How To Dress for a Date

Without wearing a dress.


I had a date the other night. It went well, whatever, but we all know the most important point of interest regarding that sentence is what did I wear? 

What I wore is the exact outfit a friend told me not to wear: a blue and white striped men’s button down shirt with the front tucked into a pair leather pants, and emerald satin open-toed Stella McCartney shoes with gems that look like Candy Buttons stamped on their heels. Oh, and they have ankle straps.

“Why can’t I wear this?” I asked. I thought I looked pretty good. I was even planning on brushing my hair.

“Because you’re wearing a men’s shirt,” she retorted. “It’s huge. Wear a dress instead.”

Hahahahah. A dress. On a date. That’s so funny. But it actually is, because I had never before even considered wearing a skirt on a date, let alone a one-piece frock. Similarly to what Leandra mused earlier this week, I tend to underdress for occasions that might typically call for a more “dressed-up” wardrobe — especially when it comes to dating.

It’s probably some sort of defense mechanism. If I dress like I didn’t really try, then surely that sends a cavalier attitude to the world like, “Hey, look at me, I’m so cool, I’m wearing pants.” And didn’t Leandra mention in that anterior post that this attitude can often be traced back to some sort of primitive, poignant moment? Maybe in kindergarten I went on a playdate that I can’t seem to remember, and perhaps I showed up in some giant pink confection while my friend Donald Ducked-it in a diaper and tee.

More likely, however, at least in the case of me and my date, is that it boils down to comfort. Dates are awkward. You don’t know where to put your elbows or if your resting face looks too bitchy, and you want to touch your brow to see if it’s furrowing, but then what if he thinks you’re doing some secret signal to a friend in the back of the restaurant that means, “Get me out of here?” One time a guy made us share one burrito (one) and then took my half after I’d eaten two bites. If that doesn’t send a cautionary tale of wearing comfortable-enough clothes to hightail it the fuck out of there, then I don’t know what does.

But dressing “lax” can also help you in the event of a good date. What if you walk through a park? Or if you decide to be all rom-com chic and go for a spin around the old skating rink? If your knees are locked together from a too-tight skirt or wobbly heels, or you can’t lift your arms for fear of a wardrobe malfunction, it’s possible that you’ll regret dressing up.

So while all of that answers what I wore and why I wore it, it doesn’t really help get you dressed, so, let’s get dressed:

Start with pants. You can’t go wrong with leather or its faux counterpart, as no matter what’s happening up top they make your outfit look all the more cool.  I’m also partial to baggier denim, cuffed at the ankle with room for a serious pair of shoes.

Shoes are next. You should really be able to walk. Try the coolest heels you own because you did buy them for a reason after all (though at the moment I can’t stop thinking about simple pumps), but do not pass Go unless you’re sure you can walk at least two blocks without crying and/or vomiting from pain. If you’re all about flats — great. You’ll be that much happier after two glasses of wine.

When it comes to tops I always look for a great oversized button down, regardless of what my friend said. They’re classic and sexy in a Lauren Hutton-esque way. Roll up your sleeves, add some necklaces, bracelets or a cuff and feel like a strong-ass woman.

If you still prefer to take the skirt route in these colder months, opt for an A-Line style, tights and a (maybe?) cropped sweater. The look is pretty but not saccharine and still emanates a vibe that you’ll want to channel when you get the OMG-I’m-nervous jitters.

And that’s that. If this guide seems mind-numbingly simple that’s simply because it should be. Don’t over-think. It’s supposed to be fun. Just be weary of your elbows and we’ll get through this.

Now — if you don’t mind — I need to hear some fashion-fostered dating stories, so, please, indulge me.

Image via Marie Claire Russia

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  • emilyannestyle

    DAMMIT why did you have to show me that Isabel Marant sweater? Of all holy things on ShopBop, I have fallen in love with a black sweater.

    In other news, I haven’t been on a “real” date in years. (Matrimony will do that to ya.) But my go-to for when we go out is a baggy-ass boyfriend jean OR a colored denim with a simple blousy top. I always let the accessories take the front seat.


  • How does one split a burrito. To be honest, I’m always looking for another after I down my first. When asked the other day what I’d miss most about California if I were to go out of state for college, I answered “the burritos.” (Can I get a ‘hell yeah’ for El Farolito in the Mission district of SF!).

