Thursday 14th December 2017
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Because you asked: What I wear on dates

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.

Posted on May 31st, 2017 48 Comments

48 Responses

  1. Dana D says:

    Excellent date choices. And the options here work well for many body types, no?

    Love that you are including different size ranges in your posts.

  2. Ann says:

    I’m not sure if you said before, or maybe you don’t want to say, but how are you getting all these dates! I read the comments on the dating post to try to pick up tips and ended up a little dispirited. Forgive me for being nosy, but I am in awe of your dating prowess!

    And your date outfits look great — I love those shoe/boots.

  3. KimFrance says:

    I hired a professional matchmaker and also employ Tinder and Bumble.

  4. Tami says:

    I once told my younger sister, who is 43, a single mom and dating in NYC, that if should my marriage should end that I don’t think I’d have the emotional wherewithal and the clothes to date. She told me, “Yes you would. You would throw on a pair of leather pants, a cute top, sexy shoes and put yourself out there.” You and my sister are on on the same page!

  5. deana says:

    I love those open toe shoe/boots so much. I’m always looking for a cool/sexy/comfortable shoe. Anybody know of a more reasonably priced alternative? I have three teenagers (which equals three college tuitions coming up), so my days of super expensive full priced shoes are over (if they ever were).

  6. elizabeth says:

    very cute outfits, but I came to the comments looking for some details re. the terrible date!

    • KimFrance says:

      There will be a chapter on my dating life in the book. I’m not sure this guy will make it in. I’ll give you one detail: we met in the lobby of the Ludlow Hotel, because we were to have dinner in their restaurant. My first sight of him was him sitting on a sofa, with his (large) stomach hanging out of his shirt. It went downhill from there.

  7. Jennifer says:

    Thanks for this post! I was among those who’d requested it–much appreciated. As someone who’s been online dating in New York for the past six years, I’m always curious about outfit formulas for first dates. Best of luck out there, Kim!

  8. Jessie says:

    Very useful post! I’m married, but these are great suggestions for making my date night outfits a little sexier and cooler.

  9. Viajera says:

    The Ulla top is really lovely. Buy more of them!

  10. AmyM says:

    Surely I can’t be the only one dying for a few details as to why the bad date was one for the books (unless you’re going to actually include it *in* your book, in which case, I’ll be patient). Also, that’s my favorite of the date outfits.

  11. c.w. says:

    I really do love that Iro jacket (said same on your Instagram).

    Such fun to see these outfits so thank you for sharing. I think your choices are terrific. Cool girl cazh…approachable, yet independent and not at all covfefe.

  12. Jana says:

    Love the clothes, as usual…But God, I’m so codependent, I was more excited to learn about your dates (the good ones, anyway).

    Always pulling for you, stranger friend…

    • KimFrance says:

      The first good one—the leather pants date—was with an astonishingly handsome, very charming man who I of course had to invite home and make out wildly with for hours. Never heard from him again. So now I’m instituting a no-going-upstairs-on-the-first-date rule. Should have learned that lesson by now, but better late than never. Second good date was with a very nice, smart, and cute attorney who I’m going out with again next week so we shall see.

      • Jana says:

        OH! I didn’t mean you owed me/us more info on your dates–good or bad. I just meant I was excited to hear that you had some good ones.

        That said, I ain’t gonna turn down the details. I’m excited about your second date next week–good luck and have fun!…And you still may hear from the Leather Pants Date. Men can be weird with the call back.

        Btw, I hear you about the “upstairs/first date rule.” But then again,there’s nothing wrong with a little wild making out or more. A girl has needs…

        • Heather says:

          I’m impressed with your restraint – I would’ve done more than make out!! 🙂 yeah, I’m bad about that…. but live and learn…

          That said, I’m also excited to hear about your dating experiences (can’t wait for your book), and these are great outfits. I think leather pants are an excellent choice. Sexy but also badass. The Ulla top is really cute.

      • Dana says:

        My favorite relationship I’ve ever been in started out like the one with the handsome man. We had a great time, got hot-n-heavy, and then I didn’t hear from him for about a month. I was complaining to my friend about and she advised that maybe something came up. It had, his father was sick and he had to go to Cali for the month. So maybe he’ll call. Or the attorney will sweep you off your feet. I’m rooting for you. These updates are giving me courage to get out there.

      • Mimi says:

        Aren’t rules made to be broken? A good friend of mine slept with a guy on their first date 15 years ago. He’d been a Fulbright scholar, lived in Paris and had a home in St. Tropez. Ten years ago they got married. There are parts of this fairy tale that are less than wonderful (his 4 awful adult children, for example) but my point is having sex right away did not hurt the growth or longevity of their relationship.

