If you’re lucky, you probably don’t have to go shopping for tall boots all that often. Even if you have the worst luck with broken zippers, you probably buy tall boots less frequently than you buy bell boots. My last pair lasted me a good three or four years, and I discovered that the process has changed a lot since the last time I went shopping.

I made this step-by-step guide so that others, while they may suffer, will at least know what’s coming to them. (Note: I do not drink; if you do, feel free to sub in a glass of wine at every mention of cookies.)

Step 1: Reluctantly reach the conclusion that the heel on one of your boots is probably beginning to dry rot. Ignore this for a while, until the detaching part of the heel separates so far from the leather that you can no longer get a spur strap around it. Continue to ignore it, until your Sassy Mare calls you out on the spur not being in place by ignoring all requests for a canter transition. When she asks if that’s a fly on her ribcage, decide it’s probably time to buy new boots.

Exhibit A: Once the heel is fully detached from the boot itself, and past a cobbler’s help, the boot-buying experience can be delayed no longer. Photo Courtesy Of Joe Nevills

Step 2: Pull up the website for the company you bought your current boots from for about $250. Think how grateful you are that, years ago, you discovered a company selling wide-calf boots that don’t remind you of wearing corsets on your legs.

Realize they no longer sell boots in this price range. Discover you can spend $500 on something that sounds like a foreign sports car or you can spend $180 on boots that the product peanut gallery suggests may be made of cardboard.

Step 3: Begin Googling haughtily, muttering about how you’ve never spent a month’s board on boots, and you’re not going to start now.

Step 4: Return to the original website. Come to grips with spending $500 on boots, but resolve that if you’re going to do that, you’re going to get a height that doesn’t poke you in the back of the knees like a reverse reflex test.

Step 5: Wander the house looking for a tape measure to measure your legs. Trip over cat and stub baby toe. Ponder whether you will end up buying custom boots to account for toe loss. Laugh at the notion of buying custom boots as an adult amateur who barely shows anymore.

Step 6: Measure legs. Measure legs again. Google “How to measure legs for tall boots.” Determine that, according to Boot Company A, your legs are both “wide” and “short.” Limp into kitchen and grab package of Oreos.

Step 7: Stare at legs in mirror, munching on Oreos. Ask husband accusingly, “Why have you never told me my legs are short and stubby??” in between mouthfuls of Oreo. Question whether he’s looking at you strangely because you’re spewing cookie crumbs or because he can’t believe you don’t already know this about yourself. Decide he just can’t bring himself to tell you your legs are like sausages—short, stubby sausages.

Step 8: Throw out shorts.

Step 9: Grab another Oreo and decide that, fine, you’ll buy “short,” “wide” boots for $500 if they just fit nicely. Discover Boot Company A does not make boots in both “short” and “wide.” Contact customer service to see if this is a mistake. Learn from a polite, tactful rep that they so rarely sell this combination of size requirements (which you suspect they privately have some unfortunate nickname for, like “Garden Gnome Boots”) that they’ve decided to stop stocking them.

Grab another Oreo. After much venting and crumb-spewing to the husband, who has been nervously watching your interaction with Boot Company A, pass out on couch in a sugar-induced coma.

Step 9: Armed with the perspective of a night’s sleep, resolve to make a trip to the nearest consignment tack shop to try on boots thinking you surely will be a “regular” in some brand, somewhere.

Step 10: Discover how difficult it is to zip up consignment boots with their zippers tied together whilst wearing both a baseball cap and face mask. Think vaguely about the yoga classes you bailed on as you try to stand on one foot while bending down to use both hands to yank on one zipper at a time, trailing the other boot across the floor like a can tied to a bridal tailgate. Flail around the tack shop basement, bumping into used dressage saddles until you accidentally shift your face mask over your nose and into your eyes, causing you to run headfirst into the boot rack. Wonder whether the signs about video surveillance are security theater or if someone actually is watching this performance.

Step 11: Despite becoming winded trying to zip up the first pair of boots unsuccessfully, decide you simply will try another pair. Feel encouraged about the ease of zipper up the back of your ankle until it stalls at the back of your calf.

Step 12: Repeat the process with 10 more pairs of boots, including a few pairs marked “custom” that you hoped were created for people like you, who couldn’t find boots created for normal humans. Dejected, leave the tack shop and return home.

Step 13: Grab an Oreo and your laptop, thinking that someone on Facebook Marketplace must also have Garden Gnome calves and will be interested in selling their boots. Spend a cumulative five hours over several weeks searching every sale post you can find.

Step 14: Wonder if all the “tall,” “slim”-legged people out there realize how easy they have it. Roll your eyes as you read online complaints about how difficult it is to find a particular style of boot in both “tall” and “slim.” Refrain from DM’ing them to ask what life is like on the runway. Measure legs again. Grab another Oreo.

Step 15: Discover dry-rotted heel has fallen off boot completely now, creating an unfortunate witch’s hobble when you walk around the barn. It’s fine, you tell people. I’m still searching for the right pair.

Step 16: Order slightly more expensive pair of Garden Gnome boots from Boot Company B. Since you’re already out of pocket on this, decide you’ll get something really fun and order a brown pair.

Step 17: Squeal with delight when the new boots arrive, forcing yourself to forget that they cost twice what you’d planned to pay.

Step 18: Discover that boots will only zip up halfway. Check size. Grab an Oreo. Stomp around house in half-zipped boots which do not flex at the ankle, scaring cat. Insist that walking up and down stairs sideways is “actually great cross training!”

Step 19: Call Boot Company B to inquire whether there has been a mistake. Just break them in, you’re advised. It takes a day or two.

Step 20: Wear boots in house for one week. Discover you can zip them as long as you wear shorts (recovered from dustbin) and no socks. Eye drawer of perfectly serviceable breeches, wondering if anyone makes breeches from thinner fabric. Grab another Oreo.

Step 21: Briefly research just how outrageously priced are custom boots, anyway?

Step 22: Very outrageous. Never mind. Fail to mention this to husband. Just in case.

Step 23: Replenish Oreo supply.

Step 24: Call Boot Company B again while icing blisters. Learn that “Many people just wear them in a hot shower” and contemplate how the only thing worse than having really hot leather on your legs is squishing around barefoot in wet shoes all day.

Step 25: Purchase boot-stretcher spray. Whimper with relief when it arrives in the mail.  Eagerly spray as directed along the insides of the boots. Learn from instructions that you should now put the boots on and wear them for a while. Discover—as all the stretcher spray runs down and settles on your bare feet—that, in fact, the only thing worse than wearing knee-high boots soaked in hot water is knee-high boots soaked in cold foam.

Spend next week trying to rid basement of pungent boot-stretcher fumes, which unsettle the cat. Open a new package of Oreos, because what do you have to lose now?

Step 26: Repeat approximately five times, gradually introducing socks into the equation. After two weeks, find you can wear breeches, thereby ending your fashion foray into “tall boots with athletic shorts,” which the neighbors found so delightful.

Step 27: Congratulations! You can now ride in your new tall boots. The blisters will stop in about a month.

Postscript…

Step 28: After two months, buy new horse and, after a particularly exciting lesson, decide you will aim for a few dressage schooling shows this season. Realize your boots are brown. Grab a fresh pack of Oreos on the way home. You’re gonna need ‘em.