A month or so ago, I popped into Hamlet’s Vintage – purveyor of the offensive $15 beat-up tee – on a mission: I needed tall, black, flat boots. Again.
In the past year alone, I have gone through not one, not two, but THREE PAIRS of tall flat black boots. When I say “gone through” I don’t mean I’ve lost them or damaged them: I’ve simply worn them out.
Maybe today’s footwear isn’t tough enough for the city’s mean streets; maybe I tend to stomp aggressively instead of tread lightly; maybe I have a slight Napoleon complex. Whatever. I was cast as the elephant in a childhood zoo-themed ballet production; it’s not like I’m morphing into some dainty graceful creature anytime soon.
It’s not like I haven’t tried to extend the lifespan of my last three pairs of tall black flat boots. All Dr. Cobbler does is prolong the inevitable: There is no chocolate coated miracle pill for bringing dead shoes back to life. At least, not after I’ve worn them.
When my last pair expired, I vowed to do things differently. THIS TIME, I would purchase boots constructed to withstand destruction; boots that looked at the subway grime and grey clotted snow and toxic puddles and scoffed ‘BRING IT ON.’
So I popped into Hamlet’s Vintage, discovered they were having a sale, zeroed in on a pair of tall flat black riding boots, paid their $110 sale price (not great, not awful) and thought it’d be smooth sailing from there.

The boots have been kicking my ass ever since.
The issue isn’t strength or durability – old school riding boots are built for post-apocalyptic conditions. The problem is that they’re designed to “follow your body’s contours” i.e. suffocate the lower halves of your legs so you look as though you’re one with the horse or whatever.
Well WHAT IF THERE IS NO FUCKING HORSE?
Then you wear them out for an hour and realize your feet are numb and your ankles are blistered because leather of this thickness and stiffness doesn’t even exist anymore and your entire lower legs, from knee to big toe are screaming in shock and protest. Then you go get Toughstrips Band-AIDs and they don’t work, so you try moleskin, except instead of putting it on your feet, you use it to line the interior of the boot for permanent padding. This makes wearing the riding boots bearable, and after three weeks of continuous battle, they finally start to soften and give. Then, and ONLY THEN, can you be pleased with the purchase you made one month ago. This is where I find myself today.
So, how’d my mother beat me at my own game? Check this Sharesies! courtesy of Mom herself:
Dear Cheap JAP,
I couldn’t resist sharing my fabulous good fortune with you.
Found these custom “Made in England” gems at my local shoe repair for $25.00!!!
They’d been sitting there for 3 weeks waiting patiently for their rightful new owner; yet unfortunately, every lady who tried to slip into them was immediately met with the sore disappointment of an unforgiving narrow leg. The couple who own the shoe repair aptly named them the “Cinderella” boot.
And so, in my fifty-first year the heady OOMF I received, when pray-tell they exclaimed, “you’re ‘Cinderella!’” led me straight to the decision to dress up as Betty Draper at the Mad Men Soiree I would attend on Saturday night.
And she lived, happily ever after.
Best Always,
Mother
Too cute. So cute in fact, that I’m almost not bitter at her snagging a pair identical to my $110.00 riding boots for $25.00. Almost.
Just kidding. She got me into riding boots to begin with; I got her into shopping cheap. That makes it a fair trade, methinks.
Way to go, Mom. Thanks for sharing.




















































