YOLO Dressing

For those days when it looks like you got dressed with a little liquid confidence.


Life for the YOLO dressers must be so much fun. There are plenty of them in New York, those brave individuals who look like they opened their closets and just went for it, you know? A flower-embellished headband. A full red leather look donned mid-day. Where my go-to fabric is denim, theirs is like, velvet, and 9 times out of 10, they’re in heels. They wear outfits in the true definition of word, as if each styling choice is purposeful, necessary, eager. It’s the opposite of effortless. They truly get dressed.

I walk past two YOLO dressers on my way to work every morning. Let’s call it 9:00 by the time our paths cross if I’m running on time and choose the park-route. Picture me in my uniform of white jeans and a sweater, footwear dependent on weather. Now picture them, on the other hand, a boy and a girl, looking as if they’ve raided the closet of Lady Gaga and then swapped clothes with Boy George. They’re in full looks, the both of them: sunglasses covering their faces, wild hats, side-laced pants. It’s not my style at all. In fact at 9:00 AM I’m not sure I even have a style, which is why I’m so enamored with theirs.

For many YOLO Dressers, a snooze-worthy Wednesday is as good a time as any to get done up to the much-forgotten-nines. Weather isn’t an excuse. Cramp-pants aren’t an option. They treat the streets as a daily runway and their world is a fashion editorial — I’m just living in it. While talking to Leandra about my fascination with their daily sartorial balls-to-the-walls-ness, we pin-pointed another type of YOLO Dressing: that which tends to come in the wake of specific occasions, which inspired a bit of imaginary YOLO window-shopping…

For, say, a breakup:

Or perhaps to celebrate a raise:

For a milestone-of-a-birthday party:

For the sake of nothing more than an erratic, vacation-bound shopping spree :

And if I were to ever join forces with that that rare city breed who look as though they’ve gotten dressed in the dark, bolstered by  bachelorette happy hour and a bottle of liquid confidence yet, still look strangely fabulous?

You know what they say: Carpe Diem, it’s Latin for YOLO.

And you know what we say? You Only Live Once.

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  • maud.schellekens

    Love this article!

    XOXO Maud


  • Jackie @ Kleiden drew

    Find that inner 3 year-old and go for it! (TRUTH: I’m a hypocrite. I wish I had the noive to do it in spite of what I think about my size…but for now will live vicariously through Anna Dello Russo and Iris Apfel.)

  • YOLO dressing is a fantasy which I want to make a reality! There are days I just feel like busting open my closet doors and going for it! I should and am inspired by this post!




  • Quinn Halman

    What a coincidence because I have a casual day today! If you asked anyone at my school they’d say I YOLO dress but it just comes down to the fact that I am confident in my style. So take my Rick Owens drop-crotch pants, isabel sneakers, adidas flower jacket, or leave it!

  • Katie Weber

    There is a (large) part of my brain that is a YOLO dresser. You know, the part that says “It’s Monday, why wouldn’t you wear 5 inch heels covered in glitter to the office?” The part of me that understands what is and is not appropriate (or, at least understands it during the work week) steps in an keeps us all on track.
    Needless to say I regret not adding a bit more YOLO to my outfit almost every day

    • Amelia Diamond

      Wearing the 5 inch heels covered in glitter to the office will make Monday a little more fun! Even more fun is the fact that glitter will be stuck on you for the remainder of the week! Glitter rules.

  • I live in a world where people wear haute couture to buy bread and milk — it’s an illusion that sustains me through mundane mondays, so Oh Hail YOLO dressing! http://www.madelienerose.com

  • Thanks for this discovery, I had never heard of YOLO dressers!

