What Happens When Getting Dressed is No Longer Fun?

I’m having some trouble getting dressed lately. This must sound like a fairly benign disclosure, particularly for someone who has essentially made a career of speaking publicly about the extremely private. But this particular bout of difficulty is ripping the rug out from under me because I’ve spent so many years believing that who I am is what I wear, making a case for style as a litmus test for identity. This practice goes beyond the personal — it’s the basis of a business and a brand. So what happens when it stops working?

I get out of bed and head towards my closet, excited to get dressed, but once there, I find myself paralyzed. It feels a lot like writer’s block — you have all the words and yet, you cannot compose even a single sentence.

Everyone experiences these spells of un-inspiration among their own stuff. You feel blah, you’re anxious, you’re busy — for whatever reason, you don’t want to think about getting dressed. So you rely on your closet tricks, the top-shelf, blah-proof garments that always work. Most of us have these tricks. For me, they’re high-waist jeans and striped tees, button-down shirts and denim cut-offs. I’ve even pulled out some newer ones, shin-length socks and tea-length dresses, but none of it works anymore. So what do I do? Can I do anything?

To try, I tracked how I dressed for a week to figure out if it would tell me anything my mind wasn’t yet computing. Here’s what the log looked like:


I feel foggy. My stomach is slightly bloated, my thighs are kind of hairy. My inclination is to wear something bright, because it seems pretty nice out, but I can’t bring myself to. So I rely on trick number one: a new linen shirt, which I basically rebuy every single Spring, and denim cut-offs that I have had for years. Add shin-length socks and suede loafers and I feel good enough to walk out the door.


Foggy again, but I don’t feel like dressing so plainly, so I’m gonna fight the fog. I can fight the fog! Today I’ll wear a gingham shirtdress that basically comes with matching pants. But now I’m relying on someone else’s vision. This isn’t a look I put together, it’s a look that was put together for me. Completely prescribed, but that no insurance will cover. For what it’s worth, I feel excellent.


It’s raining, but if I have to see another sweater, I’m giving up my passport and moving to the sun. I put on high-waist white jeans with a striped T-shirt and a Pepto-pink blazer. I hate how I look. The clothes are wearing me, I’m not wearing them.


This tiger top and zebra skirt are the first pieces to catch my eye today and that’s why I’m wearing them. Easy default. Feeling? Neutral.


One last ditch effort: a green folk skirt with a similarly colored tank top, plus satin sandals and a clutch. Again, I don’t feel much like myself, but it’s good.

Deduction: It seems I felt my best in looks that weren’t mine (see: Tuesday, Friday). This scares the shit out of me — am I trying to escape myself? What am I running away from? For each time that I rely on a trick and it works, there is almost always another time where I do the same and it doesn’t. This was true between Monday (when I felt okay) and Wednesday, when I wore the striped shirt and jeans. I spent the majority of that day wanting to go home to dream up a spectacle that would eradicate the paradoxical doldrums of a pink blazer.

The thing is, if I had gone home, nothing would have transpired. I’d have gone to my closet, looked around at clothes that I had deliberately selected to live in there and thought to myself: Who is this person? I think this is bigger than a lack of fashion stimulation; I’m outgrowing the identity I have carried through so much of my 20s. But it’s not just my identity because of what has been built — both personal and not — around it. If that sounds dramatic, it’s because it is. Not knowing how to dress has thrown me down an existential spiral that is forcing me to wake up to life. But it’s still so cloudy, so it’s probably best that I wait for even just a sliver of clarity — a pop of excitement, maybe a pair of shoes or a weird winged dress — anything that will display itself and remind me that even through the most radical change, you never cease to exist. I am who I am — we are who we are. I hope.

