I know what you’re thinking — in some ways, I’m thinking it, too: Who am I to give you dating advice, right? I’ve built a business on the art of repelling men using expensive footwear and sometimes pants that flare just a little too wide. And this, this in spite of the fact that I was married at a tender 23. So, really, am I the authority on what you should wear if you have a date slated for this week?
But I ask you to consider this: Amelia, who typically likes to scribe these stories, is still single.
I, on the other hand, am not.
So, let’s proceed! Shall we? The way I see it, if you are, in fact, going on a date, the three most likely scenarios under which you are to find yourself are as follows:
+Some version of an event where you will be among his or your own friends to make it seem more casual
So what’s a girl to wear?
For a day date:
Converse will trick your opponent into thinking that you’re cool. Interesting pants that are casual enough not to raise eyebrows but still dynamic enough to raise like a single follicle in one eyebrow will suggest there is more to you than meets the eye. More than your fupa, even. Black pants look cool when paired with a denim jacket. Denim jackets look great with black coats over them. I’d recommend something red under the panoply of non-color because you, my friend, are the life of the easel.
For evening drinks:
I ask you to consider what you would wear if you were having drinks with a close friend who you haven’t seen in a long time, who you’d also like to make a good impression on because it’s been so long and last you heard, she’s got a great job and maybe she doesn’t realize that you have a great job, too, that you’ve totally moved past Limited Too and practically have Phoebe Philo on speed dial, though you still appreciate a pair of conversation starter shoes, so! Lo and behold: your most reliable pair of jeans (are they high waist? Are they flared? Maybe they should be?), with a striped, long sleeve t-shirt and a button down of your choosing layered over the t-shirt. If you want to add another layer to the onion, I ask you to consider socks that strike in another direction.
And as for the shoes? Show stoppers, please!
For a vaguely dressy party wherein multiple members are involved:
You don’t necessarily have to look like you’re about to cry, but I’d ask that you pair two of your favorite garments of the moment from the pile of Shit that is Outlandish in your closet, break them up with a simple knit (a tissue turtleneck rarely fails) and then try flat shoes because wearing flats on a date makes running away much easier.
Of course, if you don’t have a date, just text me. I’ll be eating goat milk ice cream in bed and watching terrible, terrible TV.
Photographed by Krista Anna Lewis.