  13. Francine says:

    LOVE all your choices (pricey though they are), especially the leather jeans. I’m sure you looked dreamy.

    Crazy that we’re hanging on your every word about the dates. I’m so excited for you. Hope the attorney knows his good fortune and exceeds your expectations friend!

    • deana says:

      I always love the idea of leather jeans but not the price and how they look on my thighs, so I do coated denim jeans. I have a great pair from old navy from a few years back. DL1961 does heavier, more substantial coated denim. Obviously pricier than Old Navy, but way cheaper than leather.

  14. Erin says:

    That Iro jacket is next level.
    I really love this little community of yours- it’s the best of women.

  15. Erica says:

    Your style is just impeccable and those guys are lucky to go out with such a smart stylish woman! Love your posts!

  16. MariaO says:

    I’ll have you know that this post resulted in (1) spending time looking at various Iro jackets on the internet and (2) buying one (on sale! but not the one you show, a rather ridiculously lovely superfuzzy boucle one).

    I’m not dating, but I wanted a cool jacket. Thanks!

  17. Heather says:

    Kim, I’m super curious that you’re using such a range of possibilities (from professional matchmaker to Tindr). If you feel like answering, are you finding significant differences between the men you’re meeting through these various platforms? There are so many stereotypes, ie guys on the free sites only want hookups while the guys on Match are actually looking for relationships — but in my experience, guys tend to have profiles on multiple sites just to increase their exposure, so it doesn’t seem to matter.

    • KimFrance says:

      Well all of the men I’ve met have been very different, but so far I can’t say I’ve seen a real difference across platforms.

      • Dina says:

        I have heard from quite a few people (including a matchmaker directly) that many matchmakers now swipe Bumble and Tinder to find matches for their clients – that could be why you’re not seeing a major difference.

  18. Heather says:

    I’m curious re awful dates like the belly-man described above. Back in my years of internet dating I met a wide range of individuals, but there was only one (thank god) who was an immediate, absolute no. I did stay and have a drink with him (praying no one I knew would walk in), because walkinh out just seemed too cruel. Plus Id already put on makeup etc. What have otgers done?

  19. Lisa says:

    Fantastic outfits! I’d date you and I’m deeply heterosexual and happily married for the second time:). Not that you need my approval, but, it’s given with lots of confetti.

  20. Susie Hwang says:

    Shopping kismet! I found the R13 skinny boy jeans on sale on a Canadian website. Do they run true to size? (All they’ve got left is a 25. I’m usually a 0/2, no butt and thighs but ample waist squish.) Your sizing advice very deeply appreciated.

    • KimFrance says:

      Sizing on R13 is a little all over the place. Mostly it’s true, but every once in a while, something runs really small. Congratulations on your score!

      • Susie says:

        Thank you. Just discovered your instagram. Crushing so hard on your style, sistah!

  21. Rae says:

    This is off topic and late to the conversation but I have been thinking about it since the “Are you Dating?” discussion and think it would be an interesting follow-up discussion. Many commenters mentioned that they are discouraged because men their age all want to date 25 year olds. But do any of you know 45 year old men with 20 something gfs or wives? Did any of you date men in their 40’s and 50’s when you were 25?

    I have a pretty big circle of friends, have lived in a number of different cities on the east coast and can’t think of any friends who actually lived out this fantasy! I do have two friends married to older men. One marriage has an 11 year age gap, the other 15 years. But both married in their 20’s when their partners were men in their 30’s.

    Does this fantasy that many men clearly harbor exist outside of Hollywood and the White House?

    • Mae says:

      Excellent points, Rae.

      My husband has three long-time buddies in their mid-50’s who are currently divorced and dating. Of course, each of them wants to get laid right away — they’ve just come off a looooong dry spell with their now ex-wife — but all are looking for someone around their own age. A man in his fifties likely has children (or nieces and nephews) in their twenties and thirties. That usually changes their perspective from fantasy to reality.

      And I’ve never personally known a woman in her twenties who actively sought much older men. I mean, why bother? Healthy men in their twenties are adorable, fun, and LOOKING FOR YOU, TOO, when you’re a woman in your twenties! If you don’t like that vibe, there’s no pleasing you.

      The rich-old-coot-with-the-sexy-young-wife/girlfriend is mostly t.v. bullshit (with Trump being the worst offender). It also happens to be a harmful fantasy that is the root of sexual harassment in the workplace. I’ve witnessed it everywhere I’ve ever worked over the past 30+ years (in corporate finance). Women in their twenties are frequently the targets of older creeps in the office. Doesn’t exactly provide a positive image of May-December romances.

      All you ladies who are dating strangers, have fun, but do be careful.

      Love, Auntie Mae