Overthinking Underdressing

Or is under-thinking overdressing?


Is it better to be overdressed or underdressed? I ask because I have historically empathized with she who hails from the latter group and as such, recently determined that the very question above informs more about my style than I may have initially believed it to.

I think I’m becoming casual-to-a-fault. My aesthetic leans more toward Narciso than it does Nike, and recently a close friend named Claire has been making the same joke, without fail, every time I walk into room where a celebratory, slightly-but-not-quite formal is being held: “Oh! Ripped jeans! For a change!”

You’d think the punchline would wear off after being repeated so many times but it doesn’t. This is probably because the only thing worse than a recurring joke is a recurring, out-of-place outfit.

At my cousins wedding the summer before last, I was almost asked to leave on the account of my pant-not-so-suit. For visual reference the pants in question were eggshell-colored charmeuse crepe palazzos; they hit the floor as spectacularly as they buttoned at my waist, and with them I wore a white silk t-shirt, gold choker and layered a light blue double breasted linen blazer over my shoulders.

“It’s black tie!,” my aunt yelled at me in her foreign accent. My mother, father, great aunt and a red headed girl I don’t know looked on while she assessed the visual damage I would inevitably cause to the bridal party, of which, mind you, I was not even a member. And to this day, every time I see that aunt, she reminds me that I wore pants to her daughter’s wedding.

Did I find it disrespectful? Absolutely not. Could I see where she was coming from? Indeed: Squareville, USA.

But more interesting than the actual clothes and the responses they continue to elicit is perhaps why I dress the way I do; why, when I see a pair of ripped jeans, the internal amicability alarm sets off and I am almost immediately wooed. Furthermore, no matter how beautiful the gown, how perfect the fit, how elegant I feel, I am never as comfortable when torn away from the clothes that make me, me.

This seems counterintuitive when considering the “identities” I so often speak of assuming via clothing (The Lady, or The French Girl, for example), but I’m going to trace this handicap back to a primitive, savage time: The Era of Bat Mitzvahs.

When one classmate of mine was turning her Holy Twelve, her parents threw a party at a JCC in New Jersey. These particular parties called for dresses, but style maverick that I was, I forewent the dress for a pair of green ill-fit trousers, a black shirt with white Mongolian faux fur trim and a pair of knee-high wedge boots that were a little small on me but still the most magical possession I owned, what with their leather leaves embroidered on the shoes’ calves.

It took my mom and me over an hour to get those boots on my feet. At the end I thought it was totally worth it, but when I got to the party, all the other kids were in t-shirts and jeans. This was a jungle gym party that had no place for embroidered leather. Nor did it for my hairpins. Everyone looked so comfortable and cool in their easy outfits that allowed for child’s play and here I was in itchy trim. I felt like such a fool.

So you know what I did? I disappeared into a corner to take off the shoes that stole an hour of my life and tucked the fur trim into my blouse while I wished I was in jeans.

Twelve years later I still can’t shake that night off. Why didn’t I just own how I looked? Why did it make me so uncomfortable? Is it possible that at just 12 years old, I’d already culled an idea about the implications tethered to being over vs. underdressed? Did I really know that to be the former meant you’d tried too hard and therefore to be the latter effectively made you Kate Moss — and effortlessly, at that?

I’m not quite sure. But it is possible that for everyone who’s tickled by getting overdressed or perhaps similarly, by looking like they don’t even know they’re dressed, a congruous story floats through their past. So maybe I’ll ask again — is it better to be overdressed or underdressed?

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  • Hannah

    It is better to be yourself-that package may be an underdressed or an overdressed one.

  • I love the Vogue UK picture, it’s an underdressed outfit I would love to wear.

