In Partnership With
How to Style Ballet Flats

With zero dancing skills or physical coordination required


In partnership with Josefinas

Fact: If you can walk a mile in heels, you can judge whoever the F you want.

Theory: No one can walk a mile in heels without needing to take a walking break for the subsequent 24 hours.


Theory: Flat shoes never feel as exciting to put on as heels do.

Nor do they feel as exciting to buy. (Now we know, however, that excitement is beside the point when considering fashion consumption.)

Fact: There is 101% chance that every time you choose to wear flats over heels, the amount of fun you are capable of having, no matter the circumstance (though especially if you’re dancing), is elevated to the tenth power.

Unrelated fact: I am writing this from an outdoor restaurant in Rome, where incidentally it is absolutely not de rigueur to sit in the public domain chowing on tuna with your laptop open. People are looking at me like I’m on a treadmill in stilettos.

But I digress. Here’s my point: lately I have found that the less frequently I wear heels, the more insufferable they begin to feel. Yes, sure, they are fun to look at, hugely fun to buy and to style outfits with but when push comes to walk, though I never thought I’d say this, comfort is more and more becoming a priority. And you know what shoes come to mind when I think comfort? Ballet flats. And you know what the thing about ballet flats can be? They’re exceptionally tough to style into highly original! Unique! Quirky! Offbeat looks that don’t register as…the b-word.

That doesn’t make it impossible, though. Enter the self-bequeathed style-challenge to wear three different pairs of ballet flats — all by a brand called Josefinas — with three different outfits and call it a Lewk (capital L and all).

Like you got dressed in the dark:

Josefinas olive green ballet flats, Creatures of the Wind blazer, R13 shorts, Topshop socks

Go crazy! Have a baby! Only don’t. And when you look in the mirror and think, Man I look like I took an Ambien then kicked back a glass of wine or three when I got dressed, you’ll know you’ve done right by yourself. Sparkly socks? Why not. I was inspired by my husband, who wears calf-length socks with his shorts to exercise. A blazer that looks like nature on an acid trip? Yes. Duh. And a gold choker with flowers emerging from the back end? Nothing else says olive green ballet flats are da bomb more acutely.

Creatures of the Wind blazer, R13 shorts, Topshop socks, Lizzie Fortunato necklace

With a mini skirt:

Josefinas red gingham ballet flats, Reformation jean jacket, Miu Miu skirt, Illesteva sunglasses

This is possibly the most difficult pairing because an exposed leg is an exposed soul. And when we expose our souls, we become vulnerable. And we become vulnerable we lose our cool. And when we lose our cool, we cannot — cannot — wear ballet flats. Especially red gingham ones! So what do you do? You find a pair of sunglasses that are almost alienating because they are so not you. Then you put them on and work from there.

Reformation jean jacket, Miu Miu skirt, Illesteva sunglasses

With Jeans:

Josefinas safari (skin tone) ballet flats, 3x1 shirt, Levi's jeans, Lizzie Fortunado bracelets, Madewell bandana and lipstick by Chanel

This one is the simplest. You find a pair of ballet flats that are a color close enough to your skin tone, slap two layers of denim onto your body, accessorize with bracelets that may or may not double as small weights and boom: you’re French. But you speak English, so you can call any number of American hotlines and speak to representatives free of charge!

3×1 shirt, Levi’s jeans, Lizzie Fortunato bracelets, Madewell bandana and lipstick by Chanel; all ballet flats by Josefinas

Now tell me how you’d wear them and we can compare notes in the comments.

In partnership with Josefinas; Photographed by Krista Anna Lewis


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  • If I were a girl, or if I had small enough feet to fit into women’s shoes I’d definitely opt for wearing them with you jeans like your exhibit 3.

    Although I don’t understand the difference between heels and flats, I’m all about comfort dressing. I’d rather be comfortable than wear something just to “fit in”.

    Josh | The Kentucky Gent

    • BK

      Spend a day in heels and by 6pm I can guarantee you’ll have worked out how they differ from flat footwear

      • I mean, I have eyes so I can see how they differ, what I meant by my comment was that I don’t have personal, first hand experience of the difference. Sorry for the miscommunication.

