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Adult Playdate: What to Wear?

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Damn, my hair looked too good. I tried to unperfect the perfect straightening job by slapping on a little extra smoothing balm to make it look greasy, and then pulling on and off a tight woolly hat to achieve a convincing head of I-didn’t-try-too-hard-hair. This was my first playdate and I didn’t want to alienate my potential new friend by looking too pulled together.


Jessica and I had exchanged phone numbers and noncommittal we-should-get-togethers months previously, but it was an accidental encounter earlier in the week that had lead to actual plans for breakfast. Our kids knew each other so we’d chatted a few times at sports or school events, but never without the distraction or crutch of the kids. She needed help translating the lyrics of an Irish song, so we made plans to meet after dropping the kids at school.


A kid-free playdate.


I could wear white if I wanted to … but white in winter might be too eager. Black? No, it might be too slimming. Pink? Too girly. Floral? Trying too hard. Grey? Yes, grey. You really can’t go wrong with grey—it’s stylish but it’s also just grey, and grey is just fine. I settled on a light grey cashmere hoodie—the hoodie kept it casual, and the cashmere would keep me warm. Perfect.


Now, what to wear with the hoodie? Definitely not a dress. The one thing I had learned in my years of dropping kids to school is that out of respect for (read “fear of”)  the other moms, you just don’t wear a dress until at least 11am, with the exception of jersey dresses (a jean alternative) in summer, and only then if worn with flip flops and a chipped pedicure. It’s part of the unspoken mom-code. Lip balm not lipstick, antiperspirant stick not perfume, and sneakers or flats, not heels. Hats are appreciated because they imply unbrushed hair, and an effort to hide it (rather than comb it). It’s okay to look like you’re off to the gym, just not okay to actually mention it (unless you follow up with self-deprecating references to your fat ass and lumpy thighs).


I detest the drop-off drama and so I have avoided befriending “the moms,” though I’m sometimes a little jealous when I see them hugging and chattering at the school wall. It’s impossibly difficult to find time to “make friends” as a grown woman, so when Jessica—a sane, normal, and interesting person I’d actually enjoyed chatting with—suggested plans, I was eager to appear similarly sane, normal, and interesting (surely I could pull together a look to fit this part?). I imagined she wouldn’t notice, never mind judge, my outfit, but I was making an effort (not to make too much of an effort) just in case …


After eliminating the dresses and all the pants in my closet (for varying mom-code violations), I wavered between my one pair of fitted but almost threadbare jeans that I wear all the time, and my one pair of wide-leg jeans that I should wear all the time, but I somehow always end up swapping for the threadbare pair right before I leave the house. I relaxed as I felt my playdate outfit come together: a grey cashmere hoodie, with a white (but not brand-new white) tank top, and a pair of wide leg jeans.


Shoes? We’d be walking back from the diner together so I needed shoes I could talk and walk in—quiet flat shoes.


The night before I had prayed for rain so I could wear my wellies. Wellies are friendly—like dimples on my feet, and best of all I can wear whatever socks I like inside them. But it was a dry, cold morning—which served me right for not giving anything up for Lent—so my wellies were out, damn.


I reluctantly bypassed my flip-flop collection and reached for the cute but slightly battered pair of black and grey tweedy flats. Shit, which socks? I hate socks—that’s why I’m strictly a heels, wellies, or flip-flop person. These flats look so much better without socks but I’d have to wear some kind of stockings with them—not because I was worried about getting a cold in my kidneys as my grandmother always warned, but because I might look odd venturing out without socks in 24° weather. I tried a few different pairs and settled on the knee length thin-knit pair, but wasn’t happy about it.


With only a few minutes to spare, I applied some light foundation to even out my skin, dabbed the unglossiest lip-gloss I owned, and debated plucking my eyebrows. I needed to have my eyebrows done, and I’d been letting them grow in to get my money’s worth. Face pressed to the mirror, I wondered if my unibrow made me appear artsy or feminist … or uni-bomber? I backed away from my reflection figuring that a raw newly-tweezed brow would be worse. I grabbed my tweed cap and angled it slightly down over one side of my face/unibrow, put on my favorite clear acrylic earrings (to distract attention from my unibrow), and raced down stairs to get my scarf, gloves, and coat on—at this rate, I’d need another fifteen minutes to decide on the right mix of patterns and textures.


I hadn’t wanted to be early but with all my fussing, I was now late. I grabbed my grey coat and purple plaid scarf and headed out the door. Realizing I’d forgotten my phone, I raced back upstairs … and changed into my threadbare jeans.


Jessica wore a wool sweater, though I can’t remember what color. I have no idea if she wore jeans or pants, but she didn’t wear a dress. She was hatless and her hair was brushed, maybe even blow-dried (so obviously she didn’t care that other “moms” might frown upon her stealing time from “those poor kids” to shower and dry her hair so early in the morning). Despite my unibrow, we chatted easily for over three hours and had to leave many half-started threads of conversation dangling, to make room for the diner’s lunch rush.


Next time I won’t waste any valuable chat time by overstressing the dressing …

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