I’ll Never Let Go, Strap: How to Wear Sandals this Fall

The answer isn’t socks. Boom!


Does it ever happen that you will have owned a garment or accessory for a number of years and then find that even though you’ve liked the thing for as long as you’ve had it, you also never thought you couldn’t live without until boom: it’s the only thing you want to wear?

This happened to me at the end of the summer with a pair of lace up sandals akin to these but handmade in a small shop in Southampton Village on Long Island at a store called il Sandalo. It’s like August reared its head and all of a sudden all shoes are useless lest they lace up my leg, and all feet are useless lest they fit inside these shoes. I wore them with vigor. Often with slip dresses but also with shorts and sometimes just bathing suits and this one time, with nothing else at all (I was streaking through the quad).

What’s happened since September 23rd officiated The End is that I’ve realized they look pretty great with early fall-centric clothes, which brings us to right now and here, where I am trying relentlessly to hold on to the last standing slice of exposed skin and plan to do so until my toes are purple.

Let’s discuss.


Here is exhibit A — a pair of high waist blue jeans plus shearling and embroidered trim and a leopard print coat by Shrimps plus light blue fur collar to evince the spirit of a funky fall but not without first pledging allegiance to the season that came before it. In with your shoes, out with your shoes, right?

I don’t even know what that means.

Shrimps jacket, Toga jeans, Edie Parker handbag, Céline sunglasses


Here we have a pair of culottes that could conceivably double as a mid-length skirt which is once again all the rage for raging shown in a utility green paired with a pink jacket because newsflash, humanity: black is the color of a dark soul and thus should not be reflected in the vivacious life you try to embody through your garments. All hail the return of color!

Roksanda jacket, Vilshenko culottes, Rebel and Crown t-shirt


And finally, some bell bottoms. I don’t need glasses because my eyesight is pretty good but ever since we publicly proclaimed our (as in, Man Repeller’s) affinity for Lucy Chadwick, I just can’t imagine a reality where I am not wearing specs on my face. Also hard to imagine living on without: a red mock-neck sweater that once belonged to Paddington Bear. And tilt-a-whirl pants! This works because the sweater is so warm, my body will basically need the fresh air that my toes will command and just like that







Rosie Assoulin sweater and pants, The Row handbag

Photographed by Krista Anna Lewis


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  • oh man those bell bottoms are SICK!

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  • Only people with pretty feet should wear sandals. Hairy, dry toes are not a good look man or woman!! 😉


    • Leandra Medine

      my toes are hairy! <3

      • My therapist will invoice you. 😉

      • BK

        Haired toes of the world unite

  • Morning, Leandra! Do you think I could borrow the red Rosie pants? Just for a day. Thanks!

    • ya then me plz thnx

    • Krista Anna Lewis


    • Leandra Medine

      for you? anything.

  • omg. shrimps jacket. rosie red dynamic duo????? Favorite things. I am sold. U stylin’.

  • Jackie

    In love with look #2.

    • Nora

      I wanna be next in the red-Rosie-pants line!

      • Nora

        That was supposed to be a reply to Emma!

  • Natali

    Superb and such an inspiring outfits, all three of them, 2nd one being my ultimate favourite!


  • Y.U.P NYC

    Yasss, yasss, and yaaassss!! All those outfits are to die for, especially your last OOTD with the bell bottoms. And everyone thought I was crazy for hanging onto my high school flares lol!


  • Lucy

    These shoes deserved a post of their own and I’m so glad you obliged.

    The best part is that they aren’t super “unique” or even “man repelling” in the grand scheme of things, but when you pair them with Rosie pants, they work.

    I didn’t want to buy the recently insta-famous 3×1 cropped fringe jeans because they were, well, overly insta-ed.. but my friend smartly commented ” don’t think about being different! Think about being you! You can be different by how you wear them.” <<< duh, and the argument works for these shoes as well

  • Loonia Ali

    Beautiful looks! Love all!

  • Dawn

    Love every last one of these looks–and I couldn’t agree more about letting your toes be free! as long as possible.

  • I love wearing open toed shoes year round, as long as there is no snow.


  • Just moved south, so Imma give this a shot. Let those phalanges shine!

  • Morgan

    What brand are the shoes!

  • Pam Gregoriadis

    Dear Leandra: almost totally unrelated to your post, but it is because of you that I now dress well every day and don’t bother with makeup. Often, I would opt for the easiest thing (jeans + t-shirt) because I thought I had to, you know, do my makeup also and I couldn’t be bothered. And I say *almost* unrelated because this post has me thinking about the possibility of wearing sandals throughout the fall, altering my former approach. YAY.

  • Esty Turner

    Hey Leandra! Where’d you get your Israeli flag bracelet?

  • Really nice outfit! Love your writing angles!


  • Anonymous

    That flag on the wrist is disappointing.

    @disqus_5FsM4qENMc:disqus hope you know about the barriers to peace in the Israeli- Palestinian conflict before getting one.

  • Leandra, in that last look you are so channeling a high-fashion Velma. Plz solve mysteries with me Scooby and the gang. We can wear neck scarves, too!

  • I am LOOOOOVING those sandals with the culottes. Bravo, lady!

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  • Jel

    Ahh, I want to live in the outfit with that pink jacket.

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  • Elsi Ferris

    but who makes those clear frame glasses?! need em