    As for your dating outfit suggestions, I think these items could be valid in so many situations! They all rock, and I know the awesome Stella McCartney shoes you speak of — definitely that whole Candy Dots thing. A men’s button down is practically a uniform at this point. Comfort at all times, esp. when you gotta run away from men who even think that burritos are for sharing.

    • Charlotte Fassler

      Being far from California Mexican food never gets easy.

      • Even the changes in burrito — and Mexican food styles — within California is hard. I remember a few years back when we moved away from the Bay Area and I think I cried biting in to a southern California burrito. They’re great and delicious now, though! Other states claim great burritos and they are almost laughable post-bite. (sorry, this is a passionate topic).

    • Coco Ho

      I just spilt a burrito for lunch today. That’s why i’m having a muffin..

  • I am with you. It’s all about comfort.
    Can we take a second to address what MEN wear out? So many men think that being fashionable makes people think they are gay. In reality, a well-dressed man is truly impressive. If more straight men knew how to dress, there would be a lot more penetration going down.

    • Cass

      Seriously. And can we start with at least buying the right sizes??!? Baggy denim on men is just not attractive. If you can’t buy clothes that fit you, I’m out. Immediately.

      • Devin

        I most whole heartedly agree. Baggy denim, slacks, and shirts are a resounding “no”. For fall fashion a nice long sleeve sweater/shirt, the right fitted darker denim jeans, and some ‘cool’ shoes will do. Give me a guy with that, complete with a beard/scruff and watch out.

  • EmmaM147

    Lovely post! Very helpful!

    Emma x

  • sonaliraq

    I showed up for my first date with a guy back in January after an intense sweaty dance class with no makeup on wearing exercise clothes and sneakers. We’ve been together ever since.

    • Philosopher

      This is my exact story, I shit you not, except four years ago. And we just got engaged. He recently told me he thought I was so daring for not caring.

  • Anna Jezewska

    i dont know what can be more sexy ,sophisticated and cool than a woman in men’s shirt it alo comes with ease.his got buttons to play with,you dont have to worry about spanx.that and a confidence powerful combo

  • CharlotteC

    I always pretend considering at first to wear one of those few dresses we buy for “special occasions” (and which has obviously never been worn since, huh?), but always end up wearing something i’m comfortable in, even if it can involve dress or skirt. I just don’t feel super chilled with an over sexy look with a not very subtil subtitle “tonightimplanningongettingsomebaby” 😀
    Bisous from rainy Paris!

  • CharlotteC

    PS: a guy who steals your food is DEFINITELY a deal breaker… Right?

    • EMR

      TOTAL Deal breaker. That, and a guy who orders for me without my permission.

      • EllMorrow

        That and the guy who wants to spoon-feed you in restaurants, why is that a thing? It is not romantic and I am certain I can eat without pretending an aeroplane is involved.

  • Annie’s Fashion Sauce

    In my humble yet entirely pompous opinion, your friend…was downright wrong. I consider a button-down and pants (preferably leather, or something masquerading as leather) to be the perfect combination for a date. There’s something to be said for balance, and for leaving a lot to the imagination. Leather says “I’m fun” (and, if you’re doing it right, “I’m stylish”), and pairing leather with something classic (the term I will use in place of “masculine”), like an oversized button-down, prevents your leather from saying “I’m a try-hard who takes herself super cereal.” It’s all about the contrast. Because you should arrive to a date looking like you’ve put effort into your appearance, but you don’t want your outfit to look so over-thought that you seem desperate to add a big diamond ring to that ensemble. I also find it very important that you mentioned cropped SWEATERS as opposed to the traditional crop-top. Everyone wants to look at least somewhat sexy on a date…right? A cropped sweater that reveals nothing but the smallest sliver of skin is the key ingredient to subtle sexiness. In short, I’ve scored more boys in a shirt buttoned up to my chin than I ever did during those five minutes in college when I tried to let my cleavage do all the talking. And as for dresses…I feel no need to even acknowledge dresses. Dresses. Ha!

  • Lis

    The only advice that I would give is to never wear super high heels on the first date. It always feels awkward (probably because I am 1.80m even without heels, and towering over men is not really attractive.)

