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.


1. If you love Andy Warhol, you want something more modern. Something with a little edge to it, a little glitter, but something still accessible. Something with gold elements.

These. Schutz Shoes, $230.

2. If you love the totally impractical, peasants-gonna-get-you romanticism of Fragonard:

Nicholas Kirkwood, $1,695

3. You like the Mona Lisa? You like things that are absolutely classic. Let people call you boring. Those people can’t truly appreciate the way those things feel familiar, yet, when you stare at them, you realize they are familiar because they are beautiful every time you look at them:

Coclico, $555

4. You die-hard WASP, you. Let’s go beagling together.

Saks, $598

5. Colors and light and a little element of whimsical cartoonishness make us all feel happy inside:

Shoes of Prey, $330