    Mafalda ❤

  • There’s a novel by Milan Kundera, Immortality, in which he portrays 2 sisters: one of them tries to find the meaning of life by accumulating content (things, experiences, emotions … everything), the other one tries to do away with content she deems unnecessary to see what remains.
    Maybe, just maybe, most of us can be described by means of combination of these two opposite tendencies? Like: 17% of my time, I love to overdress, 81 % of my time I need to underdress and the rest of my time I am just damn undecided? (possibly this would describe me .. I went to my Confirmation (Lutheran) as well as to my prom severely, visibly underdressed and didn’t mind it at all, but I don’t like to do that anymore (age, wisdom 🙂 to such a great degree, just being on the verge of it suffices)

  • Fashion Follows Her

    I think underdressed with a good splash of bold accessories… http://fashionfollowsher.com/

  • Cla

    Really I couldn’t say. I like to dress up, even to go to the bar, I usually wear something fancy when everyone is in jeans and boots. And so what ? I feel comfortable.
    It’s just about being comfortable in your clothes. I like to go to parties with ripped skinny jeans too, maybe I’m just weird and I do the total opposite of what people expect from me. But who cares anyway !

    • Devin

      I hear ya. I’m more comfortable in what some may consider “overdressed” attire that I define as me.

  • Lynn

    I would choose over vs. underdressed any day of the week. When I’m over dressed I own it and I’m like “look at these losers in their jeans while I’m rocking sequins and tulle” but when under dressed I AM THAT LOSER.

    • Amber Nefertari

      I couldn’t have said this better LOL!

  • pinkschmink

    I live by the motto ‘never knowingly underdressed’. But I suspect that is in large part because I am a ‘winter’ person. I like layers, and sumptuous fabrics, and plentiful accessorising opportunities. Summer (and all its associated near-nudity) is the scariest time of year for me. And yes, I am that girl who turns up in a cocktail dress to the party where everyone else is in jeans. Always have been, always will be, and I’m cool with that.

  • Kate

    This is an interesting debate that I think would be won with the much-fantasized-about-but-almost-totally-unatainable over-dressed outfit that looks effortless, thus making it FEEL “underdressed”—if only that look were easily achieved.

    As a general rule, I just throw my giant, (faux) fur vest over everything (I’m from Canada, so fur, faux or otherwise, is almost always appropriate) and hope for the best.

  • Chloe

    Hmmm… I guess I’m most comfortable in a some sort of juxtaposition of casual and formal. I love ripped jeans with silk or a delicate lace… A favorite outfit of memory was for the after-party of a friend’s wedding. I had worn a black silk, full, floor length skirt with a metallic silk blouse to the ceremony. After the reception, I kicked off the Ferragamo pumps and laced up my doc marten oxfords for drinks with old friends. I kinda wanna wear that one again!

  • bretonstripes

    for me, overdressed, always.

    sidenote, I very, incredibly rarely laugh for real at anything net-side. But this was a different story and had me recounting the paragraph to the room:

    Could I see where she was coming from? Indeed: Squareville, USA.

    Leandra, you the best.

  • Mira

    I’m not sure whether it was this particular day that cemented my belief in underdressing or was it just a collection of such moments but either way this is what I remember best: as a kid I used to beg my mother to let me wear pretty dresses and she was always against it, telling me how shorts & t-shirts are so much more practical and it doesn’t matter if I get dirty in them; so when I was 11 or 12 and had to pick an outfit myself for this end-of-school-year-mini-party I went for the probably dressiest thing I owned. It was a black realy weird looking, maybe 50’s inspired puff sleve black dress with white coffee beans/ polka dots and from what I remember some grungy looking black suede mary janes. Note: I was never a socialy adjusted kid who fit in. So when I saw the other kids in their jeans and sneakers I felt more alienated than ever. Now, naturaly, I would rather go to a wedding in gym clothes (that I don’t normaly wear outside my home) – I’d totaly feel like a rebel doing that, than overdress for anything, feel like an idiot and look like an attention grabber who tries too hard.

  • Charlotte Fassler

    I had the exact same experience at a Bat Mitzvah except I felt like I wanted to crawl into a shell and hibernate forever because I was underdressed for a much more formal affair than intended. It was the end of the Mitzvah circuit and kids got progressively more casual, so I thought some dark jeans and a beaded fancy top with some sparkly flats would do the trick. WRONG. I was the only female in pants and the only person in JEANS.
    From that party on I found myself insanely overdressed for years to come. It never comes off as rude to be overdressed, I found people interpreted my fanciful outfits as respectful and I was more often than not complimented.
    Then something shifted, and now i think there is a confidence which comes with underdressing that I find myself practicing more frequently. I feel less confident when I am overdressed and try harder, like there is an insecurity in the fact that I tried.

