How I Made a Makeup-Free Day Feel Sexy

I debated taking up this Challenge. Sure, I often go makeup free… but only when home and relatively alone. Today, I had to go out into the world.

I’m not the tousled-just-outta-bed-sexy-look kinda gal on the best of days. I have the uneven skin of any normal thirty-something woman who works and has lived a life. My skin is still recovering from a char, received from a run-in with a violently over hot tea served to me over a week ago. Today I’m extra-tired, too. Way too tired for a Monday. The kind that makes my eyes pinch and my hair hurt.

Up at six-thirty in Connecticut, I’d tackled a long list before driving back to New York and tackling the second set, all bare-faced. Before running out to the radio station mid-afternoon, I took my makeup bag to the bathroom figuring that, at the very least, a layer of thin base and a swipe of mascara might brighten things up and make me feel dewy and fresh and radio-energy-ready. Then I stopped. I had to shake up a habit.

Would I feel that repellent if I went out bare faced?

I figured I’d try.

From Washington Heights to Bushwick, with countless people to run into and see in between, I’d go out with the puffy eyes and blotchy skin and charred lips and see if anything changed. I rubbed in another layer of almond oil to help lube up and swiped on some more clear lip balm, and that’s it.

Looking in the mirror and contemplating my ensemble, I came up with an idea: I’d balance the mess with a touch of glam; glam in the form of artfully ripped jeans, a long black sweater, a giant fuzzy vest from the 70s I got at a vintage store a few years ago, and winged sunglasses — the kind of casually fashionable look I can only pull off once every second harvest moon.

Today, it worked.

Out the door sans makeup, I immediately run into a neighbor — a celebrity hairdresser — who tells me I look amazing. I know this is the work of recent weight loss and the fuzzy vest and the sunglasses and the intentionally frizzy hair. But given the bare face, I’ll take it.

I’ve brought along a “vintage” book, too — Lisa Bright and Dark — and a dude reading it with me over my shoulder on the L train doesn’t make me feel repellent, either.

In Brooklyn, I don’t feel out of place at all. Bushwick is Bushwick, and I often feel overdressed there when wearing clothes not bought secondhand, so the makeup-free look seamlessly blends in with the crowd. The fuzzy vest has made the ensemble — it’s a conversation starter that helps mask the even-puffier eyes and over-exhausted every-other-part-of-me.

On the trip home, I curl into it. As I meander through rush-hour throngs of bodies on the subway wind home, I notice I’m swirling my hips a little in my walk from place to place, too. There’s something about this that feels a bit rebellious. This choosing to feel strong and sexy, wearing ripped jeans and a second-hand oversized sweater, and a vest I once thought far too large for my short frame that I now want to wear everywhere. This baring of my honest skin to the world.

Later, I ponder how those who don’t ever wear makeup don’t need to worry about washing their faces every night. About how that’s probably much better for their skin. And how, packing on year after year of twice-daily washing, plus those decades of having layered stage makeup on my skin, too, it’s probably an excellent idea to forego makeup when I can for the sake of all this pull and puff.

If I can go makeup free and still feel like a badass chick, getting things done despite not looking or feeling my best?

I’ll shift that habit up more often now and then.

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