What To Wear: Summertime First Date

Q. Hi Jordan,

I read your blog every day and love it. I particularly admire your style choices and wanted to ask: any thoughts on what to wear on a first date during the summer? I’m facing a few dilemmas which include the fact that I’m likely going there straight from work. Thanks!

Best,
Katie

A. First dates for me are like first days of school. And what I wore to every single first day of school ever (seriously; I’m weird that way) has been a variation on white shirt/blue jeans/brown leather accessories/one pop of color.

Sorrrrrt of like this, only much less cutoff-y (when it came to clothing, my school was pretty cool…but no one’s school is that cool).

Why?

Two reasons: 1) That’s my comfort-zone outfit, and when put into uncomfortable situations I like to be certain that I’m going to feel good about what I’m wearing, and 2) I think it’s nice, when getting to know new people, to showcase your personal style to some extent (back to the whole idea of the “comfort-zone outfit”)…but not to go so far in any one direction that you have to fight to make your personality heard over the noise of your clothing.

You know when I abandoned this rule? On my second date with Kendrick (and my first that took place at a normal hour of the day rather than at 3AM). I wore – and this is true:

1. Black knee-length shorts over black opaque tights

2. Enormous black platforms

3. A black tank layered under a navy boyfriend-style knit cardigan

4. Really not good clip-in hair extensions

and…

wait for it…

5. A black knit beret.

In Los Angeles.

Which, in case you’ve never been, does not have the same climate as mid-winter Russia.

In case you’re having trouble picturing the sheer extent to which this did not look good or make sense, here’s a helpful artistic rendering:

I have no idea what I was thinking, either.

(Apparently Kendrick had a similar reaction: his very words – said to me many months later – were: “You looked like an Olsen twin and I thought you were crazy”.)

Anyway, that’s a long and roundabout way of saying that (taking into account that I don’t know how formal your office is or where you’re going on your date), here’s what I’d wear:

1. A sweet floral dress toughened up with some leather bracelets and a pair of snakeskin (I love mixing snakeskin and florals) heels. At the office during the day, you can cover up with a cardigan and swap in a pair of gold flats.