  • kristina

    overdressed, always.

  • super_pile

    imagine that you life is exactly the way you want it to be and dress for it! thats what i do so i am often overdressed. but you know what? its great in life that the same way you can smile when youre happy, you will be happy when you smile. this works with your outfit too :-).

  • not John

    If I had to choose between the two, then maybe overdressed seems better, because then you are in a situation where you are the most fabulous person in the room, but I think one should consider the event or place and circle the outfit around it.

  • StephC

    This is tricky – as an east coast transplant to Northern California, I am frequently irritated at the Teva sandal/cargo shorts that are worn to church, dressy functions, etc. Still, I can’t help but think how liberating it is to live somewhere that focuses on who the person is (and not how they are dressed). I personally think denim with great shoes/jackets/accessories can work for most occasions, but maybe I have lived on the left coast too long now…

  • I have the exact same reaction to a Bar Mitzvah at which me and my outfit were horribly out of place. It was an outdoor backyard party and the rumor was that every girl was going to be wearing Solow pants. My mom (rightly so) forbade me from buying Solows, and I felt uncomfortable in them because I didn’t graspy the concept of a thong at the time. I saved up my babysitting money and bought a Solow skirt (I really couldn’t handle the pants). I was really excited that I had managed to mix my wish for fitting in with something kind of funky, but when I got to the party every body was wearing JEANS and a halter top. I couldn’t dance because my Solow skirt was too fidgety, and I never wore it again.

  • Hannah C.

    I’d say it’s better to be over than underdressed (that has nothing to do with the fact that I was recently talked to at work for being “too casual”). While underdressing may get you some cool points, overdressing is far safer in that you’re less likely to get yelled at by your aunt or your boss.

  • Lindsey R.

    Overdressed, always. But overdressed doesn’t necessarily mean uncomfortable.

  • hurhurhur

    I’m very comfortable undressing. Wouldn’t know what it feels like to be overdressed.

  • Nicole

    Mix it up! Today I’m wearing pink gumboots and overalls, tomorrow I might wear a sequinned lace dress. I say wear whatever takes your fancy and don’t worry about what others think.

  • Sabrina Haskinson

    I cant speak for anyone else, but I’m admittedly over- dressed every day of the week. It’s just a personality type I think.

  • Ghazal

    Underdressed! for sure. It just feels cooler for me. But when i’m overdressed i feel uncomfortable. as if i’m trying too hard. (big weddings are a different story. i’d never be in jeans for those.)

  • I have to agree with Hepburn on this one; I believe in overdressing.

    Irrelevant to this post, but relevant to the title… I thought this was going to be about overthinking dressing casually (which I’m completely guilty of). While it may seem easy to dress à la Birkin and throw on a t-shirt and jeans, it always seems to take several tries of different tees with different pairs of denim to get a perfect basic look. Ya know what I’m sayin’?

    • Meredith

      I had the same exact thought! I’m notorious for taking a laughable amount of time to nail the proper “effortless” look. Regardless of whether I’m overdressed or underdressed, I’m always striving for effortless. Which is clearly funny because, well, it’s not effortless at all.

  • DNA (designers+artists)

    I always say be overdressed, gives people something to talk about. 🙂


  • Desperate Hong Kong Housewife

    This completely resonates with me as yet again I’ve returned from a weekend break where every woman but me seems to have gotten the dress memo. Why is it that when I choose to wear a little dress to dinner when I’m on holiday, every other female in the restaurant is in white jeans and a peasant top? But when I choose the white jeans etc they’re all in cute dresses? Does this happen to anyone else? http://www.lastordersatthedoublehappinesscafe.com

  • Naddy

    In the society I’m living in, whenever I dress nicely for the day (simple dress, cute heels, etc) I get weird looks and get asked questions like “you look pretty today, are you going some where?” While when I wear the regular jeans, shirt, sneakers/flats, I blend in with the crowd.
    I think it’s a matter of wanting to stand out, and being yourself in the clothing you’re most comfortable in than blending in with the boring crowd.

