Age-Wise Style
Credit: Jeff J Mitchell/Getty Images

InStyle’s special projects editor Cindy Weber Cleary has been a fashion editor for the past 20-plus years. Needless to say, she’s picked up some tricks along the way. Catch her column here each week for how-to tips and style secrets on her favorite, timeless styles.

"OMG. Everything online is 60 to 70 percent off!" This hits me like a double macchiato. Heart pounding, I can hardly keep my fingers on the keys.

I have always been a competitive shopper. Even as a child, I wanted to be “the first out of the gate.” In sixth grade, I distinguished myself as the early fashion-adapter when I showed up in Mrs. Brett’s class wearing red wooden-soled clogs from Olof Daughters of Sweden. (Obviously this meant a lot to me since I still remember the brand!)

When I became a fashion editor in my 20s, I was surrounded by gorgeous designer clothing that I couldn’t afford. So I discovered the thrill of bargain shopping. I especially loved going to the “back room” at Loehmann’s, where top designer clothes were sold at deep discounts with the labels cut out. Because of my training, I could identify a Geoffrey Beene, here, a Giorgio di Sant' Angelo, there—and nothing felt better than scoring something fabulous. But often the game went to my head, and I’d find myself the proud owner of a glamorous pair of palazzo pants or an avant-garde Japanese tunic with extra sleeves—and nowhere to wear it.

As they say, with age comes wisdom. So now when I shop the sales, it’s with a discerning eye and a poker player’s intuition about when to fold. This is the time you can really find some unique, heirloom-quality pieces at a fraction of the original cost if you have a smart shopping strategy (in addition to the fire in your belly). Follow these three tips:

1. Filters first: Take advantage of whatever filters shopping sites offer, especially size, designer/brand, and price. Why waste time scrolling through an overwhelming, unedited array of merchandise only to find that there is just one piece left in a size 2?

2. Look for timeless shapes with special details or luxe materials: A quick search of Net-a-Porter today turned up a gorgeous grey shearling coat from Karl Donoghue marked down from $3,260 to $1,304. This is something I could wear forever and would thank the shopping gods for whenever the temperature dips below freezing. But that Pop Art–patterned Valentino dress from fall is too recognizable to amortize the cost.

3. Be open to serendipity, but be realistic about your lifestyle: A Mary Katrantzou gown marked down from $16,000 to $3,000 is an incredible bargain, but do you have somewhere to wear it (or the money in the bank)? A pair of Narciso Rodriguez ankle-boots reduced from $950 to $285 seems like a better bet.

Here is what I scored:

Age-Wise Style
Credit: Courtesy

Jason Wu satin crepe midi skirt, $449 (originally $1,285),; Altuzarra bi-cool wool blend coat, $1,371 (originally $2,743),; J.Crew belted shirt dress, $100 (originally $148),; Narciso Rodriguez ankle boots, $285 (originally $950),; Pierre Hardy color block clutch, $499 (originally $1,275),