Finding Style in Trial and Error

You can’t get it right if you don’t first get it wrong. Check out Leandra’s path to figuring out personal style here.


It’s been said that if you fall off your bicycle, you should get back on and just keep riding. I understand that the larger metaphor-for-life was initially instituted to depress the plague of discouragement, but I also understand that the euphemism has prevailed because as humans, we have historically demonstrated that we learn from our blunders. Steve Jobs was pushed out of his own company in 1985 only to return in ’96 and eventually render every other business in the history of work obsolete.

Naomi Campbell famously fell to her ankles (no, really) while walking in a Vivienne Westwood show in 1993 but that’s frequently overlooked. And I failed my road test four times before I became a professional race car driver.

But when considering style, why does it always seem like if you’re not consistently “getting it right,” you don’t have it. There’s a saying that goes, “style can’t be taught,” which has been underscored by a comment Anna Wintour once made — “either you have it or you don’t.”

If this is true, it means that the ability to style is an inherent quality that a man or woman possesses. And if that quality is inherent, the supposition is that like with blinking, or with breathing, there’s no learning — from blunders or otherwise — to take place. Frankly, though, who’s to say that if you are one of these ostensibly lucky gene carriers, you can’t come into a few snafus along the way? Especially, I might add, in this golden era of pics-or-I-never-wore-it.

I guess it always boils back down to Instagram.

Last month I watched hundreds of comments rake in regarding a photo I posted of an outfit which included a blue bralette-style crop top and high waist burgundy satin shorts. The responses were mostly respectful but almost universally against the look. I called it the Obamacare of Selfies, primarily because most people hated it (and I understood why), but because I created it, I stood really firmly behind it.

The following day, I posted another photo (a full green look), which received glowing reviews — some even from the commenters who just the previous day told me I had “zero sense of style.”

It occurred to me then that to say style is inherent is fair but it is also vaguely flawed. This is chiefly because personal style is deep-rooted in opinion. Not everyone is going to agree but this is precisely what makes it personal (and often too, compelling). Is it a coincidence that the second photo was the one that received the positive feedback? Maybe, but it might also be a nod to my testing the trial and error formula and understanding what could have worked and what didn’t.

Much like writing, style is a muscle that needs to be trained in order to function as the best version of itself. Sometimes it works better than you knew it was capable of performing while other times it feels kind of weak. As a result, it can often let you down but there is an ultimate, baseline understanding that it’s always there and that it’s yours. Sure, it constantly needs to be challenged in order to continue operating successfully but what doesn’t?

Don’t wait for the bike to tip over. Throw yourself off that shit and see what happens.

Oh! By the way! I’m not really a professional race car driver. I do have my license, though.

Like Leandra’s style? See her denim challenge here. You can also check out her’s and the rest of Team MR’s Resort ’16 picks here. Watch her in The Chatroom with Linda Rodin talking all things beauty and style. You could also watch how she uses her pinky to do her hair.

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  • kirbybee

    I could not agree more with the notion that style – personal or otherwise – is deeply rooted in opinion. And furthermore, that that opinion is intrinsically attached to the idea we have of ourselves. When I judge the sartorial choices of another, am I not doing so under the veil of my own idea of who I am?
    That said, I do love the idea of style being trial and error. If making mistakes and falling into wrong-town are not only ok but expected, experimentation suddenly seems not just an option but the only option.
    Excuse me while I go outside and deliberately fall off my bike, if only to give the distressing on my denim some semblance of truth.

  • Liz

    What is so polarizing about the first outfit?

    • Laura Robinson

      I agree. I wish I could pull that look off. But, I am no waif and I’d probably look obscene or get picked up for solicitation.

  • bindi

    Totally agreed. While style cannot be “taught,” I think that it certainly can be learned; people can teach themselves how to cultivate a good sense of style–with more exposure and with more experience with what feels most comfortable and authentic. Our capacity to style can evolve just like anything else.

  • Great essay, Leandra!

    I actually really loved the first look. Both are great, but I feel a special connection with that top with those shorts.