Photos by Edith Young

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  • Katie O’Brien

    The feeling I get right about now is an anxiety for a new season. Pre Fall is the answer to your dressing woes. Summer is such a hard season to dress for- I love layers, boots, and wearing head to toe black. I find this season the most challenging to dress well for. Pre Fall gives us that link between the past a new season. Open toed boots, lightweight jackets, new silk tops etc. Fingers crossed for a strong fall and pre Fall fashion season.

  • Hmmmm how do you feel when someone else styles you? Like the switch with Amelia. I wonder how you would dress after a week, or longer, of not dressing yourself.

    • Leandra Medine


      • Gene

        But if you could control that impulse, suffer through a week, think how motivated and revitalized you might feel about dressing yourself again! Or get your husband to dress you. Quasi serious, I just want to read the follow up article!

  • Alex S

    Leandra, I do have some good news for you: Malcom Gladwell just released a preview of Season Two of Revisionist History. I gather you’re as excited as I am based on your Monocycle Malcom Gladwell sign off (which makes me laugh every single time).

  • I’ve been wanting to burn my entire closet and was secretly hoping that would be the advice 😉 Nothing is inspiring to me anymore!

  • Blanche

    I read somewhere that around 27 years old, Jupiter comes back around to the place it was when you were born, which creates lots of disruptions. I’m a rational person (I think) who studies finance, but at times I fancy listening to the supposed messages the universe sends. 27/28/29 are supposed to be these real tough years (as Cobain and Hendrix and the rest of the 27 Club can attest to..). Sometimes I forget how young you are, based on the fact that you have an amazing business and are such a great writer. Give yourself time. Don’t get discouraged. Ultimately you will transition fully into the person you’re meant to be and things will finally make sense.

    In the meantime, I hope you know how loved you are, by many women like me, who admire your style (no matter how bland you might feel) and your overall badassery.

    • It’s Saturn! Saturn return.

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    • Suzan

      Yes seconding this, especially the last paragraph!
      Take good care of yourself, Leandra and just ride it out (ugh)! Sending much love and strength your way!

    • Lauren Holt

      I one hundred and 20 percent agree with said statements above. Also I firmly believe everything happens for a reason and that every happening brings you to something : a lesson, a new perspective, new found joy, new skin ( like a new side of you ) , etc. So yay for feeling blah about getting dressed ! It is bringing you to something new ! And I bet its a good thing 😉 🙂

    • Mariana

      I just celebrated 31yo and I think that that jupiter shit is taking too long lol

  • Loving Tuesday’s look HOT DAMN.

  • Michelle Blanco

    Is it just getting dressed that’s inducing the blahs? I wonder if it’s more than just the clothes that are hazing you out. I’ve had that hazy feeling and I’ve learned in therapy that is usually the result of an emotion be suppressed. Sometimes all it takes if for me to say to myself “I don’t want to be here” or “I really dislike this person’s behavior” or something to get the fog to lift. Sounds like a really interesting dilemma. Curious to see what you discover!

  • Gracie

    I feel like in spring and summer, I hate the idea of getting dressed because I didn’t make enough of an clothing identity for myself in the fall and winter, if that makes sense. Also, I wear high waisted jeans and striped tees basically every day.

  • Betty

    tues/fri looked best. the other days felt contrived..trying too hard. however, i’m at the point where I get the point of a uniform – or rather, there are a few silhouettes I’m always comfortable with and I change those up. slip dress+cardi; boyfriend jeans,chanel shoes, tank top, and some sort of cropped jacket – leather,denim, etc, oversized wide leg jeans w/ tight baby tee; skinny jeans with an oversized top (usually Pam&Gela ripped sweatshirt) and heels, and once in a while a really short mini with a sweatshirt or tee and chanel flats. even though my uniform is more than black pants/black turtleneck, i have a lot of options. can wear same silhouette 5 days a week or a different silhouette each day for 5 days depending on my mood. Limiting to these styles makes it much easier. What i really love is changing out the jewelry daily. Big bold pieces – clunky necklaces, huge cuff bracelets, multiple rings. Some days rows of chanel pearls. The jewelry is where I express most how I’m feeling each day. And yes, I’m known to over accessorize to lift my spirits.

