Last week’s post on dating led to a couple of requests for me to tell you what I wear when I go out, and while I don’t think I’ve even begun to get it down to a science, I’m more than happy to share. I subscribe to the philosophy that you should go for a look that is just slightly sexy on a date: I should probably go with tighter clothes, but I almost always wind up wearing a loose top and tighter pants, because that is what I own (I almost never wear dresses, at least on first dates, for no particular reason). On a recent first date that went very well, I wore a white, collarless cotton Isabel Marant button-down, half-tucked, of course. Nothing makes me feel more sexy and confident than a white button-down. This tuxedo shirt from Nili Lotan is a nice stand-in for the Marant—or on the less pricey end of the spectrum, this button-down from Everlane.
I paired the button-down with leather jeans, which can be a little too little forward for a first date if you’re wearing them with a risque top; the shirt subdues them, makes them come off as the (very sexy) classics that they are.
I had two dates over the long weekend, and on one of them, I wore this Ulla Johnson top.
I paired them with slightly cropped black jeans. The date went horribly—truly one for the books—but I looked all right.
It’s too cool outside in the evenings to go out without a jacket right now, but I hate when I carefully assemble a look and then my outerwear shlumpifies it. This Iro jacket, which I just acquired at the Net a Porter sale, keeps things snappy. I wore it on the date with the grey top and the black jeans.
On the second date of the weekend, I decided to go more casual,wore this Everlane button-down.
And these R13 grey jeans. That date was kind of fun.
This may look like a clunker of a shoe, but I promise that on it is really quite alluring—even my brother who hates my taste in footwear approved. They dress up jeans nicely.
I bought these heels recently to wear to my mom’s upcoming 80th birthday party, but find that they’re working well for when I’m feeling like dressing things up a little on dates, too. I never thought pumps could be sexy until I tried these on. It’s the ties that do it. Also, they are surprisingly walkable given the height of the heel.
I try to carry a smaller bag on dates; my everyday bag just feels too clunky and workaday. This one fits all the essentials and is pretty cute.