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What Not To Wear

My closet and I are at war. I'd confront it every day but every day it would impose something bland, boxy and black. I’d curse, avoid the mirror, rely on my sassy accessories to win the day, and then return to battle once more.

I knew I needed outside help when my husband asked, “Do you ever buy anything that doesn’t have a red clearance tag on it?” It finally dawned on me that he wasn't praising my shopping skills; he was asking to see me in clothing that wasn't the wardrobe equivalent of cold meatloaf — a leftover.

To be clear, I am not wearing neon green sweatshirts with the sleeves cut off. They are all designer labels, I swear, but I choose safe over stunning; meatloaf over filet mignon. And I use clothes to cover up the fact that I like both meatloaf and filet mignon a little too much.

My closet and I are at war. I'd confront it every day but every day it would impose something bland, boxy and black.

The intervention came just a few weeks before a birthday ending in a 9, in the form of fashion coach Susan Kanoff, whom I smugly informed that I was not having a midlife crisis, and did not intend to be cougarized in any way. I just needed an objective third party to help get me on the right track to stylish.

Susan told me her goal was to dress me in clothes that fit my body well and make me feel fabulous. “I want your new look to inspire confidence, raise self-esteem and give you an acceptance of your body. Lose the baggy clothes,” she said, nailing my zaftig zeitgeist.

So, into my monochromatic closet we delved. We quickly got into a pattern where I would try something on and she would shake her head and then help me jam it into an ever-growing black trash bag for donation. When we got to the baby blue suede blazer with big, white stitching that I picked up at the Christmas Tree Shops for $10 on clearance (pictured at right ... don’t judge!), I helped things along: “Well, if you hated those, you’re going to despise this!" She made a little gagging noise and shoved it in the bag.

(Courtesy)
(Courtesy)

While I did score points for having some great dress, shoe and purse options, we clearly established that I mostly made questionable clothing choices based on price and an item’s ability to cover up. “I want you in lower necklines, tighter jackets, and get yourself a good pair of snakeskin pumps," she advised. "If you don’t show it off now, you’ll regret it when you’re 80." Ouch. I imagined myself in a rocking chair somewhere declaring to no one in particular, “Honey, be proud of those curves. If I could turn back time, I’d be wearing Spandex to church!’’

But all this wardrobe cleansing was complicated by another issue. I had clothing I could not part with. Susan called these “Sentimental Hold-Ons." The smaller-sized Lucky jeans I bought in Montreal in 2008 were hanging next to the larger-sized Old Navy jeans I just bought at the local mall.

Why? To remind me of the great shape I was in that year, that’s why. I look at them every day and remember pulling them on in the dressing room and thinking, “whoa baby." The memory alone makes me feel great, whether I get back into them or not.

Most women hang onto clothes they used to look good in as incentive to look that good once again, but really, it’s just a form of torture, Susan said. She encouraged me to pack away or purge these items and rely on my memories and photos instead of clogging my closet. And she never even saw the tennis sneakers my husband bought me with a bagful of loose change on one of our first dates (he owned vending machines). Or the Franco Sarto kitten heels I wore to my college graduation. Or the beige trench coat and black Coach bag I bought when I landed my first job as a newspaper reporter.

Most women hang onto clothes they used to look good in as incentive to look good once again, but really, it’s just a form of torture, Susan said.

I did agree that a sleeveless J. Crew shell I bought to wear in Paris four years ago belonged in the Bulging Black Bag of Boring. It made the trip, but I never wore it. Still, each time I looked at its shimmery ruffles (What? the flapper look was in!), it reminded me of how excited I was for that journey. Bravely, I bid it adieu.

Overall, it was an eye-opening exercise that made me rethink my approach to shopping, create a personal style and finally celebrate the body I have and not the one I’m struggling to form. So, I bought those V-neck cashmere sweaters, skinny jeans, fitted jackets and, of course, snakeskin pumps that Susan recommended. Kinda cougary, but I was open.

Try as I might, though, I haven’t found any of the items on my list at the Christmas Tree Shops. But I’m determined to keep looking.

This program aired on December 18, 2013. The audio for this program is not available.

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