About ten years ago, I lucked into a dream job managing a punk rock band that, for a while, rode a crest of some fame in Cleveland, Ohio of all places. I was in my early 20s, making more money than I knew what to do with at the time, and booked an out of town gig for the band in New Orleans for Halloween. It was a fancy affair, so when we arrived in Louisiana, I realized I didn’t have anything nice enough to wear for what shaped up to be a phenomenal night, so I splurged at Saks Fifth Avenue for a whole new outfit.
I spared no expense that day, and bought a Donna Karan velvetine shirt that felt so soft, so warm, so luxurious, I must have run the material through my fingers a thousand times, fascinated, in complete awe that something so wonderful could actually be mine. It was definitely a step up from the closet full of Gap, Banana Republic, and J. Crew back home.
I paired the shirt with a pair of size 28 Dolce & Gabanna jeans that I could never dream of squeezing into again today, if my life depended on it, but back then I rocked like nobody’s business.
The last splurge was a pair of Gucci boots that cost more than I’ve spent on shoes, total, in the decade since (averaging about one new pair a year, when the old one wears out, I’m not a big shopper, especially when it comes to shoes).
In that outfit, I really did feel triumphant and magical. It felt like all eyes were on me, in a good way, in a great way, actually. I went to our concert that night, did all the press I needed to do, and rocked the after party in my fantastic new threads. Looking back, it was really one of the most spectacular nights of my life — an extravagance I’ll never repeat, but one I can’t say I’ve ever regretted, because it was my very own personal “Pretty Woman, they finally let Julia Roberts shop” sort of scene.
And the fat, pimply-faced, awkwkard kid that’s always still inside me, no matter how old I get or what I do with my life, got to put aside all of that awkwardness for a night, and rock out like the rock stars he managed. He got to feel as cool as the guys in the band. And he truly, deeply, loved those expensive new clothes.
Loved them a little too, much, to be honest.
Because long after I stopped managing the band, I kept that outfit in my closet, in plastic bags, for special nights out. Whenever I needed that extra boost of confidence, whenever I needed to feel sexy, I put that Donna Karan shirt on, and squeezed (with ever greater difficulty), into those incredible jeans, slipping into those boots (which, for the fortune they cost, sure fell apart quickly).
After a while, people started to politely notice I “was always wearing the same shirt”, after one too many times of telling me how much they liked it, and the seemingly unalienable luster of that velvetine began to fade away. Probably three years had gone by since that Julia Roberts moment in New Orleans, and I had no idea how ridiculous I started to look, always sporting my now signature, dated, absurd “style”.
And then, one night in grad school, I rocked my “favorite outfit” for the very last time, the night before a class I couldn’t miss, at a party I really shouldn’t have gone to (for my own good). As parties are apt to do, especially the good ones, what was supposed to be a 2am night lasted well past dawn and far into breakfast. Two trains and a cab later, I slinked onto campus bleary-eyed, in the clothes I’d worn the night before, reeking of cigarettes from the days when bars still filled with smoke all night long. I was an absolute mess, dead tired, walking around a sunny college campus as absolutely out of place as a person could be, where everyone else looked like they stepped out of an Abercrombie catalog, while I seemed to have tumbled out of a relatively sedate Cher video.
People stared, and not in a good way.
Some people even giggled, because I was so totally out of place, and what I was wearing was so ridiculously inappropriate.
The class I had that morning was once a week, and the sort that I wasn’t allowed to miss without failing. That day, the professor, of course, had be give a presentation to the entire 100 person class…when I became painfully aware of how ridiculous everyone thought I looked. It was a nightmare.
An absolute nightmare.
And after the class, I headed back to my apartment, where I stood in front of the full length mirror, in the scalding light of day, and realized how truly stupid I looked in velvetine at 11am in Cleveland.
No matter how great my “favorite outfit” looked once upon a time, or out at a night club, it was ridiculous and inappropriate for walking around in the daytime, or for going to class or work in. As much as I loved wearing those wonderful, expensive, enchanting clothes — and as much fun as I always had in them — I realized it was time to put them away, at least for a little while, and start wearing things that were more appropriate.
So, when I see Michelle Obama wearing sleeveless dresses to Obama’s speech before Congress or in her official White House portraits, or watch her don inappropriate cocktail attire to the Inauguration, with a hideously unflattering gown for the balls, I actually feel empathy for her, because I’ve been where she is now.
And I’ve seen pictures of Michelle from high school, and know she was never number one on anyone’s dance list, and realize a lot of the skowls she makes or attitude she projects stems from growing up awkward and lanky, with unflattering, unglamorous clothes.
So, now that she has the opportunity to revel in attention, wear expensive things, and grace the covers of magazines, Michelle heads for the sleeveless dresses that are her personal velvetine Donna Karan shirt and tight Dolce and Gabanna jeans.
She doesn’t seem to have anyone to tell her how ridiculous she looks in sleeveless dresses in winter, anymore than I had someone to call me out for wearing that Donna Karan everywhere. Sure, people laughed at me and made comments, some of which I heard, while others were shared behind my back. But, being human, I generally only listened to people who complimented me, just as it seems Michelle’s only paying attention to those who call her a fashion icon, ignoring those who called her Inaugural gown a Flintstones-inspired Yabba Dabba Don’t.
Michelle Obama’s allergic to sleeves because inside she’s an awkward, challenged girl, still, wanting to dazzle the way she always imagined she could, without regard for the appropriateness of that dazzling in February, at events that are not cocktail parties or balls.
She wears sleeveless cocktail dresses the way I wore nightclub clothes to class on campus, in broad daylight.
And she looks as ridiculous as I did back then.
Will she realize this one day and start dressing appropriately?
Yes, of course she will.
Just like I did.
Who knows when it will happen, but maybe she’ll begin to compare the photo album her staff’s building of her time in the White House with the First Ladies who’ve come before her, and she’ll start to see how inappropriate evening wear is during broad daylight.
The antidote to her sleeve allergy is historic perspective, and the realization that the four years she’ll spend in America’s house are something that will live on long after she’s gone, and could either be the butt of retrospective fashion jokes, or could be timeless and memorable in all the right ways.
It’s up to her how she’ll be ultimately remembered and represented in all the history books. But, she hasn’t been in this role long enough to realize that yet.
The sleeveless dresses will be put away in time, I’m sure.
But, they’ll never be thrown out, of course. Because I still have that Donna Karan shirt in my closet, wrapped in plastic, as it’s the only designer shirt I’ve ever owned, and still enjoy pulling it out every once in a awhile to see if it still fits, and to feel that marvelous velveteen and remember how clueless and excited I was a lifetime ago when I first bought it.
So I think I understand why Michelle’s doing what she’s doing, and also know she’ll evolve out of her sleeveless phase in time.
It won’t be soon enough, frankly, but like with me and my own “favorite outfit”, it will be better than never.
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