Several years ago, I went out to lunch with Laura, an old college roommate. I got dressed with the usual minimal care to my appearance but thought I looked OK. My hair was combed (out of its usual messy ponytail); I had makeup on (unusual—I work from home); and I was wearing a blue-and-white striped nautical top, along with a cute pair of overalls.
Laura looked me over and sighed. "AGAIN with the overalls?"
I was stung. "I think I look nice," I said. After all, these were my dressy overalls—the ones that featured a slimmer cut and hugged my hips in the way my everyday ones do not.
She shook her head disapprovingly.
Despite the fact that I've reached middle age, overalls have been my go-to for years. What's not to love? They're comfy. They're roomy. They're versatile. And the pockets! My iPhone, my reading glasses, and an extra pen or pencil fit easily into the front bib. My cash, credit card and ID (I rarely carry a purse) go into another. A T-shirt, overalls and Birks, and I'm ready to face the day.
Yes, friends will occasionally call me out on this sartorial choice, but it didn't occur to me that overall-wearing was at all questionable until I started dating a man (let's call him Peter) a year after my divorce. When I texted him something about my overalls, his response was definitive, "Yuck."
Was he kidding? "I look super cute in these overalls," I texted back, but it did give me pause. Then I shrugged. Why should he care what I wear, anyway?
It wasn't that I wore them all the time. I had other items of clothing: jeans, a few skirts, even actual dresses. I just rarely dressed up. The truth was that when I did bother, I felt (sorry, inner feminist) pretty. Then the next day would arrive and I'd slip back into my comfort zone.
The third time I went out with Peter, he told me he wanted to take me "someplace nice." So I hit T.J. Maxx on a search and destroy mission and walked out with a gorgeous Diane Von Furstenberg sheath that fit like it was made for me; sleek peep-toe platform pumps; a new bra that would fit under the neckline of the dress; and even new thong underwear—you know, to go with the bra. (Like I said, this was a third date.)
Then I got my nails done. And a pedicure. And got my hair cut, colored and blown out. When I finished my makeup and pulled on the dress and looked in the mirror, I was gob-smacked. I called my best friend. "I look smoking hot!"
"I require proof."
I texted her a full-length selfie and my phone immediately rang. "Someone is getting laid tonight," she sang.
I couldn't stop admiring myself. "I look better than I have in 15 years!" I said. I certainly felt better. Later that night, at dinner, I gestured at my dress. "You see this dress? The shoes? The hair? The nails? All of this?"
"Yes, I see," Peter laughed. "Special night, huh?"
I wanted him to understand that this girly-girl teetering in peep-toes wasn't how I usually rolled. "This is all for you," I said.
"I appreciate that. You look great," he said. "But you should do it for yourself."
"I don't care about doing it for myself," I countered. "My self-esteem isn't based on my appearance, or what I wear." Hey, I'm evolved. I know the outside stuff doesn't matter—it's what's inside that counts.
Besides, my former husband had never seemed to care—or even notice—what I wore. Over the course of our marriage, he gradually withdrew from me. He was sometimes angry and often flat-out unhappy, and our sex life—what was left of it after six years of infertility and two kids, four and a half years apart—suffered.
Not surprisingly, the less I felt wanted, the better those overalls felt. I didn't want to think about my body, or what I looked like to the outside world, or about how I wasn't getting touched. In them, I was shapeless. Hidden. Safe. They were my go-to for years—and throughout our separation and divorce.
But when I started dating again, I realized I needed to step up my game. I did the online dating thing, communicated with dozens of guys and went out on 9 or 10 "encounters." (I refused to call them "dates.") I ditched the overalls for a cute outfit, did my hair, put on makeup and let nature take its course. Many times I was home before 9 o'clock.
I met some nice guys but no one I could even imagine kissing—until I noticed a man at my local Y. Peter was tall, friendly and attractive. I checked him out surreptitiously in the mirror a few times. Hmmm. Actually very attractive. I started chatting with him to figure out whether he was single (yes); at least minimally intelligent (yes); and not a Nazi or a nut (signs pointed to no). I then suggested that we go out sometime.
Weeks later (single parents' lives are complicated), we went on a real date. We talked, laughed, flirted. Our knees brushed against each other at the bar. And I felt something I hadn't in years: electricity. I wanted to touch him. I wanted to kiss him. I just wanted him. When he kissed me in the parking lot, I realized how long it had been since I had felt wanted.
Being kissed—and kissed well—by someone I desired started a cascade of feelings I hadn't expected. Suddenly, I was eyeing my pathetic wardrobe with concern. I went shopping. I bought dresses. I bought heels. I ditched my ancient, stretched-out bras for lacy, sexy ones. And people noticed. One mom at a school, who had never seen me out of overalls, looked me up and down, and said, "Kelly! You have a body!"
Yeah, I do. I had just forgotten about it.
"You know how in 'Jerry McGuire,' he says, 'You make me want to be a better man'?" I said to Peter one night. "Well, you make me want to be a better dresser."
My inner feminist groaned. Did you really just say that? A man made you feel this way?
I attempted to appease her by slipping back into my overalls—my baggiest, roomiest pair—the next day. I was on deadline and they welcomed me back. The next morning, though, I bypassed them for one of my favorite print dresses. I put on makeup, did my hair and slipped on heels. I looked … beautiful. Confident. Polished, even. Like a better version of myself.
I am a better version of myself. After years of hiding my body under the guise of comfort, I've learned that it's OK to take some pride in my appearance. To dress with intention rather than habit. To like what I see in the mirror instead of acting like it doesn't matter.
I know it's what's on the inside that counts—but there's nothing wrong with sprucing up the packaging.