How I Went From Hating Skirts to Loving Them
Photo by Edith Young

Skirts never felt right to me, yet I bought them each spring because it felt weird not to. They’re pretty, breezy, fun and flouncy. They paint a picture of who you in a skirt could potentially be. Most shorts, meanwhile, are practical in a boring way and crotch-threatening. You know what your thighs look like in denim shorts in pictures and it’s never how your thighs look in denim shorts in your head. Skirts always seem like the most fun option at the start of the season. But I’d put them on and spend the whole day wishing I could change into shorts or pants instead.

For about two years I gave skirts up. I stopped trying to be something I wasn’t and accepted that I was a shorts girl when it came to casually baring my legs. When you accept something about yourself in fashion, when you’ve determined a stylistic choice that says something about your persona or character — even if you don’t love it — it can be really hard to wiggle out of. It’s a rule that we set in stone for ourselves, like being in a crap mood no matter how much fun it looks like our friends are having over there, or telling everyone you’re lactose intolerant just because you said it once to get out of something and now have to live with the lie. It’s possible that I decided I didn’t like skirts one bad skirt day (a weird outfit, an unflattering cut, chub rub) then shut down any future thoughts about the ways my summer self could look in skirts. For two years I was convinced: skirts weren’t me.

Just as it gets harder and harder over time to remember why you and an old ex-friend no longer talk, however, I slowly stopped being able to remember what it was I didn’t like about skirts. I tried them here and there. Fall felt like a safe time to experiment because of suede and layers. By May, I began to notice I suddenly had clothes — out of nowhere! Skirts, man. Who knew? The revelation invigorated my closet. (I also bought a few new styles and donated some that were totally off the mark, which is important to note; it’s possible I was wearing “the wrong ones.”)

For the past month I have tried to wear skirts as much as possible. Any time I’d normally reach for jeans or shorts, I have a pep talk with myself, then grab a skirt. The skirt forces me to think a bit more creatively about my outfit, because tops with shorts or jeans are a whole different story. I have to find new ways to think about balance, colors and proportions. If it sounds dramatic, that’s because I was being dramatic, but I was entirely out of my comfort zone.

Which felt great. I’m wary to say what kind of person I am or am not when it comes to clothes because clearly, this person is fickle, but right now, I’m into being “more of a skirts girl.” The acceptance feels like a breeze blowing ’round my nether regions.

Feature image by Edith Young; skirts documentation via Amelia Diamond. Georgia Alice skirt in feature photo.

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  • Amelia, you look fabulous in a skirt. All of them. No, you really do!
    Funny, but as an owner of quite a few never-worn skirts, I do skirts (and dresses) mostly in the summer – with relish. Come fall, I really don’t want them.
    And while I don’t look as good as you in a skirt, I still manage to feel great, thighs and all.

    • Amelia Diamond

      dressess!!! i need more dresses!

  • Abby

    That Fleur du Mal skirt is officially my everything. Maybe it’ll go on 90% off sale!

    • Amelia Diamond

      hahaha I am waiting on the same thing

  • Weronika Michta

    Glad you’ve joined the party!

  • me

    Sis, you look freakishly awesome in these pix ! So glad you were wrong about not being a skirts girl ….

  • ♠ gloria cook

    I’ve been going through the same phase with skirts. I always thought they looked terrible on my because I’m not very tall, and I hate heels. They are certainly a style challenge! Your skirtfits are inspiring, and I feel honored because I was eyeing up the same Stella McCartney skirt on The Real Real 😄

    • Amelia Diamond

      ME TOO I AM 5’3 AND THINK THIS WAS PART OF THE PROBLEM. I just wear my skirts kinda short now!

  • Leonie

    love the shirt you wore with the reformation skirt 🙂 is that the same logo as the thigh-chafe stick company?

    • Amelia Diamond

      yes!!! i just asked her where she plans to sell them.

  • Andrea Raymer

    I think we just switched mindsets. I was always a skirts girl. I could rely on an a-line skirt to make my legs look thinner and I had a whole system to deal with the thigh rub ( Spanx+Dove deodorant every single day). I hadn’t purchased a pair of shorts in 5 years. This year, though is the year of the short for me. If only I could wear them to my office.

    • Amelia Diamond

      shorts = your weekend party pants!

  • Frieda

    Frankly I love all your skirt outfits. Like “what was she thinking – skirts and her are made for each other – q.e.d!” 😀 congrats gurl, you made me look for skirts at summer sale now

  • Victoria (Tori) Inge

    I felt the exact same way about blue denim – I strictly only wore black denim. However a year and a half ago I decided to delve into the land of the blue and how I have more blue denim than black – although I am VERY picky about the wash!

    • Amelia Diamond

      isn’t it weird one day you’re just OVER the mental block!

  • Ramona Flowers

    well, I really love skirts after reading and seeing articles about celebs wearing them in The Beauty Insiders, Skirts are really the best, it feels fresh and freeing! but yeah you would really have to act pretty lady like as you need to prevent your lady parts from showing to the public right?

    • Amelia Diamond

      i am just careful about exiting cars

  • Carrieanne Luicadi

    The Georgia Alice skirt might convince me to wear skirts. Its so perfect!

  • That yellow Georgia Alice skirt is just gorgeous! Looks great on you Amelia.

    • Amelia Diamond

      thank you! it’s all the skirt

  • you look gorgeous !

    • Amelia Diamond

      bless you!!

  • Blakey

    Megababe shirt so cute. Also, need to know, do you skate as image four clearly suggests?

    • Amelia Diamond

      Gah I know she needs to sell them I just bugged her about it. ALSO NO I DO NOT I AM AN ACCIDENTAL POSER. This is one of my best friend’s little sister’s boyfriend’s skateboard that has lived in my apartment by accident/out of laziness for 3+ years. (I am >< this close to buying a longboard though)

  • Haley Nahman

    You’re making me want to wear skirts!!!

    • Amelia Diamond

      you make me want to be a better person!

  • I used to be this way with dresses. Then I realized that putting on a dress meant I didn’t have to worry about matching or tucking or shimmying. One garment covers all the important parts, throw on shoes and I’m off!

  • Jacqueline Ho

    I completely agree with this article! I had the toughest time implementing skirts into my wardrobe until this year and I feel like it’s adding so much more color/patterns in my everyday wear. Still trying to get the whole proportions down with a skirt and a top, very different from jeans/pants and tops!

    I’m glad i’m not the only one who feels like this, everyone at work questioned my dislike of skirts for the longest time and didn’t understand my love and the ease of pants!

    • Amelia Diamond

      i wanna see some of your skirt outfit ideas!

      • Jacqueline Ho

        I typically feel that a solid top tucked into a patterned skirt is a safe way to go while I’m experimenting with wearing skirts.
        I also treat skirts as high waisted pants so I sometimes wear a crop top with it

        I have a knee length and midi skirt and an ankle length. I realized since I’m petite, ankle length looks a bit odd on my body and I’m opting out of those. But it was a floral print skirt for $5 at urban outfitters….how could I pass on that steal!!

        I have yet to experience with pattern on pattern, but I love how you styled the Georgia Alice Skirt with something floral. Something I have yet dared to do!!

        I’m glad we are on the same skirt journey! Happy skirting!

  • Paula Rodio

    You were born to wear skirts!

  • OK this is like, THE INSPO post of the summer. Love every single outfit and am inspired to wear all the un-touched skirts in my closet