  • I dressed like Eminem’s girlfriend (I still wish) from ages 14-18. I got to college and realized over sized sweatshirts paired with ultra low rise pocketless denim and dog hoop earrings wasn’t the classiest look. I think style can definitely be learned, I mean I learn something new on here every day about how to style myself. But there’s nothin’ like throwing a hood rat into a lilly pulitzer (ew) soaked campus! That was also the year I stopped wearing sweatpants with words across the bum. I like both of those looks, Leandra. You were on vacation, calm down peoplez.

  • You are absolutely right about learning being the key. To style and many other things. I also agree you should get enough opportunity to do it, even if/because we get to see the intermediate results. 🙂

    Speaking generally I still find it hard to accept people don’t know how to treat learning people in an appropriate way … As if being able to present perfect or at least likeable results all the time was the most important thing we are all supposed to do. I mean: shops need to charm our asses off so that we buy stuff from them, but a person is not (only) a provider of entertainment, desire, dreams … whatever. A person (be it private or professional) is always also a process and as such most interesting!
    And: while envy seems to be generally acceptable and might be considered a measure of your success, the thinking/reacting mechanism “I envy this person her success (general state of mind) and today she did something I dislike (special occurrence seen subjectively), so she obviously totally lacks style (general personal characteristic)” is plain stupid, even as far as insults born of envy go.

    (I used to draw dresses for my friends to have them sewn for the prom and they appreciated me for that. I also used to clean my granny’s pigpen on Saturdays – so did that make me a fashion maker or a damn farmer girl?!? 🙂 Both?)

  • I don’t think it is fair to compare the two photos/outfits by the way they are displayed. The first seems as though your just hanging out at home while the second has a more staged aura (it’s the backgrounds). Maybe if the first outfit was recorded outside in a park , at a festival, or an outdoor cafe it would be more “accepted” by your commenters.

    Also, I went to a fine arts college and having style meant following a check list of items depending on the sub category of “art kid” one followed. I don’t think that’s far from how many people perceive style in general, but this seems to leave out the personal.

  • So disappointed you’re not a professional race car driver Leandra!

    Mafalda ❤

  • Elizabeth

    This is particularly timely because a) I ACTUALLY fell off a Citi bike the other day and when I say “fell,” I mean that I was hurled like a boomerang towards the concrete next to a group of brunchers trying to have their mimosas in peace and b) this weird spring, but not spring, thing happening right now makes experimenting with style that much scarier and more challenging, but ultimately more rewarding. In case anyone was wondering, there are nice people in New York who provided me with a bandaid, some water and few words of encouragement. Just like that, I was back on the bike.

  • I love this Leandra! This is why Man Repeller has a special place in my heart – you encourage readers to take risks and not worry so much about what others think. It’s always inspiring to hear how you deal with your naysayers. While I like to think a certain love or passion for style can lead to an innate fashion sense, I agree that, like most things, with practice we can get better and feel more comfortable with those risks. In the end it’s all about loving what we’re wearing and owning it. So as usual, you’re awesome:)

  • Style is totally opinion-based, totally personal, and totally trial and error.

    Your personal style is like yoga — if you don’t fall down *at least* once in every class, you’re not learning or growing.

    Also :: fuck the haters. They are entitled to their opinion, of course, buuuuut — I can not like your style and STILL be impressed that you’re expressing it. Because doing THAT is scary, and brave. Anyone who comes down hard for you being different? Their opinion does not count.

  • amommy

    You have such a beautiful smile 🙂

    • Leandra Medine


  • Amazing. Having a bad outfit makes us appreciate a good outfit even more..

  • Guest

    oh man, I loved that first outfit so much!! Made me wish i was smaller on top so i could fit into a shirt like that…

  • always a pleasure to read your wise words Leandra. xx

  • Laura Robinson

    I keep a file of photos of things I like in my iPhone. I look at them over and over and decide what it is I like about the piece/outfit. Sometimes it’s just the color of a piece in a style that wouldn’t flatter my body or go with my lifestyle (I’m a middle aged, pre-service teacher that lives with two dogs, two cats, two goats and three chickens) but then I can look for or make (maybe) something that has whatever the feature I like is in something that does flatter my body and fit my life.