    Mafalda ❤

  • monkeyshines
  • Parrot the parrot

    It’s truly inspiring see eccentricity and joie de vivre represented on this blog. But I have to admit something about this post made me queasy. I think the twist in my gut, stems from the POV of the writer (and sense of implied of alliance with the readership ie me) which reminded me uncomfortably of a popular girl in high school commenting on the arty creative kids “Gosh, wow, they’re so WEIRD it’s kind of great and HILARIOUS — I mean, (ha ha) in an UGLY strange way they’re actually kind of cute though OH MY GOD I myself would die if I ever wore those crazy clothes.” It felt, I guess I’m saying like a backhanded compliment. I wonder if instead of wearing J. Crew or whatever popular girls wore in high school now the popular girl wears — well, she probably still wears J. Crew — but she wants people to think she’s wearing Celine. Look, I don’t mean to be a jerk. Personally, I’m not immune to the vibe of the zeitgeist and how minimalism and basics and anonymity feel chic now — but I guess honestly, I feel anxious that the tenor of this blog might lose Leandra’s originality. To me being a manrepeller chick meant being ONE OF the arty creative kids who don’t give a shit about fitting in, who dress to express THEMSELVES, not a snide smug passerby in jeans and a sweater who looks at fashion as a uniform to acquire and regards those with flair as amusing alien entertainment. Screw conformity. To hell with obsessing about what’s chic all the fucking time. Let’s express ourselves. Let’s repel not just men but women! Let’s repel everybody! Let’s — and this is cosmic my friends — even repel ourselves. Vive la repulsion!

    • Amelia Diamond

      Hmm… first of all, thanks for your comment. Superiority over anyone was not this article’s intention. Actually first and foremost, it was supposed to be a total celebration of “you do your original you.”

      The mention of me in my jeans and sweater was supposed to be making fun of myself. I dress pretty boring (and LAZY) which is why I’m so fascinated with the people who really get up and get dressed and make an outfit each day. My biggest joke is, “I work in fashion…can’t you tell?” while gesturing to my “outfit” that is not actually a cool outfit at all.

      For sure, I don’t always “get” these crazy dressers — but I’m not making fun of them. Anna Dello Russo, for example, she’s a total YOLO dresser. She has balls, and I respect that. This is why I love fashion so much, because I can be an observer, and a total fan, even if I don’t choose to participate in my daily wardrobe.

      And further to your point, you’re right, Man Repeller is about originality. Which is why I’m trying to celebrate that, to point out that though a red velvet jumpsuit isn’t my style, I love that someone was brave enough to go for. (And on any old Monday, for example) The underlying credo of MR is you do you — whether that’s wearing a bird on your head, OR if it’s wearing a boring old sweater. We try to promote confidence, and I’m sorry if that wasn’t your takeaway with this post. Ultimately, it was a supposed to be a reminder that it’s fun to have a little bit of fun with fashion (especially in these days of…dare I say it…#normcore…)

      • I have repelled myself

        You know what? I’m sorry, Amelia…! At the risk of being inappropriately earnest, I think my gut reaction to your piece probably had less to do with you and more to do with me. I never comment on anything online and now I can see why — it’s so easy to be hostile (or come off as hostile), so easy to spew like nasty spewers out there. Especially when you’re anonymous — maybe there’s something about being anonymous that is dangerous. And… aha… therein lies the rub! I think what was making me feel queasy was my own anxiety about my own lack of originality in dressing. I’m wary of blathering on and on but maybe there’s something relevant or relatable in the dilemma I’m feeling. If you’re not going to be an ADR/ Daphne Guiness type — if the best way of expressing YOURSELF (uh, myself) at this moment in time is in a simple way — if what feels right to you (uh, me) is wearing a white t shirt and white sneakers and wide legged pants — how do you not end up just being one of the herd? Basically how do you dress in an original way if what feels right to you is what feels right to so many people? Maybe as an instinctual dresser who has always taken a bit of pride in having a sensitivity to what feels RIGHT and NOW, I’m confused how to deal with the speed at which trends are proliferated virally. It used to be that I’d feel an instinct to wear something — stan smith sneakers say — and I could happily do my own thing for at least six months before it became a trend (not that everything always did or anything — I mean, nobody followed when I was vibing on spats … haha)…. But now the trend setters are followed so quickly by the trend followers that it’s unnerving. It’s like lightening and then thunder — when they’re too close together you’re going to get burnt!! And I’m particularly confused how to handle my desire for basics when I’m surrounded by others in basics — and anxious that it is a sign of my deteriorating creativity. A deterioration which I then transferred onto the manrepeller blog. At least that’s what my shrink might say, that is if she was dressing norm core instead of being someone who is totally uninterested in fashion. Anyway, my bad. Carry on with your repellent self!

