1. Shop at thrift stores and consignment shops. Make sure you're well rested and drink plenty of fluids if you want to get the best bargains. In fact, make it a trip with your girlfriends and see who can find the best deals. Try looking for items you can easily make fresh and new. Buy a t-shirt dress and a belt that contrasts the dress; for example, a fuchsia dress and a brown belt to wear around your waist. Then, get creative by changing the buttons, cutting it shorter, or adding patches.
A guide to thrift shopping in DC: http://dcgoodwillfashions.blogspot.com/
The "must go-to" consignment shop in Brooklyn: http://www.beaconscloset.com/ ( amd make sure you go to the one in Brooklyn)
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2. Buy staple items out of season. You always need a pair of black winter boots, a peacoat, a "go-to" swim suit, or a timeless Little Black Dress. Buy the winter items in the beginning of Spring and Summer items in the beginning of Fall. You get everything for 50 to 75%.
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Target; $11.24
http://www.target.com/Isaac-Mizrahi-Target-Polka-Dot-Eyelet/dp/B0015CDNGK/qid=1238037862/ref=br_1_16/190-5562314-6975369?ie=UTF8&node=10828011&frombrowse=1&rh=&page=1
3. If you can't live without your designer duds and don't want to buy them second, then shop at places like Filene's, Loehman's, Off 5th, TJ Maxx, Nordstrom Rack, or Ross. Make sure to take your time and be patient when you're looking; patient people find the best deals.
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