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Cindy Weber-Cleary
Jul 09, 2015 @ 5:00 pm

Shopping, like chess, is a game of strategy. If you master a few key moves, you can save yourself a lot of money and build an interesting wardrobe while you are at it.

When I was starting out as a fashion editor, I had a very limited clothing budget. I supported myself on a salary that served as pocket change for the many “trust-fund babies” who chose to work in the industry. I remember one, who used to toss her paychecks in her desk drawer and forget to cash them! I had to be shrewd about my purchases in order to dress well. So, I prepared for end-of-season sales as if for a tournament.

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Today, the rewards are exponentially greater, since online sales offer a much broader range of merchandise and you have the added advantage of shopping filters, which can show you everything in your size and price range with the click of a finger. That said, I still have some secrets to share.

This is the perfect time to shop the more expensive sites in search of high-quality items at a deep discount. Most sales offer discounts from 40-70 percent at this time of year.

I approach the sales online with three separate game-plans:

1. I look for very special designer pieces that I usually can’t afford, including classic shapes in gorgeous fabrics or with unusual details that I can wear for many years to come. I avoid anything that is too recognizable from a particular season so that I won’t look dated.

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Shop the pieces: Osman dress, $690 (originally $1,551); matchesfashion.com. Altuzarra shoes, $518 (originally $1,295); saksfifthavenue.com. Fausto Puglisi coat, $596 (originally $1,489); farfetch.com.

2. I look for perfect staples, such as a tailored blazer, a knee-length pencil skirt or wide-leg trouser in seasonless fabrics, such as silk, cotton, lightweight wool, and cashmere. You may be surprised at how much of the clothing from spring/summer can be worn into fall and beyond. The traditional seasons of dressing have blurred. Sure, you may be able to find similar items at a lower price, but there is a real pleasure to knowing that your basics are well-made and will probably fit better and last longer than their fast-fashion counterparts.

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Shop the pieces: The Row blazer, $1,231 (originally $2,462); mytheresa.com. Theory skirt, $398 (originally $995); hampdenclothing.com. Lanvin purse, $1,750 (originally $2,195); modaqueen.com.

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3. I look for moderately-priced sale items that are of the moment. This can give your wardrobe a shot of newness. The strategy requires a little bit of homework on your part. Take some time to go online and research the upcoming fall trends. Choose the ones that appeal to you, then look for similar items currently on sale. I chose three: sophisticated florals, choker necklaces, and culottes.

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Shop the pieces: Tibi culottes, $285 (originally $475); matchesfashion.com. Nicholas skirt, $373 (originally $745); shopbop.com. Alexis Bittar choker, $176 (originally $295); bergdorfgoodman.com.

I hope this plan of attack was helpful! If you have your own sales-shopping gambits, please share them with us @InStyleMagazine.

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