        • I agree

          I agree. Something about this post irked me too. Maybe it was this phrase — i: that rare city breed who look as though they’ve gotten dressed in the dark, bolstered by bachelorette happy hour and a bottle of liquid confidence … t is ultimately concluded in a complimentary way but is a bit harsh.

        • Amelia Diamond

          No “my bad” needed! These types of discussions are great and necessary, they get the juices flowing. You wrote, “Basically how do you dress in an original way if what feels right to you is what feels right to so many people?” This is the hardest thing! And my only answer: attitude! But it sounds like you have the right one. I meant it when I said “thanks for your comment” and I hope you continue to do so on MR. Always jump into the conversation, or feel free to start one.

    • LilyP

      i couldn’t agree with you more, i dressed like this in HS too, and I always had to deal with “comments”, like, from other kids “‘you need Prozac, and color coordination’, or, ‘are you schizo’?” AND I WENT TO AN ARTS HIGH SCHOOL. pretty much reached into my closet and wore whatever I was feeling that day, even if it was a red polyester top from the 70s and a giant rayon broomstick skirt printed with seaweed…its so funny now this is being celebrated, we non-conformists – bullied, ridiculed, or just plain misunderstood, bravely paved the way back in the day for all you fashionisitas.

    • Platsy

      Amelia doesn’t have to have good style to be interested in style. Plenty of fashion people aren’t fashionable themselves — like the Rodarte sisters.

  • Charlotte Alice Taylor

    I love this article! People who dress how they want always brighten my day, if everyone dressed with total confidence the world would be so much more interesting!


    • shp.

      BUt isn’t this whole BLog supposed to be about people who dress the way they want — . Is the anxiety that hte blog sold out. Maybe Amelia is just more conservative and not so into being creative as Leandra is. but being concertvive is okay too. It just means she s more insecure.

  • So much fun indeed! I love the pictures and this article: very inspiring!


  • What would a YOLO dresser forced to take Benadryl at 7:45 AM on a Monday wear?

  • I’m such a fan of this. I think you can have fun and do really bold prints and colors but keep in mind the atmosphere you are going to be in and make sure it is appropriate.


  • This post is awesome. My birthday is coming up and you’re making me think that I can justify an impractical, splurgy piece for this occasion. Even though I’m in the boring, easy dressing category 9.99 days out of 10.


  • Hmmm, is it bad I find the majority of these items incredibly appealing?

    • Amelia Diamond

      no way! i do too!

  • Mari

    I love ❤️❤️ this idea and i embody it to an extent but this has inspired me to truly embrace and go the whole hog!!! Im excited!!!

  • Jenni

    An always timely reminder that at its heart, fashion is about having FUN – feeling confident and wonderful about yourself, for yourself – there is such a buzz when you’re having a great hair day, have nailed your sartorial choices and feel like the world is your playground…great post & inspiring images X

  • Jess Molina

    Finally someone gets it. Thank you!

  • Kyla

    I love Amelia as a writer. More importantly I LOVE how often she responds to comments and in such detail! It actually is really lovely and brings a really personal feel to the blog, which is why blogs are attractive in the first place. It is really appreciated Amelia!

    • Amelia Diamond

      Love you as a reader! Thanks Kyla.

  • ShopmeRoma

    circus time?… hadn’t seen any of them in town…

  • Agnes

    I love you!!!

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