    • Leandra Medine

      Oh. I really like this. I am everlastingly fascinating by why we like what we do (as in, is it because it reminds me of other stuff we already own? Is it completely different? Is that it’s own form of escapism?)

  • Cristina Feather

    When I was a kid, my mom used to dress horribly on a day to day basis. But, from time to time, for a special occasion, she would pull off this amazing outfit that blow my mind away. As a child I was obsessed to look like the cool kids and I blew it every single time. As I mentioned, I had no role model. Even now, after so many years, I constantly blow it – but everything is so different now. I like taking style chances, I like to experiment no matter what others will think. Now, I am happy to say that I don’t give a damn anymore about what others say.
    Your article makes me happy – because I truly believe that style can be taught. How would you explain Kelly Osbourne or God knows how many others… (should I risk and say Kim Kardashian?)
    It’s definitely easier to be born beautiful or graceful, but that doesn’t mean that we, the other 99,8% of the world, don’t have a chance to obtain great style.
    Thank you for always being an inspiration in that direction 🙂

    • Laura Robinson

      The thing I love about this comparison is that she’s stayed true to herself and is just pulling it off with much more elegance. I suspect she had some help from a stylist, but still.

  • Greer

    I like the crop top one much more what is wrong with people!

  • Gré Tee

    both outfits are awesome! because they suit you!!!!

  • I think I have found my ‘style’. Wrinkly blouse. I’m sorry but I just can’t for the life of me perfected the art of ironing. That’s magic. And I didn’t go to Hogwarts.

  • I’m a firm believer in the concept of “owning” your look. Whatever look that may be, if you wear it with confidence and believe in it, that could make the difference between a look that was a success or a failure. Ultimately, it’s the wearer who makes this determination. I’m not saying I can always pull this off, but I believe most people are unaware of what they project to others. I also believe that this confidence comes from experience (hence the hypothesis that you can learn from your fashion mistakes). I am a classically trained chef. When I first moved to Paris, I had no confidence as to my prowess in the kitchen. I knew I was a good cook, but it took years before I could improvise and “create” without fear. I can sum up the cooking analogy in this way: You have to know and understand what makes a dish good before you can figure out what is bad. You have to train your palette. If you have never in your life tasted a hollandaise, how can you determine if the one you just made is good? Fashion involves far more subjectivity (there’s not a lot of personal opinion to take into account when something tastes like crap) but experimenting still comes with confidence and learning from mistakes.

  • MargaretInArabia

    I actually loved the shorts. How cute for South Beach or Cannes or Times Square or wherever when it really warms up. If most readers didn’t like it, oh well. Most readers couldn’t pull it off anyway.
    Style is inborn, an attitude that extends to all areas of life. In this case we are discussing clothing choice.

  • Dancingcheektocheek


  • dreamy show
  • BoyfriendsandBlazers

    Succeeding in constant style has become almost equally as important
    as succeeding in the “real world.” What the outside world can
    gather based off of what we put out is so significant to us that sometimes we
    misrepresent our own selves for the sole acceptance of society and what is “cool”.
    I think that the problem here lies within the fact that we realize it is not up
    to society to create us or accept us, it is up to us to show society how we
    were created, and how we all differ, and that the real beauty lies behind that “differ”,
    which is what inevitably makes us individuals.

  • Karma

    I completely agree; I actually love the first outfit. Style is something unique to everyone – something one person likes, another hates. This is why I believe you should wear what you love, because confidence always goes with everything.

  • Mackenzie Chambers

    Love your posts and at the risk of self-promoting- there is much that changes about an outfit when your body is open and comfortable with its bones. This takes more than muscle building or soul cycle; it is as much dependent on what stretches or opens.
    I think your first look would transform if your shoulders and upper chest were opened up; it would lengthen your torso so the bow would not look as though it were pulling you down.
    I would love to offer you a gratis session in my DUMBO Pilates studio to show you what I mean.
    Let me know if you are interested. I’m not posting my website so you know thi is not about advertising!