  • Lilli

    I put a lot of thought into getting dressed for a date so why don’t boys? i have a phobia of thongs aka flip flops aka the ugliest things ever. So whenever I arrive at a date i check to make sure they are not wearing them especially if they are paired with jeans…. because if its cold enough to wear jeans, please put some enclosed shoes on those toes. AAAnd if they are wearing thongs I literally cannot see a future past a 5 minute chat

  • Annette

    First of all I have to tell you that when I was in NYC for Fashion week, everywhere I turned or spoke to happened to “know” you in some form or another, raving about how awesome ManRepeller (You) are – Maybe this is what happens when you hang out too much on the upper east side 🙂 So I’m sure your leather pants and button down were fine – at the end of the day someone’s not going to turn the other way because they didn’t like your shoes!! Beautifully written article, hopefully you’ll give us a follow up 😉


  • Thamsa

    I always opt for the clothing that makes me feel the least self-conscious. So, no skirts or too high heels.Though, my friends might frown at me for saying that because I’ve always been a bit too casual on dates, but I figured that if the guy asked me out when I wasn’t glammed up, my personality and good humour must trump my appearance….

  • Brett

    I work as a personal stylist, which I have to admit has been quite a deterrent for men in which I’m interested. I once dated a guy who had such an easygoing style, but could never get ready before going out with me before I approved (mostly picked) his outfits first. Obviously that relationship didn’t work out. I try to be polite when dates ask me about their outfits, but once a man showed up with ripped jeans, a button down with a tie, and the wrong Vans; he about shat his pants when he learned what I do for a living. And I about shat mine when he asked if I thought his outfit was okay.

  • All about comfort!

  • fbcreations

    you couldn’t be more right, even with the second option of the skirt and the flats, it’s the perfect kick ass girl, rock meets feminine with a twist of fashion.

  • I never know what to wear for a first date and find it fascinating that a guy will show up looking like they just rolled out of bed while I spent hours picking out a top that reveals just the right amount of cleavage without being too slutty.

    I’ve concluded that it doesn’t really matter what you put on they won’t really notice anyway.

  • I love this post! I am married but we still go on dates 😀 One of my favorite things to wear on a date with my husband is leather pants, one of his button up shirts, great pair of heels, and messy unbrushed beach wavy hair. I love stealing his clothes haha. I don’t know if he loves me wearing his clothes but I feel sexy in one of his button ups 😉

    xoxo J
    (Interior Design/Fashion)

  • Aubrey Green

    I’m a pants girl, so I would personally wear pants. I also love heels, so I would wear heel. I think a button down is perfect, but also just a white t-shirt with a blazer is great too.

  • Astrid

    Did you read the post and the British Vogue article Natalie Joos did on this subject? It basically says the exact opposite of what you’re saying, but I like your version better. I thought Natalie’s was so depressing! According to her, guys really only want to see skin and legs. She wore this super sexy and on point pant and cut out top with Pigalles combination once to a date and the guy still said she should have put on a dress. Man, and I thought guys could appreciate some individuality in girls! Now my guy likes me in my Marant stuff luckily but I’m not sure it’s the same for every guy … shame!

  • You are my love in reading! Love this blog much because of your awesomeness in writing.

    Just 5 days left to enter this giveaway to win £150 voucher @SoJeansUK | Fashiongentrix

  • Devin

    I’ve always loved reading through your blog posts, but recently I’ve been obsessed. Okay. Dating. I come from a date obsessed community. Mormon community. Date, date, date. But as of late the word ‘date’ is not the word of choice–guys prefer ‘hang out’. So, with that tone I agree that a little laid back on the wardrobe is the way to go. Pants–skinnies, leggings (with tunic/oversized button up of course, don’t want no butts or you-know-what’s in the front), or semi-nice slack-like bottoms. I also agree on the leather, it just takes a boring outfit to the next level. Top–what ever you’re comfortable with, I tend to go towards a semi-sexy button-up as well. Now for the shoes, when it comes to deciding about heels be sure you know you’re not going to be taller than the date, because let’s be honest, that would be almost as mean as “sharing” a burrito (who does that?). Dresses and skirts call for special date occasions such as: fancy restaurant, movie, or lovely ball/dance sort of atmosphere.

