Because you asked: What I wear on dates

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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.

A whole mess of Summer pants

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For whatever reason, I’ve got a lot of requests up my sleeve this week: you all seem to have a lot on your minds. A reader named Kristin wants “General guidance on summer pants—I’m working in the summer for the first time in a long time and am struggling with getting dressed. ” I feel you, Kristin. There are times when I miss working in an office—I desperately miss the spirit of collaboration, and being around other people all day—but I never long for how much I stressed out every morning over what to wear. It used to just destroy me. It doesn’t matter how many clothes you have—and I had a lot—you can always look in your closet and feel like you have nothing to wear. So great basics you can turn to without too much thinking are key. And a good summer trouser counts as one of those. These high-waisted khaki cigarette pants are so damn chic, and inexpensive, and they come in black, too.

A wide-leg pant can be very flattering, and is always office-appropriate.

I’m a big fan of J. Crew’s boyfriend chino; it’s got the just-right amount of slouchiness, and the cut is nice and feminine.

These stovepipe trousers are just a good solid classic cropped option.

linen-blend pant with a deep cuff, a good blue and a nice price.

A good casual Friday grey chino.

From very cool plus-size brand Shegul (which a reader named Becca clued me in to), a very cute pair of tapered trousers.

These have a tuxedo stripe, which is fun.

From Violeta, Mango’s plus-size line, a perfectly snappy pair of  white chinos.

Red trousers are a kick, and really pop with a white button-down.

And why not checked pants?

I just really like the nice clean cut here.

Are you dating?

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Photo by New York street photographer Arthur Leipzig, who was also my mom’s first cousin

It takes a lot of courage and stamina to put yourself out there, and I am frankly not always up for it. I go through periods when I don’t date at all, and periods when I do, and right now I am in an on period. Sometimes it’s impossibly fun—who doesn’t love making out with someone new?—other times, not so much. I’m curious to know how many of you who are single are dating, and how you do it. Are you fixed up by friends? Do you go online or use apps? Have you retained the services of a professional matchmaker? Do you find it a joy or do you view it as a job? I want to hear all.

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About

Kim France

I was born in Houston, Texas in 1964 and have lived in New York City since 1988. I had a long career in magazines, working at Sassy, Elle, New York, and Spin, and in 2000, I founded Lucky magazine, which I edited for ten years.

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