What Happens When Your Style Stops Evolving?

Sometimes, when I’m walking down the street, I see women dressed in commuter shoes and blazers with huge shoulder pads, or with really pouffy bangs and faint blue eyeshadow, or in black platform sandals and skinny jeans and a waist belt with lots of gold chain necklaces. Then I look down and observe the utility jacket over my shoulders paired with high-waist denim cutoffs and ballet flats and think to myself: Do women reach a style apex at a certain point that they just can’t recover from? I say recover because it’s like we get stuck in an era that we believe both defines our “truest selves” and also encapsulates a heyday.

When I discovered utility jackets and reworked Levi’s denim shorts in 2009, I legitimately underwent a transformation. Suddenly, I had ALL THE CLOTHES I could ever need and thus just had to figure out footwear. I was also 21 and had launched Man Repeller in tandem with graduating from college, was about to get back together with my asshole ex-boyfriend who then became my really nice husband and all of it made being alive so much fun. Everything was new! And changing! In a good way! My 20s were off to such a cool start. Look, it’s not like I’m inching towards the end of them while grasping for the inside of a garbage dispenser, but a lot of life happens in your late 20s, which no one had told me about before I googled, “why are the end of my 20s so hard?” (Saturn rising, apparently, but also, you start to realize things you don’t like about yourself that have always been true but which you never previously acknowledged or recognized.)

When I settle into a pair of jeans and reach for my utility jacket, I think that I’m trying to recreate my early 20s. That makes me feel like Regina George’s mother in Mean Girls, who just didn’t get that she wasn’t her daughter’s peer. The thing is, though, I don’t even want to go back to my early 20s. I was so confused and unsure and spent most of it feeling like I was in the process of emerging from the birth canal. I’ve been mentally ready to grow past my former self since I first wanted to start trying for a baby (and if not then, definitely last August when I bought my first pair of sensible trousers). Is it weird that my style hasn’t technically changed to reflect that? That I could still want to look like a former version of me, even though I don’t necessarily want to feel like her? Could I simultaneously feel, on the one hand, this intense sense of imposter syndrome when I wear clothes that are indicative of a former me, but on the other, completely self-understood? Is that feeling of self-understanding actually just my comfort zone?

It’s all so confusing because here I’ve been operating on the premise that style is a reflection of where and who we are in real time. Like a mutable appendage, or temporary tattoo. But maybe that’s not true at all. Maybe the magic is in the tension unwittingly created between who we are and who we were.

For what it’s worth, I am eager for warmer weather — not to wear jean shorts and utility jackets, but more because I’d like to wear caftans with close-toe, flat slingbacks and a plastic basket. Does that say anything?

Photos via Leandra Medine; feature photo by Edith Young.

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  • Babs

    thoroughly enjoy this time travel. also, AGREE. I’ve actually been feeling this weird stress lately about arriving at a good look/style identity quickly, so that if I get stuck there, it won’t be so bad. Spend your thoughts elsewhere, Babs, I say! It’s like getting dressed for my funeral or something.

  • Well, you do look great in it, so there must be something there 🙂 Are there no other … signature outfits that you’ve worn again and again? And maybe more will come, but not too many on the whole. And all the other stuff inbetween.

  • Adrianna

    Today, I’m wearing the studded leather jacket I wore all through high school since age 14. I’m 28 years old. The forearms of the sleeves are so worn from use that the leather turned to suede. I still wear the utility jacket and bomber jacket I bought when I was 15 or 16.

    Is our style supposed to change? Or is it a pressure we feel when the fashion industry tries to sell new clothing every season

    • Meg S

      The challenge with personal style is to find new pieces every season that still feel like you. I’m getting better at is, but sometimes I buy something that’s just weird and doesn’t fit in with my usual style. I chalk it up to the usual risk taking that happens in fashion, and it doesn’t always work.

      • Adrianna

        In some ways current trends helped me achieve my style. I spent all of college scouring ebay for leather motorcycle jackets. You’d think one would be easy to find given that every single 20-something woman in NYC seems to own one in 2017.

        • Meg S

          I discovered my love of bomber jackets within the last year. I bought several and throw them on over whatever I’m wearing if it’s chilly outside. I have one to go with pretty much everything. Now that you mention it, I don’t have a leather motorcycle jacket. I have moto jackets in lighter fabrics, but I think a leather one is a staple missing from my wardrobe. Time to hit up ebay, I guess.