  • Mia

    There’s a listlessness/ sad / blah look in your eyes that’s usually replaced with a more alive / crazy (in a good way) gaze — I think, perhaps, it’s not the totally the clothes- rather, the you inside which is struggling – manifesting itself in clothes.

    Is it an option to just stay home for two days in pajamas- till you FEEL like you MUST go out- and are excited … and then see what transpires?

    ALSO- perhaps some immersion into nature would help –

  • J

    I suggest a weekend camping trip upstate with friends, denim cutoffs, a swimming hole, and boxed wine by the fire. It helps with the blahs of all kinds.

  • Caitlin Crow

    this is so timely–same same same. nothing feels right, looks right, makes me feel like “myself”, plus it all makes me question what “myself” even is. compounding the issue is my purchasing timeout and trying to get extra creative with what i have (i mean, there are pieces in my closet i’ve still never worn out of the house, for crying out loud). alas, i still seem to hate everything i concoct. the subsequent sartorial dissatisfaction puts me in a foul mood with a side order of shame because i feel superficial that it bothers me so. please report back when you have discovered a way out. <3

    • flamesonthesideofmyface

      Can relate – and yes the shame too for having the privilege to care about these things! But I’m reaching a point in my life where I am finally resisting the patriarchal notion that any concern coded feminine is frivolous – “shallow women and their clothes”. Then there is the guilt about wasted money spent on things no longer worn, and the waste of the planet’s resources. It’s a lot of inner turmoil for something that should be as simple as covering one’s naked body so you can go out in public. But. There is something empowering about your closet reflecting who you are at this stage of your life. As a mom, lately I’ve been purging the unworn heels and going out clothes, and instead of being depressed, I feel like I’m embracing my choices more whole-heartedly. (Splurging on some great flats and sneaks helps too 🙂

  • Anne Dyer

    Oh that damn Saturn Return. It’s REAL. I was a hot mess at 28. And then I cried when I turned 30. I was so fucking happy. I felt like I was shedding the skin of my 20’s. Which were amazing but fuck they are messy.

    • Even though I officially do not believe in these things, I had my 28 too. It was great.

  • Dylene

    Wow talk about the right word at the right time. Really enjoyed this post. I’ve been feeling similar the last few weeks (I’m almost 37 so I don’t think it’s an age thing). I’ve been thinking maybe it’s because of all the enhanced bad news of world conditions. Anxiety and overthinking sometimes cloud my creative juices from flowing. Whatever it is for you I hope your outfit picking joy comes back to you ASAP! (Tho you would make a cute mannequin too… lol)

  • Ann P

    I would not go back and relive my 27 – 30 years for a blank check for life at net-a-porter. That stuff they say about it being a time of evolution and shedding what you don’t need? That sh*t is real. I think you might have just stared on the evolution bit Leandra, so buckle up lady! It’s a roller coaster. Hopefully being sartorially stuck for a bit is the worst of it for you.

    The good news is that it ends… and that you’ll be ok… and you’ll be pretty pleased with who you are at the end of it.

    Oh, and Blanche is right – your badassery and style are inspiring. I’m 45, was in a massive rut, but since I started reading MR over the year or so (ok, I’m late to the party) have rediscovered my who-gives-a fuq attitude to dressing, and that’s pretty much all on you lady. And now I’m off to [gasp] mix some prints and hopefully horrify selected people in my age group.

    • Ha ha ha… amen to that.

    • Late to the comments thread but wanna back up what Ann and Blanche said about your badassery and style being inspiring. Generally speaking I dress within the confines of what’s deemed societally acceptable, what some may call boring. (I haven’t always though! Where my high school self with her affinity for bright colors and excessive layers went I may never know.)