  • Everythingisnormal

    This is what I am finding: cool men like cool women. It’s that simple.

    So when I try to pull off the sexy skin tight black dress thing, I actually get zero attention.

    When I dawn a blazer with a white silk shirt and single sole pumps, meanwhile, I get 3 different cars stopping *in the street* to get my number.

    Or when I cover up, wear a skirt, black tights, ankle boots, a sweater and a hip-accenting coat, almost every guy I run into mentions I look nice. (The Parisian dude I was dating for a split second totally swooned over that number. He asked me if I “dressed like a Parisian girl” that day to turn him on.)

    Let it be known, at 5’0 and with more than ample booty, I am not a modelesque stunner. I also have obscenely short asymmetrical hair that I think would make the average bro’s testicles recede.

    Truth: if you go for looking like a badass as opposed to a fantasy, you win. Being a badass was their fantasy all along.

    (You’re not a basic bitch, so why present yourself as such? If he wants something other than what you are bringing to the table–be it opulence, femininity, androgyny, whatever–then fuuuuuck him. Date someone who appreciates you looking and feeling the most like you)

    ***Sorry this is heteronormative btw

    • Maha

      love this! totally agree that men are interested in more relaxed women! whenever i’m wearing minimal makeup and/or an all black ensemble, men seem a lot more interested.. strange but true!

      • Adrianna Grężak

        I’ve had a lot of close male friends and acquaintances over the years. They have all said that things like make up makes them cringe because they don’t want a high maintenance girlfriend. The logic is that if you’re so concerned about physical looks, you’re going to be overly concerned about other things.

  • jacqui

    you CANNOT wear baggy jeans on a date regardless of how well they show off your heels. men hate baggy jeans

    • Not mine!

      Besides, it’s like a hidden surprise of a great bootay underneath (your pants are playing sexy hardball with your man FOR you. Magic).

  • Chloe

    I do not wear pants so it’s always the classic combination of black turtleneck and statement skirt, ie a floor length chiffon crimson skirt or a mini skirt embellished with sequins and so on. Topped off with an oversize coat thrown over the shoulders and modest flats to maintain balance. And it’s true as some others said, that overexposure does not guarantee sexy. I’ve turned more heads when I’m in a floor sweeping skirt buttoned all the way up then the rest of thighs/breasts-flaunting girls all together.

  • pauline

    totally agree with you

  • I will always go the pants route– because that’s basically what I do everyday. I’ve already mastered the “rock the pants” look, so I’ll reserve the skirts/dresses for some casual Netflix date.

    Your Friend, Jess

  • I tend to dress down for occasions myself. I like to set the bar low so when I actually do give it my all not only will people be surprised but so will my confidence from my manufactured style praise.

  • Dani Shapiro

    On my first date with my now boyfriend, I was absolutely determined not to look like I was “trying too hard.” I went over the top in the opposite direction in a long-sleeved striped tee, way-too-short cutoffs (I thought it looked casual at the time… looking back, it was a damn bold move to show that much leg), and white converse. I threw on a subtle statement necklace (oximoron?) and called it a day…

    Months later, we discussed this outfit. His one major comment? “I was so intimidated by your outfit! It was hard to look you in the eyes when your entire legs were just exposed, staring at me like that.” #Thankyouverymuch.

  • littlegirlblue

    I have a date tomorrow and I saw this was today’s post (yessss) and what you said to wear is exactly what I was planning to wear (double yesssss)

  • Had a date with my husband on Tuesday – because I suggested we tried going out every once in a while (a gladly accepted suggestion if there ever was one). I planned on wearing a skirt (brown woollen knee-length skirt with huge beige dots) and a purple cardigan with a revealing purple top underneath. Then the winter came, so I wore my favorite skinny jeans (grey) with low black boots, a hot pink longsleeve (revealing my best 2 … selling points?) and a huge black cardigan. Men’s. I need to have my hair cut to be able to show my ear cuffs next time 🙂



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  • yv

    This guy I dated for 3 months couldn’t help commenting on my dressing all the time. For our first date he actually thought I didnt like him very much because I was wearing a denim shirt (but with a short skirt! come on!) and I found myself changing my style to cater to his likings for tighter/ sexier options.

