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Vintage Riding Boots

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. I’m not 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. :)

11 comments to Vintage Riding Boots

  • abs

    just fyi- in case you are ever in need of another pair of riding boots- you could have paid about $10 more and gotten a similar pair- brand new from dover saddlery- i don’t know if you ever rode dressage- but they really have nice selection.
    http://equestrian.doversaddlery.com/search?p=Q&lbc=doversaddlery&uid=520834720&ts=catnav&ref=wintersale&w=*&af=catsub:ridingboots%20cat:ridingapparel&isort=globalpop&method=and&view=grid&cnt=300

  • Here’s your problem: legit riding boots are made for RIDING! Not walking except for just a bit between the stalls and the arena, etc. They will always kill yer feets if you walk alot in them!
    You need some Frye boots! They wear like iron and once broken in, are comfy. I’m sure you could find some on Etsy or eBay…
    P.S. love your blog, can’t wait to see what this big project is you’re working on!
    Cheers
    Dina

  • I love the black boots with the laces!!! I recently purchased some brown riding boots on ebay, they fit great but I have the same problem with the ouchies. The thick piece of leather that goes down the back of the boot basically cuts into the back of my foot.

    I actually gave in and bought (via a birthday gift) some expensive (for me) ASH (fake) riding boots on bluefly because I wanted something classic and comfy. Now I just need to decide what to do with my first pair. I guess I can try the moleskin method because they are darker than the new ones, so it would be nice to keep them.

    Do you notice that they are slippery on the soles? I have a problem with almost falling all the time due to the little metal nails on the sole. Maybe they are a hazard to my health and its best to sell them……IDK???

  • I once had a pair of black riding boots from Enzo Angiolini, and they lasted for years. Why I parted with them, I do not know. They were so versatile, and fit like a glove. Have I ever seen a pair since that has not cost at least $350 for the same look? No! My Enzo boots were perfect for late night adventures and long walks alike. I miss them!

  • Sage

    OMG!
    Ok THAT is about the cutest thing I’ve ever read…on BOTH ends of the story..MY how we learn from our own children…it NEVER ends!
    now…if I could just learn to play the guitar….
    just sign me..another proud mom
    sage

  • Krishji

    THE cutest story ever! Your mom rocks my world. I also live my life in tall flat black boots – knee-high Dr. Martin’s with the Soles Bouncing! Those shoes last for five years or more. You may need to have the zipper replaced sometimes, but that’s not too pricey.

  • A Rider

    I read this hoping your post would contain a brand. Just like in the fashion world, riding boots get expensive, and in my experience the more expensive ones break in faster and are far more comfortable. If you bought a pair of crappy ones I can only cringe at what your feet may be feeling! Riding boots are (I agree with a previous comment) for riding! I would never even think of wearing mine as fashion even if when pressed for time I’ve worn them to class. Like in fashion though, trust me, you know what brands will kill you.
    This was a super cute post though!

  • My next trunk show is March 23rd at 6pm in Union square – I hope you can come by! after that I will have a little booth at the Artists and fleas market off bedford ave – exclusively vintage there and same great prices. :)

  • LW

    cute story. the apple doesn’t fall far from the tree.

    i sprung for full priced authentic Ariat cowgirl boots at a “real” western store last spring. they were stiff as boards but after selectively wearing them an hour here or there, i can honestly say i’ve broken them in . real leather will mold to your foot….. eventually. btw, i rock these investment boots with my thrift wear wardrobe…..

    your blog is awesome and it’s funny. thanks!
    thx.

  • Priscilla

    Miss your updates. Hope you are well.

  • mtb

    i broke the code on breaking my riding boots in. Obernauf’s Heavy Duty L.P leather preservative. I got a dollar sample size at a cowboy boot and supply store (about the size of a bare minerals foundation container). I will never run out, it goes pretty far.
    I heated my boot up with my blow dryer, rubbed the (beeswax) LP into the leather on both the inside AND the outside, stuffed the heck out of them with wet wadded up newspaper and stuck them about a foot in front of a space heater for 15 mins, then left them to dry on their own for a day.
    When dry one fit great the other was snug so i rubbed them both inside and out, put them on with wool socks for about 20 mins, repeated this the next day and now i hate to take my boots off.
    A good leather protector will soften the leather. One note…my Frye boots (i totally agree with the above poster) were a absofraginlutely beautiful shade of an umberish olive colour before the protectant. Now they’re a deeper shade but they feel great!
    You might try a google search for rubber dressage boots for rainy mucky days on the subway. They look like leather but are great for snow, rain, salt, etc.
    Love your mum!

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