      BUT some days I’ll eye the pieces in my closet and put an outfit together that’s just a littttle bit different, a little out of the norm from what everyone else around me wears. That’s MR’s influence 150%. I’ve started wearing my hair naturally curly after years of over-styling the shit out of it, and that? That, too, is because of pieces I’ve read on MR and women I saw here being unapologetically themselves.

      I’m in my late 20s and am nowhere if not in the ever-present midst of an existential spiral. So I get it. I hope you find that sliver of sartorial clarity, but for now I just wanted to pop in and say that what you do on this slice of the internet makes a difference.

  • sleepingonsnow

    <3 <3 Whatever you feel is okay. Sending you love.

  • Allele

    We all have times when our work, or our image, inspires less then usual. You are in the lucky situation to be able to write a blog post about it without problems. It will get better!

  • Rachel

    I think you should try a haircut.

  • erin

    Have your mom dress you for a week. Your identity will reassert itself in force, and FAST ^_^

  • Slushee

    Yeah – I echo some others here. It’s about what is going on inside. Your mental energy and space is on other things right now, so forget about styling for a while. Or perhaps you need to hit re-set. I’m on a shopping sabbatical right now. I need to stop acquiring for a while so I can out what I’m lacking/ what I want.

  • Literally the only feeling I can muster up for any item of clothing/fashion in general these days is “meh.” Maybe it’s politics?

  • Paul Pham

    I think it’s your hair…maybe a new cut?

  • primadarling.com

    For an off week you looked pretty fab! I would never even dare to publish my off days but remember we all have them.

  • I felt this way when I was in Hong Kong a few weeks ago. It wasn’t what I expected, (particularly the shopping and style) and I started questioning my values and desires. There were so many designer stores, and an overarching amount of ornamentation, that the excess cheapened the experience and the fashion. I am still standing still while choices are swirling around me, and it’s so uncomfortable. This is my signal–change is coming. Ugh until it’s here!

  • Also, love the front page of your site today! It’s fun and chock-full, yet flows very nicely while maintaining congruity.

  • This speaks to me so much. I’m 22 and still have a lot of clothes from when I was 15. I’ve been having a style crisis recently too, trying to dress like an adult but sometimes I think I look like a kid trying to dress up like an adult… then I end up regressing to my usual leggings and t-shirt or sweater. But that’s OK. I’m learning to be more comfortable in my own skin and figure out what clothes I feel comfortable in now.

    If it helps, you still look super stylish in all these looks! xo

    • Karna

      Also 22 and the last couple of years I realized I don’t feel comfortable in the same clothes I wore as a teenager. So I’m slowly updating my wardropbe and discovering who I am and what I like to wear again. It’s hard when you don’t have that much to spend or even know what context you are meant to be in! Tried really hard for a while to build a basic wardrobe, but discovered I’d much rather dress to make myself happy. It’s important to remember that you don’t have to take style so seriously!

    • Adrianna

      Girl, I’m 28 and still wear clothes from when I was 15.

      I found that I dressed “more adult” ages 20-23 because I wanted to be taken more seriously. I’ve reverted back to t-shirts and skinny jeans.

  • Ecem

    Leandra! You look AMAZING. YOU single handedly are the reason i decided to introduce colour to my wardrobe which previously consisted of black cotton t-shirts and ripped jeans. YOU are the reason I have a mild obsession with the combination of anything velvet and animal print. You have been a massive influence on me both in terms of style and attitude. Thank you thank you thank you!

  • Georgie

    Hi Leandra,

  • Georgie

    Hi Leandra,
    First time ever commenting!
    I had been feeling much the same way as you recently, completely uninspired by my wardrobe and usual style. Last weekend, I went from having hair about the same length at yours to getting a lob just above my shoulders. It has honestly brought new life into how I see myself and my wardrobe doesn’t feel so redundant anymore. There’s my tip !