    • Hellbetty666

      I still wear band shirts – those from 20 years ago and more recent ones. I always wear boots and for work I favour separates, but within those parameters I would have said my my style has always changed. Now I can’t work out if my style/taste is evolving (or at least changing 😉) or if I’m the same as I was in 1990.

      SO many questions!

      • Adrianna

        My formula is essentially the same, but cut of jeans changed from early 2000s flare/boot-cut to late 2000s skinny. I essentially reverted back to my adolescent taste now that I’ve worked in a very casual office for three years. Now that I’m no longer in my early 20s, I also no longer feel the need to use clothing to be taken seriously. I’ve been wondering if I’m starting to look outdated/old when I see younger girls wear those weird baggy crop jeans.

        • Hellbetty666

          I feel you. I’ve also had that worry I look like an eccentric auntie. I never got the skinny jeans thing so I’ve worn bellbottoms/flares/wide leg trousers continuously since 1992.

          However the great thing about getting older is worrying less and less about other people’s opinions 🙂

          • Heather Chambers

            But eccentric aunties are the BEST!
            It is my life goal to be an excellent eccentric auntie.

      • pamb

        One of my greatest regrets is giving away all the concert t shirts (baseball style) my my youth in the 70s-80s. I was too mature, you see, as a college student, to wear a Journey t shirt.

        They wouldn’t still fit me now, but my kids would look cool!

        • Hellbetty666

          That’s devastating. I feel like that about a Topshop maxi dress in a patchwork print which I paid ten pounds for in the sale. I went off it. Couple of years later, I was like “what the fuck?!”. Twenty years later, I still feel vexed.

          I have kept all of mine mostly because I still wear them, but there are a couple I’ve lost along the way that have broken my heart. Hopefully someone is wearing and loving your classic rock shirts right now

    • Alison

      “when the fashion industry tries to sell new clothing every season.” Yes. That’s exactly how it feels. It doesn’t help that I can be a size 4-10, like Christina Topacio
      describes here:

      I came into my style in my late 20s/early 30s. I have yet to meet a bright colored dress or a pattern that I didn’t like. But I’ve had a hard time finding clothes in the last couple years of sheer/nakeds. It feels like everyone is trying to sell clothes that are going to fall apart within a few months.

      • Adrianna

        This is different from Christina’s point about the industry, but I do find that I have a more narrow sense of style every time I feel I’ve gained weight. I acquired a wide range of clothing after I went from an American size 10/12 to 2/4.

  • BarbieBush

    awwwwwwwweee cute 2012 Leandea *feels*

  • Meg S

    I find myself going back to more grown up versions of my favorite clothes from years gone by. Instead of cherry red docs, I’ve upgraded to a black chelsea style. I’ve never ditched the converse – these have been a staple in my wardrobe since I was in high school. I fall back on a more grown up version of jeans and t-shirts. Trends come and go in my wardrobe, but there are some classic pieces I fall back on.

    • Paula

      Converse… shoes for EVERY member of the family.

      • Meg S

        Yes. One of my nieces wears converse. I’m trying to get the rest of her kids to do it too. There are perks to being the cool aunt.

        • pamb

          Please explain Converse to me! I had one pair, and I felt like I was dragging a platform around… just not comfortable.

          • Meg S

            I’m not sure I can explain them? Maybe because I grew up wearing them, I think they’re super comfortable. They might just not be the right shoe for your foot.

  • Nico

    I appreciate this article a lot especially bc lately my husband has been telling me I need to retire my old utility jacket. It’s the perfect neutral lightweight jacket and if I do “retire” it, you can be sure I’m just going to find a new similar one to replace it.

    That being said, I was also at a women’s panel the other evening and about 75% of the room was wearing a version of the utility jacket and almost 100% of the women were all dressed in neutrals. What does this mean?!

    Still looking for a new utility jacket..,

    • Hellbetty666

      Can I ask what condition your jacket is in? If it doesn’t need replacing I’d not get rid – it sounds like the perfect thing! Maybe add a patch?

      • Nico

        It’s totally fine! Ha. I think he maybe thinks I could update the style of it if that makes sense….it’s a pretty basic J. Crew/Madewell style utility jacket. I’ll prob just find something similar but with a slightly more current shape or details…sort of exactly how Leandra has a few diff ones..

        Patches are a good idea though!

        Leandra – who makes the jacket you are wearing in photos 1 & 2? Love that one…

  • Linda

    I mean, does your style HAVE to evolve? Does it mean that you are not evolving just because you are wearing the same style of clothes?