    I am so done with that. Buh-bye.

  • l’oliphant

    Comfort!!! for a date you just need to think about this!

  • Comfort above all when it comes to dating (no sweatpants lool) just because you don’t know what he/she planned for the day. On the first date you still don’t know much about each other, so there’s nothing wrong with playing safe 🙂


  • Adrianna Grężak

    I met my boyfriend in a tight sequined dress on New Years Eve 2011. I distinctly remember saying “this is the complete opposite of my wardrobe, I’m wearing this as a joke.”
    “What do you normally wear”
    “What you’re wearing.” He was wearing jeans and a plaid shirt.

    We started off as friends so I didn’t put a lot of thought into my outfits. I even wore a sweatshirt one Friday night, something normally allotted for Couch Time. He once joked it was weeks before he saw any skin, because it was winter and I wore a lot of sweaters.

  • CDJ

    The only time I have ever resented the amount of daylight summer brings is when I went on an early dinner date followed by A GAME OF CATCH IN SOME RANDOM PARK. I’m sorry, I am not anywhere close to athletic, nor do I think it’s fun to play wifflle ball with a stranger. I am thankful, however, that I chose a laid back outfit for the occasion (shorts, long tank, loose cardigan, sandals), so I could, you know, play ball. That was the only date we went on.

  • Pilou

    soooo true
    exactly the same for me yesterday, I could have climb a building with my furry camo parka + corduroy jeans + leather/camel Vans.
    Forearms and smile are the killers. Just show them, and I dare to think it s enough 😉

  • sophie

    Amelia I love this. And you. I really hoped that I “Donald ducked” it to at least one playdate in pre-school.

  • dupras

    My last first date outfit was a black turtle neck (even though most guys would say they hate them). I’ve found a semi sheer one with a spaghetti tank underneath (or a bralette if I’m feeling racy and/or don’t give a damn how the date turns out) to be comfortable and less-is-more sexy. Paired with black skinnies (or said A line skirt) and of course, bad ass shoes which should always be in the equation no matter what. When my current boyfriend complimented my “rue colette” after our first date I knew there’d be many more dates to wardrobe 🙂

  • Camila Santa Maria

    I am crazy about fashion and I’m currently dating a very relaxed guy. He is pretty awesome, incredibly smart, cute, and a perfect gentleman. And the fact that I like him a lot means that I drive myself crazy whenever thinking about outfits for our dates. (What does one wear for a dinner at a fancy restaurant followed by a drink at a shabby (but great) music bar downtown?) In these cases I practically stalk one of my best friends who is a fashion student. Sometimes I even send snapshots of my outfit for her to approve. One time I wore basically the opposite of what she sugested but I felt so pretty and confident that I think the date succeded, mostly because I could really focus on being in the moment instead of fussing about my clothes.

    One point I’d like to make: although I absolutely love skinny leather pants, they are incredibly tricky to take off, so ladies keep that in mind when planning for a date… (This is one of the reasons I believe it is great for first dates, second and all… But going forward you might want to switch strategies…)

  • JiaoJiao

    I just had a conversation about burritos with a friend and we were talking about how while at Chipotle, we find ourselves always being served less beans, rice, meat, etc., than the males before or after us! Just because I am a female does not mean I can not eat just as much as the boys ahead of me. We all like to eat and I especially like to eat my own burrito!

    I’m not sure who your friend is and I’m sure she had the best intentions while telling you to not wear a men’s button down, but a dress and even a skirt is so predictable! When every man thinks of a date with a women, he imagines a dress with some earrings and a necklace. If you think you look great and comfortable in what you want to wear (and your outfit sounds very appealing!!!), then you should definitely wear that! How else are you going to introduce him to your man-repelling-fashionable taste?

  • Alexandra H.

    The beginning months of my relationship with my boyfriend of 31/2 years he wanted to take me out on our real first date. I was so excited but when it got down to what to wear on an October brisk evening I was clueless. We live in New Jersey, and only 15 minutes from New York City. What better place to explore and have romantic night? The city eveywhere you look theres always someone walking down the street like a runway and you can’t help but want to look fashionable too! So you can imagine what my room looked like trying to rumage through my closet. After trying on dresses, skirts and heels I opted for skinny black jeans, a flowy blue blouse and a black blazer. I was so indecisive about my footwear but at the end I knew I made the right decison. Why feel uncomfortable when you can still look great and walk around without stumbling. Pants and nice flats still can be sexy!!!