  • I like to be both 🙂
    Mlle C.

  • Underdressed! Its better to be underdressed for sure. The trick is to do it from the heart and not because it’s a “trend” or “in fashion” at the moment 🙂 Underdressed fashion should not be “over-thought”
    Great post!
    And BTW: I think the outfit you wore to the wedding sounds lovely 😉

  • Ana

    Hey guys! Is it just me or the search bar does not work? Every time I go to click on it, it refreshes to the Man Repeller home page.

    • Leandra Medine

      Hey Ana. Working on it!

  • Jessica Jesse

    It is all about style and caring. Knowing what to wear, and when is an art. People look like fools either way underdressed or overdressed. When you take the time to look special and make an effort, it shows that you are aware of your surroundings and of the situation…and this is nothing more than mindful glamour.

  • CDJ

    As a former 17 year catholic school girl (exhausting), let me tell you there is no bigger embarrassment than when every kid at recess is wearing their casual clothes and you’re in your uniform because you forgot it was dress down day. 7 years out of high school, though, and I really miss that uni…if only it still fit…

  • I had a similar moment at an 8th grade birthday party and wanted desperately to go home. Now, after moving to the Midwest from the East Coast, I find myself perpetually overdressed because the norm here is so casual. (Think jeans at a “black tie optional”.) But I’ve accepted that I’m not about to leave, especially if I’ve made a dress for an event! You just have to own what you’ve decided to wear.


  • Alex Poirier

    My girlfriend and I live in a very rural area, where overdressing is almost frowned upon. We go to get-togethers with friends and are often questioned why we are so dressed up (when I say dressed up, I don’t mean a suit, or a gown…just not jeans and a tee).

    We’ve gotten used to the usual questions, and I think most of them know what to expect from us now, some have even admitted to trying to dress nicer if they know we are coming, haha.

  • Arianna

    It’s funny it’s a cultural thing. In Italy it’s quite the opposite, with my mum scolding me since I was little for wearing clothes which somehow were always “too casual”. Then when I went to college i realized a) everyone wore hoodies and b) they wouldn’t even notice if i dressed up. So first i felt discouraged to dress up and started wearing flats, more jeans than dresses etc. Until I finally realized that – what the heck – I should dress for myself. Overdressing for me is respecting myself, my sense of aesthetics, the place where I am, and that’s all that counts 🙂

  • Hereshoping Themayanswereright

    I think it’s fine either way depending on the person. I’m more comfortable being overdressed, but also found myself in a situation where due to time and geographical constraints I had to attend an extremely elegant, huge black tie event in DC, in casual palazzos and a little party top. Everyone else looked amazing and I stood out like a sore thumb, resulting in some whispers and condescending dirty looks.Fortunately I’m used to not letting people make me uncomfortable, and went on to have a completely awesome time. FYI women tend to judge you much more for inappropriate dress, the guys do not care and even seem to appreciate it.

  • Underdressing is becoming such a trend nowadays since minimalism is so chic. Check out some laid back looks at http://www.lezu.com

  • Devin

    I absolutely love this post, my favorite one thus far in fact. I have a very strong opinion that you can never be too overdressed (there are very few exceptions such as, you know, a fancy-shmancy prom dress at church or tuxedo at a picnic sort of thing). Thus I believe in the opposite, you can often be underdressed. BUT, if you are in either category own what you wear. Walk the walk. Confidence in what you wear shows, while here at college, there will be days I dress a bit more casual-thrown-together-but-put-together looks, and many days I dress up. (I love dressing up). Whatever day I choose I walk the walk. Be proud in your own artistic invention. You are the only unique person dressed how you are that day in the world. Own it.

  • Oscar Wilde

    “You can never be overdressed or overeducated.”

