The Best Fall Boots For You, Determined By Your Favorite Work Of Art

How do you choose boots for fall? By looking at them and being like: I like the heel on those suckers? No. You choose them by picking which of the below paintings you like best and then, on the next page, we’ll reveal a corresponding heel for you. This is also going to be a fun lesson in art. Pick which one of these pictures you like best and we’ll match it up with a good fall boot:

1. Andy Warhol, Gold Marilyn Monroe:

I like this piece because there’s something so lonely about it, as though she’s floating in a great expanse (perhaps that is what stars are supposed to do). Anne Boleyn once said she lived in a golden world, and this reminds me of that, too. Things did not work out well for her, or Marilyn. Or Midas.

2. Jean-Honore Fragonard, The Swing


Does she love the man at her feet or the man pulling the string?

3. Leonardo da Vinci, The Mona Lisa

I know, I know, you already know the painting. But it’s still great every time you look at it, right?

4. Francisco José de Goya “Portrait of Maria Teresa de Vallabriga, the Condesa de Chinchon’s Mother on Horseback

What is art? Why, it’s paintings of horses and sometimes ships.

5. Keith Haring, Untitled:

I remember reading a news article years and years ago when they asked a bunch of art historians why Keith Haring was so successful and they cited a lot of arty reasons and then they asked a kid and he said “his paintings make me feel really happy inside” and I thought that was the best reason.


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    • Shae

      That….actually worked? No, seriously. Have been obsessing about needing/wanting/coveting a pair of those lovely riding-style flat boots and BAM. #4 was my favorite painting. Didn’t even cheat.

      • Jennifer Wright


    • Nancy

      That worked for me, too! Fragonard and Kirkwood (GAWD I want those shoes so bad!)

    • Jen

      Is there a Mona Lisa boot version under, say, 50 bucks? Because I’m a cheap classics lover.

    • Lauren

      Wow, that worked for me too. Well done, Jennifer. You win the internet today.

      • Jennifer Wright

        Thank you. I will take the internet home with me and watch some Gossip Girl re-runs with it.

    • Lisa
    • Natalie

      But… I like Monet. What about Monet!

    • Kristina

      SO MUCH AWESOME. Definitely picked number 4. Definitely already have riding boots…. but now that I know I must have more riding boots to channel my inner WASP, I should go buy some more. When I ask myself later in the month why I do not have money for foodstuffs, I will remember that it is because Jennifer Wright read my mind and enjoy my ramen because all is right in the world.

    • Cate

      I am sort of surprised that I am a die-hard WASP, especially since I am not Anglo-Saxon at all, but I am very fond of both riding boots and Goya. So good job!

    • Lauren Lever

      You should have added some of those heel-less boots from Jeffrey Campbell, for Salvador Dali for some surrealist flavor.