What to Not Wear On a Date…Ha ha ha

Defending all the stuff you’re not supposed to wear on a date because, who died and made you Patti Stanger?


Just a day shy of the one month anniversary of Amelia’s story, How to Dress for a Date, Who What Wear published their version of a similar story that commissioned the help of 11 style bloggers-cum-apparent dating pundits to discuss the clothes that women should not wear on dates.

The 11 opinions offered one example each plus a pithy reason not to wear X. And though it’s certainly not our style to maliciously criticize what one woman might consider her dating treasure — no judgement, just love — it is also not our style to leave, say, socks and sandals or sequins undefended.

But as is always the case, anything one chooses to wear should be underscored by a deep sense of self satisfaction and if that displays itself as comfort or discomfort, harem pants or no pants at all seems irrelevant when considering that which makes you characteristically you.


It’s just…sneakers? No sneakers? (That’s embargo #1), Come on! Never mind the intrinsic benefit of convincing yourself that you’ve successfully fashioned your body as one of those so-low-maintenance-yet-cooler-than-ice broads, if I know anything about the male species, anything at all, it is that they appreciate a woman who can keep pace.

Then there is glitter and there are sequins. Now that you know everything there is to know about those shiny-ass micro discs, you can’t really believe that selling the great awkward-tension-alleviators out in the name of a date is worth the sacrifice. What’s so bad about a sequin anyway? And why are we assuming that the other end of this date can’t handle da glitz? The critic opposite this style said “it looks crazy” but to that I say, “Aaaaand?????”

Next up: turtlenecks, but here’s where I stand — or rather, stood. When I was still swinging across the dating monkey bars, it was deeply important that whoever found himself sitting across from me understood my fundamental emotional dependence on Diane Keaton. And, really, how else can you spell out “You don’t own me” without actually singing it, lest you sport a turtleneck?

The next ban is on flip flops. Though we see her point, what if army pants are involved? What if you’re on a boat? What if the only remedy for your slight-but-lamentable case of webbed toe is to wear flip flops day in and out?

Tracksuits have also been mandated a “no-no” (their phrase, not ours) but tracksuits are awesome. Have you never seen The Royal Tenenbaums? Or met one of those effusive grandparents that seem indigenous to Boca? Does the deceased velour jumpsuit craze of the early aughts mean nothing to you? Never mind the comfort factor, what if you and your date decide to do this? (Click that link.) (Did you click it?) (Are you laughing yet?)

According to the next critic, guys don’t like the way our butts look in high waist jeans but that should just make it our moral obligation to wear them. Why? Because dating is a process of elimination. And if he can’t handle your large sized, rectangular vagina in the pants, he doesn’t deserve the opportunity to jam with your clam in better-looking pants.

Our last comment refutes a bar on socks and sandals because, EARTH TO READER, it’s December and if you want to wear sandals you best be wearing insulated socks tambien. Also, though, sandals and socks look cool, so make like Nike and just do it.

Just remember — process of elimination. Bring him to the ledge and then let him decide to plummet to his death-in-conjunction-with-you or hold on for (a) dear life (of whiskers on kittens, matcha on chia, camaraderie and questionable neck coverings/lambskin condoms.) And this.




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  • marinacasapu

    I can’t say no to a turtleneck even for a first date!

  • Patricia

    I totally agree with you. This is a very funny post!


  • Lauren

    I wore a turtleneck to a first date just last week. I guess this explains the lack of communication. Oh well, he was wearing teal…stripes…

  • Aubrey Green

    I love turtlenecks and I LOVED your paragraph about high waist pants. I’m surprised to hear that they supposedly make our rears look bad though – maybe if you have no ass, or a flat ass…otherwise I think it shows your assets more.

  • Lizzi

    Awful stomach ache before a date…wore sneakers with a cotton dress and trench…told him it was either the sneakers or nothing. He went along with it and I haven’t seen him since. It’s been 6 months…do you think he lost my number? For real. I should call him. I’m calling. #blamingthesneaks

    • Amelia Diamond

      IF it’s the sneakers, then he’s not The One.

  • Jennie

    Jam with your clam…my new favorite phrase.

  • Maggie

    “if he can’t handle your large sized, rectangular vagina in the pants, he doesn’t deserve the opportunity to jam with your clam in better-looking pants.” You have no idea how happy that made me xD

  • =^..^=

    On my next OKCupid first date, I’m going to work the expression “jam with [my] clam” into the conversation. You know, just to see whether he asks me out on a 2nd date…. ;D

    • Ok Cuuuuupid! I met my boyfriend there. Wore a super man-repelling outfit but sadly didn’t get to use “jam with my clam.” You’ve got to do it!

  • Catherine

    Did someone take a picture of my front bottom half when I was wearing high waisted jeans last week, and send it to you? Or do other women have rectangular shaped toe of a camel as well? I love the idea that there are no rules to fashion, no matter the circumstance, no matter the style, no matter the weather. The beauty of fashion is that it’s ever-evolving anyways, isn’t it?

