Editor’s note: Meet Cary Randolph Fuller, our newest Date Report columnist. Every week she’ll share tips for how to date in style. Need fashion advice?

For this, my inaugural Dress To Impress post, I’m going to share a story about a very HowHookup-esque date and the unsexy outfit I wore that, as luck would have, didn’t turn out to be unsexy at all. In fact I use this anecdote frequently to illustrate my belief that we are never going to know exactly what the opposite sex wants to look at.

In May 2020 a man who follows my Tumblr emailed me, offering skateboarding lessons. (I had recently posted a desire to learn.) We set a date for the following Thursday evening and agreed to meet by Chelsea Piers.

A few sartorial red flags: this was a casual date that would likely involve skinned knees and elbows, we had met on the Internet (the horror!), and I was coming straight from work, pencil skirt crammed in a duffel bag. I needed to look cute but somehow professional and frame the entire outfit around flat-soled sneakers. Running late and nervous as hell, I settled on the following mishmash: olive drab cargo shorts, a black cardigan, Converse, and no makeup save for a haphazard streak of red lipstick.

Now a “normal” first date might require cleavage and a blow-out or perhaps a tie (for him), but there is no such thing as normal anymore, and sometimes – especially when skate parks and beer are involved – it just makes sense to dress like, well, in my case a tween on summer vacation. No, I didn’t look like a fashion plate, but neither did he, and the goal was to do something kind of crazy, at which we succeeded.

We dated for exactly one year.

A date’s success isn’t dependent on fashion, but when you adequately convey a sense of style and comfort, you put the other person at ease. This is why I never advocate five-inch heels or tuxedos until you’ve had the relationship talk. Why suffer…yet?

Cary Randolph Fuller writes for fashion sites including Selectism, Guest of a Guest, and Nonsociety. Between assignments she searches far and wide for the Endless Summer – tweeting, skateboarding, and baking cobbler. She lives in Saint Louis, Missouri.

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