  • Lilly Bozzone

    I was in a major fashion shlump the past couple of months. too I wasn’t feeling good about myself on a lot of levels and it showed in how I dressed. But this brings me to another thought that your article resonated in me which is the bigger issue I’ve been trying to sort out in myself lately.

    As women who have built identities around the way we dress, expressing our internal with the exterior, what happens when we depend too much on the material to make up who we are? Where is the point in which our clothes end and we begin? What happens when we start depending on clothing to tell us who we are, and not the other way around?….

  • Kat

    It could be the change in seasons… winter always seems to hang on just that little bit too long and I get so fed up and impatient waiting to be able to wear bare legs and summer things.
    Try wearing your summer clothes but add leggings or a jacket to make them warm enough?
    Or just have a look at your wardrobe and think – what would make the biggest difference in here? I recently realised that while I have some dresses and a bunch of different skirts, all my tops are basically the same, so I bought a different style of top and it made a huge difference to my wardrobe!

  • Kay Nguyen

    Absolutely love Tuesday and Friday looks! Love your style so much <3


  • Mandy

    This is one of the most important things I’ve read this week! I also work in fashion and influence can be so damn deadly! Constant need to be authentic to yourself and then trying to tune out everyone else’s expectation of seeing your ‘daily looks’ Loved this article!

  • Mandy

    Also, I downloaded this APP called StyleBook where you are able to upload your closet and basically make at home polyvore boards of your own clothes. When I’m feeling blah I try to recreate outfit builds and the app also gives you logs of clothes you’ve worn the most, or clothes you’ve never utilized. It helps get through the slump

    • Adrianna

      This is part of living in NYC with limited storage, but I feel anxiety about not utilizing all my clothes. (I’ve already donated probably 1/3 or maybe even half of my clothing the past couple of years.)

  • Lil

    Tues is my fav!!! Leandra=modern day Carrie Bradshaw (minus the needyness), girl can rock anything!

  • Elissa K. Waybright

    Leandra, I’m so glad you wrote this article. I am clearly not famous, but also identify myself by how I dress. It is what got me out of bed in the morning or excited about an occasion (dramatic much? 😉), but for the past couple years I felt my interest slipping. Personal setbacks, weight gain, etc. all transpired, but I have really been trying to put a finger on what it is and it’s none of that. Because it’s not the obvious, I have no clue of where to start or what to draw inspiration from anymore. Please keep us abreast on your own journey and maybe that’ll snap me back into closet life, too. Hang in there😘

  • D.J., YOU TAKE REQUESTS? Please please wear tomato red with the pink blazer! I am visually thirsting for that combination!

  • Virginia M. Lowman

    I went through this phase about a year ago, when stopped working in magazines. I found that I transitioned from wearing somewhat bold outfits to clothing that was more minimalist. While it was very strange at first—my entire closet felt like it belonged (or should have belonged) to someone else—this newly forming identity also spoke to who I was becoming. Still confident, still eclectic, still very much me, but dressing for myself simply took a different form. Up to that point, I think I was following a formula that began as something for me and by me, but it became something by me and expected by everyone else, thus, no longer for me. Strange how that happens.

  • Une femme

    Leandra, I’ve found that my style/identity seems to shift about every 10 years or so. I’m 60 now. It may take me a few seasons to find my new groove, but it does happen, at least until the next shift. Relax, you have an inherent sense of style and what works for you, and it will start to click again at some point. The experiments (and mistakes) are part of the process. And they make for great blog material… 😉

  • kforkarli

    You look gorgeous in the white, pink and blue (and I bet Amelia would even wear that outfit!…so maybe it doesn’t scream ‘Leandra’?)

  • Giovanna Volpe

    So I am not the only one feeling this??? My boyfriend knows how I always open the closet and start to hate the world wishing to wear a white t-shirt and a blue jeans but no, I don´t find them easy anymore, so I star wishing to go out to the streets of Barcelona in mi pijamas! believing that I am who I am no matter what I wear.