  • kahreeen

    The only one who could get away with wearing a velour tracksuit is J.LO.

  • Souzana Baradie

    Oh my God Leandra I LOveee you, you are so funny!!
    And finally thank you, thank youuu. Because that post on WWW didn’t make any sense!

  • Aline

    Hi there, discovering the blog just today from France. You could just write another post on what to NOT write on a blog and it would be just as hilarious as that one. I’ll be making good progress in english, fashion and self esteem with you. THANKS

  • The important thing is to wear clothes that make you feel good, no matter the occasion…

  • Katja Kozlevčar

    I think the only thing you should not wear on a first date is a skirt/dress that is too short. Everything else can be acceptable according to location and given situation.

  • merli

    You are my new idol

  • Stefanie

    Hahaha! I love this. Maybe because when someone tells me not to do something it only makes me want to do it even more. Especially on a date! If you’re not presenting your most authentic self, what is the point?

  • Thesnobette

    THANK YOU LEANDRA, the future of independent women’s style just got brighter !!!

  • Merrynell

    DYING over “…jam with your clam.” Forgive me for overusing that phrase starting now!

  • Marc Ferraz

    hip, hip, hooray to being yourself!!

  • I’ve worn a turtleneck and high waisted jeans on a date before. Sans large rectangular vagina. I think? He did lose my number though so maybe it wasn’t clam jam enticing.

  • Julie

    haha we should be able to wear whatever we want!

  • MGF

    my oh my
    i just read the 11 no-no things and i definitely remember why I dont read these bloggers

    • Claire

      preach! It all depends on the location and occasion–so if the date is at a park or rock climbing, you’d have to wear sneaker. Ergo–that list become irrelevant.

  • Jessica Beresford

    If you are inclined to wear socks with sandals but suppress the urge on the first date, the other person is going to find out what you’re truly like if it goes well anyway. So why hide it?


  • dupras

    Turtlenecks are one of the sexiest pieces of clothing in the world!! I can’t believe they’re on that list- how silly. A semi-sheer black fitted one with a black bra underneath, skinny jeans, and some cool ass-shoes like the ankle boots in your last post….ooooyeah.


  • Bloomaglow

    You are hilarious. Not only Am I reading this post at work, but also literally lol at work. My favorite ” jam with your clam”

  • Lindsey Cook

    Most of the items on the list I agreed with (more on the basis that they aren’t my style) but I drew the line at high-waisted jeans! They make your butt look weird? Says who? Personally, I think high-waisted jeans – that are fitted, no mom jeans of course – are way more flattering than low-riders and they make my but look pretty good, If I do say so myself.

    Wear what makes you comfortable and confident! That’s the key to success, not banning sequins.

  • Curvily NYC


  • swashi

    Here, here. One should dress a) for oneself and b) for the date, both of which can easily justify all of these and much crazier ensembles. I’m pretty sure by bright red plaid pants are what got my husband to go out with me in the first place (they were my favorites)… Also, I wore them with a turtleneck.

  • Shantae Clarke
  • I love the idea of “no judgement, just love” when it comes to dressing for a date (or for anything). To me, that’s what’s at the core of Man Repeller, and what’s so empowering/inspiring about it: getting dressed each day, not worrying about who approves, but whether it feels true to you.

  • What’s wrong with turtlenecks?? Men are so weird…


  • Alyssaspeaks

    THIS. “Because dating is a process of elimination.” So. Much. Truth. If he can’t take my bag lady outfits he just ain’t worth it.

  • Alex Peak

    I don’t get the recommendation to avoid tennis shoes. I completely do not understand why they recommend high heels instead. Although I would never date someone based on her choice of footwear, if I HAD to choose between a woman wearing tennis shoes and a woman wearing high heels, knowing absolutely nothing else about the women in question, I’d actually probably choose the one in tennis shoes, since I have this preconceived notion that she would be the more likely of the two to appreciate rock music, and since it seems important to me that my significant other and I have overlapping musical tastes. As it turns out, my girlfriend virtually always wears either tennis shoes or boots when we go out because that’s what she likes to wear, and as it turns out, “our” song is “Monkey Gone to Heaven” by the Pixies. I have to agree with the person who wrote this rebuttal piece: ignore the what-not-to-wear list and just wear whatever you feel fits your personality. That’s the only way you’ll ever find a significant other whose personality matches yours.

  • Ruby

    i think my black, tight turtleneck is one of the sexiest pieces i own and one of the simplest. was i the only one to notice the blogger who wrote the no-no on turtlenecks is wearing one in her pic on whowhatwear?

  • Honeybee

    On the first date with my now husband I wore a pair of dangly earrings which I thought made me irresistible (since earrings have that effect…). A couple of months later he said to me that he found long earrings “kind of stupid.” Guess it wasn’t the chandelier earrings, then.