    I am not sure about that…

    Scrolling through the pictures, I feel like it has been your style all along just looking more like you in the last few years. That omnipresent maximalist attitude, you know?

    As you said, in our early 20s we are unsure, confused and so stressed about being “authentic” and worried about giving people the most accurate representation of our true-self. But then, at least in my case, little by little I was learning to let go and finally thought “fuck it” and I did me regardless of others interpretation of myself. And guess what that “me” is very much similar to the girl in early 20s just with less fuck given and more scarves tied around her neck.

  • Amelia

    “I don’t even want to go back to my early 20s. I was so confused and unsure and spent most of it feeling like I was in the process of emerging from the birth canal.”

    I’m in my early/mid 20s and that is the most accurate thing i’ve heard all day.

  • Maria

    Oversized denim shirts are my utility jackets.

  • Perry

    It’s not the clothes that need to evolve, it’s the people wearing them. Designers discuss seeing the person behind the clothes and not the other way around.

  • Slushee

    Well I’m 40, and I realise I’m there – in the sense that I’m wearing stuff that feels like me and not someone else. And the elements are consistently the same. Sure I introduce bits but the elements, the silhouette is consistent. Peace!

    • Hellbetty666

      You’ve hit the nail on the head for me – “stuff that feels like me” perfectly describes the basis of my style: comfort. And the silhouette tends to be pretty similar too. It’s the details that make all the difference imo.

    • Same. I’ve always dressed to reflect my personality, so for me, that means no dresses unless it’s for occasions. The elements have always been the same: jeans, sneakers, T-shirts, but the difference now is the quality. So instead of canvas Converse I now wear Italian leather sneakers. Instead of Hanes, I wear higher-end T-shirts with more drape.

  • Hellbetty666

    Does our style ever really stop evolving though? I know what suits me and also what-doesn’t-suit-me-but-I-don’t-care. Within those parameters though my style is always evolving. I’m sometimes a bit jealous of people who have found their look and stuck with it their entire lives.

  • Abby

    My style literally hasn’t changed since I was 16. I’m fine with it.

  • The Frockstar

    I still crave those Christopher Kane denims. 👌🏻

  • Alyssa Renteria

    hey Leandra what utility jacket are you wearing? Im in need of a new one, and I love the one who have on ??

    • Leandra Medine

      It is Anine Bing!

  • Andrea

    From what I’ve observed, for women in their 30s, there seems to be a huge range in terms of who looks younger/older/on point. The biggest factor is not wrinkles – it’s being “stuck in their era” as my sister calls it. Hairstyle (especially colour), denim choices, and clothing that reflect their “prime time” (aka a modified version of what they wore in their 20s). You can have the flawless skin of a 22-year-old, but if you haven’t updated your hair and makeup looks or you’re still wearing the same style of clothing from 10+ years ago, you do end up looking older than your peers. I’m not saying this is a bad thing – wear what you want & like, please! – but it does end up aging you if you don’t update the way you wear those favourite pieces or you’re still doing the same thing with your hair that was a big trend in 2003.

    • Paula

      Yes, this is absolutely true and I see it in some friends who haven’t updated their looks. I was also reading another article elsewhere which said keeping your hair style the same and your hair colour “natural” keeps you looking younger.

    • pamb

      I have a FB friend who is still wearing her hair the same way as when I met her in 1988 (I am old). It looks like the same lipstick color, too. I guess it works for her, but…

  • Unrelated, but what is a plastic basket? I’m intrigued!

  • Daniela

    Leandra, your style does evolve! You are just more and more stylish every single day 😉

  • Ana

    So, totally agreed, most of us have staples that make us feel like ‘ourselves’. Love how you and your utility jacket have evolved stylistically, Leandra! I am also on team converse, and resort to my good old grunge mode when I crave a sense of self. But can we truly hang on to a style that is tied to a time and an age? (my ‘peak me’ was at 17-18) and now, in my mid thirties, with a different body, I wonder if I can really still get away with dressing like a slightly more sophisticated version of my teenage self. I don’t want to use the term ‘age appropriate’, but does there come a point when you have to say goodbye to a self-image that literally doesn’t fit anymore? I’ve given most old staples away, but there are a few ghosts in my closet that embody the sadness of outgrowing the promise of being able to pull anything off (i.e. of being truly young). And are the old, loved textile friends really what make us feel like ‘peak us’, or are they just the material reminiscence of what it felt like, in those rare moments, of feeling invincible? Will a Chanel jacket and a string of pearls ever make me feel as awesome as my f****ed up utility jacket and a pair of docs?

