Lethal Landscaping: Seven Surfaces that Scare the Stilettos Off Every Fashionista

Recently, as I walked gingerly on the brick pavers between buildings at my real job—in five-inch Michael Kors platform stiletto sandals—it dawned on me that our urban landscape (which is often a feast for the eyes),  is murder on the feet. Or the shoes. Or both. Fortunately I mastered the pavers that day, and historically speaking, my feet, shoes, and ego have fared well despite challenging terrain.

Even as I traversed unscathed, it was a momentous occasion, for I suddenly realized that I am not only frequently at war with the ground under my feet, but that I spend an inordinate amount of time contemplating my choice of footwear. And not because I don’t know what to wear. That’s easy. Gimme a heel, and the higher the better. No, my contemplation, my rumination—my anguish—are all because of the list below…

Seven (Almost) Deadly Landscaping Sins that Scare the Stilettos Off Every Fashionista

  1. Gravel. Nothing like trying to balance on the balls of your feet, on an uneven, moving surface…while also trying in vain to keep the dust off your shoes or out of your sandals. Gravel is murder on your car, murder on your heels upon exiting. I say we abolish it, stat.
  2. Cobblestones/brick paved-walkways. When I think of cobblestones, I always think of one of my favorite southern cities: Charleston, SC. Cobblestones and brick pavers are a pricey and lovely addition to any landscape; quaint, but lethal in platforms. There is nothing worse than attempting to stride confidently across a very public walkway, then suddenly you have that wobbly, I’m-not-quite-sure-if-I’m-going-to-eat-it feeling. You know many a model has eaten it on the runway in crazy-high plats, and they’re walking on a flat surface. Oh, the horror.
  3. Cracks in sidewalks and decks. What’s that saying? Step on a crack, break your mother’s back? How about step on a crack, break your $700 stiletto. Or permanenly shred your leather/suede/stacked wood-covered heel. My nemesis.
  4. Uneven, cracked pavement. A nasty combination of numbers 2 and 3. Precarious in platforms, portentous in pumps. Add rain and all those dips and cracks become puddles—or another way to ruin a nice suede boot when weather forecasters lie.
  5. Steep stairs. Tough (especially in heels and a narrow pencil skirt), but not so worrisome when ascending. Descending? Suddenly, I have a fear of heights.

    Even more terrifying: when stairs are gleaming marble and you’re in five-inchers and no where near a handrail.

  6. Polished concrete. Yes, it’s so urban, so cost-effective, so Home Depot. So not good if there is a drop of moisture and you’re wearing a leather-soled heel, or a new pair of plastic-soled shoes.
  7. Grass. It’s pretty obvious that any stiletto-loving woman loathes grass when she’s in full glam mode. Who wants to tippy-toe through an entire outdoor wedding? Ew, and there’s nothing more unsightly than a woman who forgets to clean the crud off her heels from the last time she had to hoof it over a grassy knoll because of her man’s poor parking plan.


  1. Boston is notorious for its cobblestones and uneven brick walkways. Going out here is treacherous. You’re bound to see at least one girl fall flat on her face if you’re out in Faneuil Hall on a Saturday night. Which is exactly why I’ve built up a nice collection of wedges!

    1. I hear you Marissa. I never wore flats to anywhere but yoga until i moved to Sydney. Talk about lethal landscaping. A trek to my favorite shopping haunt at Bondi Junction required walking over lumpy, cracked sidewalks, walking up/down a gazillion stairs, taking multiple escalators, and more. I’d walk to and from the train station in ballet flats, then throw my heels on in the mall.

      Yes, I’m that vain. Or that in love with my heels.

  2. Here in Chicago, the worst thing are the subway grates. Wearing flats, you aren’t even aware of them. But slip on some stilettos and you’re gingerly hopping over these grates, with slots just big enough to scrap an entire heel of it’s material, color, pattern, etc. I’ve ruined so many pumps this way. And the damn grates are EVERYWHERE. It’s almost enough to make this Chicagoan pack it in and wear trainers.


    But not quite:)

    1. Ugh. I feel your pain sugar, I do! How many times I’ve tiptoed in Sydney because of those grates…

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