My Looks

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!


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).


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


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:Summertime First Date

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.

2. A relaxed denim button-down (look for a tissue-paper light fabric) over capri-length white jeans, gold hoops, and some seriously amazing wedges (this is the one I’d lean towards). In short: totally casual (to decrease the first-date pressure), but with fantastic accessories. During the day, you can swap in loose grey trousers and flats, and add a scarf to the top.

With both looks, I’d suggest an easy summer beauty look (’cause it is humid out there these days): brown liquid liner (Elizabeth Arden’s is ridiculously water-resistant), bright, glossy lipstick (try Lipstick Queen Glossy Pencil), and a loose, tendril-y updo with a bit of anti-frizz product (Dove Style+Care Frizz-Free Shine Cream-Serum is awesome).

Again, though, I don’t know how formal your office is, and maybe you’re straight-up wearing tailored black suits all day, every day. In which case, the next piece of advice I have is this: there is nothing wrong with carrying a full extra outfit to work and changing into it in the bathroom before leaving. I know, every single fashion advice column says to just swap out your shoes and bag, put a bright and cheery blouse under that blazer, and head straight to the bar…but you know what? That’s what oversized totes are for. New outfits on first dates are fun. Go have fun!

(Seriously, have fun!!!)


Product info after the jump.

Rebecca Taylor sleeveless dress
$291 –

CP SHADES linen shirt
$175 –

$38 –

True Religion white pants
$230 –

Lanvin wedge shoes
$954 –

Aperlai high heel shoes
$1,095 –

Proenza Schouler leather handbag
€1.695 –

Alexis Bittar gold hoop earrings
$145 –

Stella Dot leather bangle
$59 –
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