  • Diana McNeill

    This legitimately sounds like something Carrie Bradshaw might write. And I kind of love that.

  • Mo

    Scrolling closer to the bottom, I wanted the answer. Soaking in words and problems and hoping that at the end, you’d found it. That you could explain to me that feeling of both accepting and rejecting the self. But, that is the symptom of the late 20s, yes? The uncertainty. The continual answer that I do find through my constant questioning seems to be that all there will ever be is a question. All I could ever hope for is the continued desire to know more and to understand that no one knows or has known anything more than me, its just the individual experience. And maybe its a bit appeasing for some to get stuck in the lull of having one of their questions answered, to not push themselves any farther, because they are safe there, with that self and her wardrobe and her identity. Safe with the familiarity. But for a Man Repeller, the self, and the wardrobe, will always fluctuate as long as there are questions needing to be answered.

  • Jessie Erikson

    I think there’s kind of two evolutions you’re the asking about here – one is about you and your big formula… but the era thing is more about details. Like you can still have blazers be a cornerstone without big shoulder pads. Details always define the decade – the way 90s blouses or button ups always have weird things like the top part of the shirt doesn’t really button and is angled to be ~feminine~ or something. Those are the things to pay attention to. And some stuff is really more resistant to this I think. As for your utility jacket – I guess it’s not enough time to know, really. We will have to see how it differs from the next incarnation of utility jackets, not how it differs from whatever OTHER jacket style may be more in style at the moment.

    As for style evolution, my style mostly changes when my lifestyle changes. Usually I’m pretty resistant anyway but you just can’t wear the same things everyday when you work part time in retail as when you are in graduate school, unfortunately.

  • Summer Lotus

    Leandra Medine touches some interesting concepts in this article. I’m lucky in that I’m part of a women’s dance community, and I get to interact with ladies from mid-teens to their mid-eighties at least once a week. My dance teacher and mentor is in her mid sixties while I’m a late twenties. If there’s one thing I’ve learned regarding “style” from this huge range of people is that clothes are, well, just clothes! Clothes are just one way of expression. Bodies change constantly, but people like certain aesthetics from all decades of their lives–and that’s okay! The idea that there’s an “age” to the fabric you drape your body in is a complete social construct–none the more apparent when you have “decade revival” on the fashion runways (looking at you, 90’s revival!).

  • Cynthia Schoonover

    I’m in my early 60’s and my style is still evolving. As you get older, it’s important to update your hair style and make-up, and realize that even if you have a trim figure, you can’t dress like a teenager because it only makes you look older.

  • Jill

    I used to mix it up a lot, in my twenties and into my early thirties. Now that I’m approaching 25×2, it’s a little different. The body changes (even if you stay fit), and clothing just isn’t really made for you anymore (or for most of us). It’s still very much youthculture. And I feel like I’ve actually gone back to where I began…which was in the late 70s, and early 80s, as a young girl, when the things I wore just made sense. jeans, fun tops, wedge sandals, (though I have NOT abandoned my fun heels at all), tank tops and skirts, simple dresses…it turns out that how I dressed as a kid (and to some degree as a teen) really suits my life now. I have my summer and winter uniforms, of sorts, and then I add fun accessories (and for me, shoes fall into the accessory category). I wear more color than most people I know – I love color – but otherwise the clothing “basics” are all I need. As long as I have the accessories. 🙂

  • Stacey

    More and more I realise that I like certain cuts and colours because they make me feel comfortable and I like the way I look in them. My body shape hasn’t changed a lot either. So a lot of my clothes I keep rewearing or rebuying the look. I go through my cupboard every so often and reassess what I love and donate what I’m not wearing anymore. I use accessories to change the outfits up. I do need to remind myself to try a different cut or colour every so often. Usually I don’t love it, but it doesn’t hurt to try…

  • pamb

    Ladies, I don’t want to scare you, but my style stopped evolving when I had my second child, quit my retail job and moved to the suburbs. Throw in moves to two different states and I’m still digging out fashion jewelry and saying “I forgot I had that!”

    My winter style is classic pants/top/cardigan with a statement necklace (not huge and garish, not too many multiple chains). My summer style is the same, with a knee length skirt swapped out for the pants.