        • Lua Jane

          They definitely make you feel different. It’s like a mental switch. For me at least. I have lots of gorgeous and crazy flats and wear them whenever I can get away with it, but heels are an ultimate confidence boost; I get few inches of height, my legs look longer, posture gets better, my stride is different. It’s like a shoe equivalet of red lipstick for me. If I feel like a girl before, after donning them I definitely feel more like a woman.

          • I have tried them and understand what you mean, but I can’t walk 10 feet without spraining my ankle!
            As much as I would love to wear heels once in a while, it’s a health hazard to me 😉

          • Lua Jane

            Walking in heels for me is the closest thing to athletic ability I possess. But I did start quite early, and went from Doc Martens ( gothic youth) to pumps. I do pack flats in bag just in case, if the heel is super high. No point wearing something that hurts too much.

          • Oh, but it IS an athletic achievement! Walking 100 meters in heels would be like running a 10K for me! Perhaps I should practice more, while trying not to break my legs. Good idea to bring along an extra pair of practical shoes, more gals should do that (sometimes I’m in pain just looking at someone hobbling forth in agony)!

          • Lua Jane

            Like a new born fawn taking first steps. It’s easiest to try to walk in them at home or at the office.

          • Awww, that’s such a sweet mental image, I’ll happily keep it in mind 🙂

  • that third look is so happening. (as soon as I get home from work and out of my heels.)

  • Stephanie

    Nice blazer! I really enjoy visit your blog. It’s such an inspiration everytime I visited your blog 🙂

  • Trainers are the way forward when it comes to flats 🙂 X


    • Hear hear! If I weren’t born with flip-flops, trainers would’ve been my first shoe choice 😉

      That said, I love the look of ballet flats; sadly enough, I still haven’t found a pair that fit properly. They’re either too wide or too long, my feet are weird like that.

  • I thought the title was “How to Style Baller Flats”

    I need a pair of shoes that can handle my 15,000 steps a day Fitbit lifestyle. Heels ain’t it

  • Love these ideas! I usually abstain from ballet flats because they can look a little too precious on me. I like the jeans look and the exposed leg look the best.
    xx Lane

  • Aydan

    So timely. This morning I was so disappointed when I pulled on my metallic silver flats (thanks JCrew), forgoing an array of amazing clogs, heels, and sandals in my closet. However, I did walk to work today and not having to carry heavy heels in my bag was def a relief on my poor shoulders! Long live shoes!! And long live flats!!…at least for today

  • Amelia Diamond

    Tru 2 size bb

  • kellymcd

    I find flats too flat for me and not in the “oh they lack height” way. I usually find the soles too thin and my heels hurting after a day of moving around. If I want flat shoes for comfort, I go for a sneaker or non-heeled bootie. Much studier and my feet are thankful!

    • Sally Waits

      Same! I find them so uncomfortable because they feel like they have no soles at all. Sneakers and booties all the way!

    • Yup, and they can result in dropped arches. If you’re doing this for health reasons… don’t.

  • Suzy Q

    Interestingly enough, I spent all my teen and early 20s in flats…to fit in. I felt so horribly awkward about been a 5’10” beanpole and I hated the comments about the characteristic that defined me the most: my height. I felt if I wore flats, I wouldn’t get the “you’re soooo tall” as often. I was mistaken.

    My feet do not take well to flats. Anything below two inches causes me immense pain and my ankles feel like they will slip out of their joins. And while I hate stilettos too, I’ve found my literal happy place in 3 inch block heels. I have an immense fondness for the work of Chie Mihara.

    I wish I could wear ballet flats without pain! These look cute!

