Finding Festive Fashion at Sears

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It’s not that I’m a snob. I just really, really like clothes. I guess 12 years spent sporting plaid, pleated, polyester skirts will do that to a girl. “Free Dress” days, as they were called at my private, Catholic schools — the days when I could skip the uniform and actually dress myself — were special; they meant freedom, but more than that, they meant fun. To this day, glossy fashion magazines hold the allure of porn; I am powerless to resist them.

And while, gathered together and stacked, the Vogues, Elles, and Ws I’ve pawed through and drooled over in my lifetime could rival Mount Kilimanjaro in size, the items that stuff my closet need not be (oh, let’s face it, are not) big-name splurges. Label-lust aside, I’m hardly above a bargain: I love a deal as much as the next girl, but, historically, my bargains have taken the form of designer knock-offs, or one-off vintage scores. In other words, I don’t care how cheap it is: If it ain’t cute, why bother? Which is why this challenge, dreamed up by a team of evil coworkers hellbent on pushing me well beyond the confines of my comfort zone, proved so daunting: to put together a cool, holiday party-ready outfit at (wait for it) Sears.

Was this even possible?

I had no idea. Until this little experiment, my time on the softer side had been spent with electronics, appliances, the occasional power tool. I mean, clearly, if you’re in the market for a new refrigerator or a clock radio, Sears is the place to go. But clothes?

Piling into the car with a semi-willing male counterpart in the form of news reporter Chris Meagher, two officemates, and one boss, I guess you could say I was cautiously optimistic, in a this-will-never-work kind of way. Upon entering, I was decidedly less so.

Holiday Fashion

The men’s department greeted us, so Meagher was up first. He wasn’t sure what size pants he needed, and indicated that we should check the tag of the trousers he was wearing — at which point we learned … well, we learned more than we wanted to know. Man goes commando.

After determining what size we were looking for and doing some serious digging, we came up with two pairs of dress pants — one black, one pinstripe — and two dress shirts — one striped, one adorned with a gridlike pattern. Looking up, we stopped our madcap poly-pawing. “Wow, that’s actually kinda cool,” we agreed, before getting back to work.

The ladies’ department was a different story. We rifled through … Every … Single … Rack. And with each rack, the panic intensified. My size didn’t help matters: I’m wee, and, not only were the smaller sizes in short supply, it seemed to me that the clothes ran really big. Eventually, we came up with a couple of skirts — the most promising was a black, A-line, with a lacelike overlay. Finding even the most basic of tops proved difficult; everything seemed to have been tagged by the bedazzler. This was not looking good. In fact, it was looking like a sartorial version of Supermarket Sweep. On acid.

Holiday Style

In need of comfort, we detoured into shoes, and I actually fell in love with a cute little pair of heeled, white Mary Janes ($44!). I asked for a size 6 ½ or 7; the saleswoman came back, offering me a 10. Boo.

After scouring every inch of floor space, we made our way to the women’s fitting rooms, smuggling in the underpants-free Meagher beneath a pile of frocks. Dockers-defiling aside, his portion of the endeavor went swimmingly. He looked great in every possible combo of the items he’d brought inside, although a pair of older ladies who’d heard his voice from behind the locked door shot us nasty looks. Frequent firing of my camera’s flash did little to comfort them. After approximately two minutes, he was done. We placated him with a donut.

Meanwhile, I was not having much luck. Everything looked shapeless, frumpy, blah. It was clear that this mission called for serious creativity. We sent editor Aly Comingore back to the battlefield on an emergency mission (“Belts!” I yelled), and she returned with more options. I grabbed a black, ribbed top, and tucked it into that lacy A-line skirt, hiked as high as it would go. I tried a skinny black belt with it, but it just didn’t work. And then I swiped a wide, silver-metallic belt, snagged from a discount bin; it was my last resort. Fastening it, I looked in the mirror, and blinked in disbelief. This little ensemble was, in fact, rather adorable. Definitely party-worthy.

One hour and 14 minutes later, our mission was accomplished. Which left us plenty of time to shop for toasters.

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