    My outside says Suburban Mom, my attitude says I’m Looking For More Than My Town Can Give Me. Let me lose enough weight (this time is the charm!) to fit back into some of my former wardrobe (I have some great things) and we’ll see if it evolves again.

  • C. Killion

    Sure, we evolve…and we carry forward with us the styles and clothes that love us back, as much as we love them. Doesn’t mean we can’t discover new treasures, just means we have sure go-to’s when an a surprise trip to the ER with a skateboarding kid happens. What would I do without my topsiders and my jeans? For a business party I can pair a sequin top with a pair of silk palazzos I’ve had around for years, and viola! dinner out! Life is good.

  • streats

    “style is a reflection of where and who we are in real time.”

    Yes. I really find that my style reflects my current feelings and place in life right now. When I was struggling with burnout and difficult work relationships, I wore a lot of hard leather, chunky stompy boots, and soft jersey pieces that made me feel strong/armoured and comforted/protected at the same time. When I quit that job and found myself enjoying a new lease on life, I started wearing a lot of light colours, natural fibers, sheer, floaty silhouettes and sporty pieces. When I went back to school and worked two jobs, my insane schedule led me to a uniform of black jeans, men’s tshirts, and sturdy Chelsea boots. Now that I’m figuring out my next step and opening my mind to all opportunities for where to live, where to work, so too am I opening my mind to all kinds of styles and influences and silhouettes. It’s fascinating and I hope I never stop evolving.

  • isn’t “having style” just knowing what you like to wear ?
    I’ve been wearing black for a while, as a uniform and switching shoes + accessories as much as I can to spice things up. And that’s it, I think I’ve found my style. Also, I’ve watched “the true cost” which mad me realise that I didn’t want to buy into fast fashion any more and since I can’t afford YSL as much as H&M then I just buy less and settle with what I have. ie. : goin on holiday with a carry-on 😉

  • Leah

    You read my mind! I just hit 29 and I wondered if, when I turn 30, I’ll finally change my wardrobe, maybe to something that finally reflects my age? I found my style formula at about 22 years old- straight leg jeans, japanese sneakers, my boyfriend’s sweatshirts and bomber jackets (I have about 6 different bombers). It has carried me all through my 20s, but can I pull it off in my 30s? But if I ever try to change it up, wear shoes, a smart jacket etc, I just don’t feel like me! Only time will tell I suppose

  • Catherine Mardosa

    “style is who we are where we are in real time” yes with all the ways we are wrong about who we are and where we are and how beautiful that inaccurateness inevitably is

  • B

    I’m only just about to be 21, but I have literally been wearing the same flannel shirt and same pleated wrap mini skirt since I was 17. It struck a chord when you said that maybe you were trying to recreate your early twenties, as I was just having a conversation with my best friend about the patterns I’ve been repeating since high school, and like you said, learning that there are things I don’t like about myself that I never really thought about before. (I love run on sentences and I will not change unless being paid to do so.) Anyway, how do I let go of these patterns, how do I rectify these qualities I formed while wearing those same clothes?
    I wore jeans/pants in public for the first time since I was 17 today. I wouldn’t have if I didn’t start reading Man Repeller like, yesterday because apparently that’s when I decided to be born.

    P.S. I’m saving up for baby’s first leather jacket.

  • Well, I just added to my utility jacket collection by buying a utility VEST. At Target!
    The problem with personal style as you age, at least from my perspective at 50-something, is your body and face is constantly changing. I think I accepted my appearance and felt I knew who I was and found clothing and accessories that presented myself truly for one hot minute sometime in my twenties. (But then, that is also completely a lie, since I also remember feeling like I was a complete phony then too.) So, personal style is for me, a way of communicating who I am inside, and that person is in many ways the same person even as my outer skin-shell looks different. I was Me in my utility jacket in 7th grade, and I am Me in my utility jacket now.

  • Taylor

    I’m only 23 so I probably haven’t hit this point yet, but, I know for sure I’m not giving up skinny jeans! When everyone said the skinny was out I just stared at my friend and said “they can’t do this to me….”

    To me it’s the most flattering cut. After that I like straight leg, but I don’t think I’ll ever touch bootcut again….

    I do feel like I’m in this weird middle though we’re I have to be an adult for work but when I’m out I’m in crop tops and denim shorts. I start to think, am I too old for this? Have I aged out of crop tops yet and big funky earrings? Do I have to stop getting obnoxiously long braids?