  • tesslovesloo

    I typically overfancy even when I puposely try to under fancicfye. I have been on over 50 first dates this year, while some are a waste of the laundry detergent and lip gloss, and others just plain suck. Regardless of the outcome, a date is always a good opportunity to step out and practice looking good and acting better, while learning a bit more mannology.


  • Nika

    Do not ever dress or act a certain way for anyone else but y o u.

  • Cute post! I still remember what I wore on my first date with my boyfriend of 8(!) years now; a pair of skinny jeans a daffy duck t-shirt with a funny quote and a pair of embellished loafers. And he complimented me on what I was wearing! Definitely not something I would wear right now, I’d probably consider something similar to your suggestions, so thanks for that, just in that unexpected case where I’ll get back on the dating market 😉

    xoxo Iris


  • JReneeOK

    I recently wore my kick ass, green velvet Stubbs and Wooton loafers with an embroidered Dollar sign on them, on a second date and the Baboon insulted them. Commenting twice, I finally asked why he took such interest in my shoes and he told me that he “was just trying to find something nice to say about them.” I am all about making myself feel sexy, cool and comfortable, if the guy just doesn’t get it, then he certainly is not gonna “get” me.

  • Camila Santa Maria

    I am crazy about fashion and I’m currently dating a very relaxed guy. He is pretty awesome, incredibly smart, cute, and a perfect gentleman. And the fact that I like him a lot means that I drive myself crazy whenever thinking about outfits for our dates. (What does one wear for a dinner at a fancy restaurant followed by a drink at a shabby (but great) music bar downtown?) In these cases I practically stalk one of my best friends who is a fashion student. Sometimes I even send snapshots of my outfit for her to approve. One time I wore basically the opposite of what she sugested but I felt so pretty and confident that I think the date succeded, mostly because I could really focus on being in the moment instead of fussing about my clothes.

    One point I’d like to make: although I absolutely love skinny leather pants, they are incredibly tricky to take off, so ladies keep that in mind when planning for a date… (This is one of the reasons I believe it is great for first dates, second and all… But going forward you might want to switch strategies…)

  • Nic

    The whole rom com ready outfit advice was so needed a month ago! I chose a skirt and leather jacket combo but we ended up spontaneously going longboarding. Needless to say I needed to change and my date had to wait for me to slip into jeans and a more movement-friendly jacket.

  • Love it all.

    Micah xx

  • Amelie

    As always, I love the stylings for this!

    The Neon Guava

  • I have the same problem of underdressing for some occasions. Sometimes I feel like I should up the dressing game but I really don’t feel comfortable wearing a dress unless its very casual or to a club. 😛

  • Maui Mendoza

    Last week I made a terrible mistake of actually “consulting” a guy’s blog on what to wear. He kept on going about a girl should always be fully made-up (hair and makeup!), always wear heels, never wear sneakers, and wear tight clothes. Idiot that I am, I actually took his advice(skipped the heels tho). By Friday I felt super depressed. I didn’t feel like me anymore. After a teary Sunday night, I resolved never to look at that horrid blog again.

  • Nicole

    Uhhhh… leather pants.. just brings to mind that date Ross went on and couldn’t get his pants back on. (F.R.I.E.N.D.S = best forever! FBF). Ever since then I’ve been afraid of leather pants and I am still unconvinced they’re a good choice for a date. I hope on your next date you get to eat a whole burrito.

  • Eleanor Rigby

    Great idea. I noticed that I always wear the same outfit if it’s a date or a regular day. Last date, I pulled off an Equipment shirt that I tucked in some Acne jeansand heels, with a camel top coat or a trench. To be honest, you just need to pull off what you are comfortable in. PS: showing two much skin always attracted the weirdest men. Not recommended in my book for a date.

  • the coattail effect

    I would go with a soft sweater, skinny jeans and ballet flats…that means I can go comfy without showing up in my pajamas

  • Rebecca

    erugh who wants to try too hard on a date? ERUGH!