good in it, stop making excuses and get rid of it."
Don't be afraid to split a suit. If a jacket works, keep it and find pants or a skirt to go with it.
Make a pile for the tailor, who can answer questions about length and fit. "Long pants that make you look hippy might work better cropped," suggests Summers.
Don't toss something just because it's not the latest fashion. If something looks good on you, make it part of your signature style.
Take your rejects to a consignment shop or homeless shelter as soon as possible. "Otherwise you might get 'Shedder's Remorse,' and the stuff will creep back into your wardrobe,'" says Summers.
How to Shop
Don't go without a list. "It's the same as going to the grocery store," says Summers. "A list will keep you focused, so you won't wind up with bits and pieces that don't work together."
If you find a basic you really love, buy two.
Don't buy something because it's on sale. "The money you spend could be used toward the one piece that will really pull your outfits together," says Summers.
If you find fabulous evening wear, buy it. "If you happen upon that perfect black dress, eventually you'll have the occasion to wear it," says Summers. "Nothing's worse than buying something formal on deadline."
Get a variety of dark pants and skirts. "They will take you everywhere," says Summers. "I recommend a full-leg trouser, a dressy and casual pair, and a dark skirt."
The Five Pieces Every Woman Must Have
Great black shoes and black bag.
One fabulous piece of jewelry. "Whether it's a beautiful faux-pearl necklace or a pair of real pearl earrings, get the best you can afford," says Summers.
Slimming black pants. "Make sure they fit perfectly," he says. "You can cheat with cheaper tops if the bottoms look great."
A sexy black skirt. "If you're tall, have one that hits the knee," says Summers. "If you're short, get a skirt that hits just above."