  • Adardame

    I just can’t wear ballet flats. If I wear ballet flats the world will end. My feet need more distance from the ground. They must be cradled, supported, defended. Who knows when I might accidentally kick a cactus (true story)? I do not need to feel the pointy gravel scattered upon the sidewalk or the heat collected during hours of sunshine upon pavement. Perhaps if I were to walk always upon well manicured grass it would be better, but that frequently begets an overabundance of opportunistic mosquitoes. No, I will leave the ballet flats to those with more determination. I shall admire their stoicism from within my shelter, and say there goes a more stylin’ person than I.

  • Rhea

    The second look is way too cool! I love your style so much. I have mostly given up on heels this year… so I hear you!

  • Lua Jane

    Those olive green ones are gorgeous, but the styling of those tan ones is what I might go for. I have a habit of schlepping a pair of ballet flats in my bag on most days, while enthusiastically starting a day in pumps. I want the best of both worlds, the oomph effect of a heel, and the ability to actually walk distances, because walking is my favorite (only) kind of exercise. Where flat’s are concernes ballet ones are my favorite thing and have managed to acquire quite a collection by now. I am simply not a sneaker girl.

  • Connie
  • You’r wearing a portuguese brand. So nice 🙂

  • Brian

    Cute post. There are so many different brands of ballet flats in all different price ranges for every sized foot out there these days so it’s no surprise to me how they are being worn. I wear mine depending of the weather. Hot days with shorts and on cooler days with jeans or leggings. Because I’m a guy wearing them with shorts or skinny jeans can look a bit odd so my favorite way is to just have them peaking out from underneath my jeans. As for my favorite brand, it’s Tory Burch.

  • CarlotaLMorais

    You make anything look cool Leandra, I thought I didnt’t like ballet flats. But now I do ahah!! BTW JOSEFINA’S ARE PORTUGUESE! And so am I! So proud!!

  • Heels have their place and so do flats, just know when to give each their priority

  • ashleyclaire

    Do you guys ever do a thing where you help guide a reader who has fallen in love with a piece at the store only to come and realize she is flummoxed and doesn’t know how or with what to wear it? i’m hopeful!

  • hahaha Lov this article.

    My Fav is the denim look. Wish I had the gutts to wear the sparkly socks and the nature on acid trip blazer.

  • I sometimes feel basic for liking ballet flats, but I can’t help: they’re probably my favourite type of shoes. I wear them with pretty much everything, but I really like how you styled them, because it’s far from obvious. They work great with ladylike dresses when I want to feel really girly, but my favourite pairings are with boyfriend jeans or ripped shorts. And maybe it means that I’m getting old, but I started to appreciate investing in comfortable flat shoes. As you said – it’s not exactly exciting, but so much satisfaction afterwards!

  • MariaTeresa

    I’d wear ballet flats if only I had ankles. I’m 160cm tall and too lazy to convert that to feet. Basically my legs stop at a certain point where my feet start, without a gradual passage. It’s not simply “thick ankles”. It’s no ankles at all.

  • Fun post… I love my flats & low heeled shoes. I also need support but the old cobblestone streets in our town, I’ll slip on sturdy Clarks or a cute pair of ballet shoes (Bloch is my current favorite) and on my travels, a folding pair of Bloch ballet shoes are a must.

  • Ivan

    I really have small and narrow feet so despite being a young man I don’t have problems to wear ballet flats. I find them more comfortable (well in my opinion) that men close shoes but every feet is different. I like flats cause I can wear them with many different outfits and match them easily and look great as Leandra show us and at the same time being comfortable.The denim combination is my favorite but also the first one the olive green flats wit socks are super original !!
    I wear mine mostly with dressy pants and a nice shirt or with slim jeans and sometimes when is hot with bermudas ! By the way Josefinas flats look really good quality leather and comfortable !

  • Jess Harkins

    I feel this is relevant for me now that I’ve rediscovered ballet flats in the form of some bright red satin ones! I wear mine with blush pink culottes, or Levis (a la Leandra *push the sky*!). Colour is everything of course.

  • Tessera

    She said “You find a pair of ballet flats that are a color close enough to your skin tone” and then she showed a photo of herself in shoes close to her own skin tone. FYI: She did not claim that her shoes were the only possible skin tone.