  • Arianna

    Underdressed or Overdressed it’s you being comfortable with yourself and how you look. That’s all the difference. http://www.littlemissarianna.blogspot.fi

  • Astrid

    I think it depends on what you define as casual.. I love the girl who is in black jeans, sharp blazer and on point accessories when everybody else is in a fancy dress because it feels so French to me, but you can’t push it too much. I would hate making the host feel like their event wasn’t important enough to dress for. I’d say, just make your outfit look like it was considered. But overdressing is a no-no for me on any occasion.

  • ashley kilback

    Over the evolution of my fashion career, I’ve developed the role of “the overdresser”. I’m usually always the one showing up in something that’s not on the outfit memo which turns into me receiving awkward eye-gawks, but I’ve learned to embrace it and purposely dress against the memo for the hell of it.

  • Maria

    Always better to be underdressed… Less is more and also cool is more… Leandra, You were even ” underdressed” at your own wedding with that leather jacket… So i must conclude, Cool is more!. Being overdressed is never chic!

  • Pahtrisha

    The trick is to be able to carry it off so it doesn’t matter whether you are overdressed or underdressed. At a wedding the rule of thumb is to not look like the bride, but other than that. 🙂 Love the way you describe your style and you should have no cognitive dissonance about looking great.

  • Pualani@TheRustedKey

    There are times when every girl feels the need to get overdressed and underdressed, which are all dependent on how you feel at the time and is indefinite.

  • Danielle Nordahl

    In middle school and high school I used to overdress, I think mainly as a result of everyone else being in a hoodie and jeans. I loved fashion, so this is how I stood out. Later, in college when everyone went out in a tight, short dress, tons of jewelry, and high heels, I felt like I was more myself, more comfortable, and had more fun when I was dressed down. When you’re afraid of falling or constantly pulling at your dress, you’re not really exuding confidence. So, I like the juxtaposition, dressing up for work, dressing down for a night out on the town when every girl is going to be trying so hard that you’ll stand out for not? But, that being said, I would never to do it if it would be disrespectful, like a dress code for a wedding or event. Though I don’t think Leandra’s outfit for the wedding was disrespectful, just a masculine, parred down take on black tie. More than anything, as most of you have already said, it’s how you carry yourself, no one will bat an eye, unless in admiration, if you carry yourself well and are confident and comfortable in what you are wearing.

  • Lainie

    I once admitted to a friend that I preferred to be under-dressed and she said, but you know it’s supposed to be the opposite right? I know that the ideal is that if you’re over-dressed at least you don’t look like the idiot in jeans, but I agree with you – I feel so uncomfortable being fancier than others.


  • Eve

    I’m afraid that, when it comes to frocking up, I fall into the first category. I’m an overthinker, I overthink. I put on stylish clothes and knock-off-but-still-very-nice-looking sunglasses, and feel pretty good about myself, up until the point I realize I’ve been lied to by my own shame-faced skinny mirror, and all that thought-through perfect getup would look 100 times better on a skinnier-looking, taller person. But by the time I’m done with my Carbonara, I think I must have dreamed it all.

  • Nora

    It might be so cliché of me to say, but I honestly believe that you should simply dress in whatever makes you feel most comfortable. One of the friends I mostly hang out with is fabulous in everything she does. She can be in PJs and make me feel bad when I’m all dressed up. It’s insane and unthinkable. Naturally, I would start overthinking way too much about what I was about to where when we met up.. and eventually look (and feel) even more ridiculous. That’s when I realized that I should stick with my simple, minimalistic style. It’s what I know and what I do best.

    That being said, I believe it was Mister Oscar Wilde who said that you can never be overdressed or overeducated, a statement I’d love to be able to live by.

  • www.sophiesstylenyc.com

    I prefer to be overdressed than underdressed.

  • Amelie

    This is the best post I’ve seen today!

    The Neon Guava


  • Gennea

    As a girl with a very hour-glass figure, I always over-dress because I feel like only thin people can pull off the under-dressed look. It looks so good on my skinny friends but when I or one of my fellow curvy friends attempts under-dressing it just looks drab and frumpy. With years of experience, I have learned one valuable lesson; if one is over dressed, hour-glass, AND sexy – then one looks like a call girl – and that is to be avoided at all costs. When over-dressing, don’t do sexy. Sexy is for under-dressing.