At some point between my college years and today, vintage clothes to me became used clothes, and I went from loving them to very not loving them. Maybe it’s that gradual process of discovery that college ideas may not be the best ideas (Jager shots! And pizza! For breakfast!) mixed with a desire to, when living in a city where there seems to be a lot of urine in traditionally urine-free areas, keep as clean and germ-free and “mine is the only skin that has been in this shirt” as possible. Hard to say. I’ve ebbed and flowed with it over the years—there are more than a few vintage Hawaiian shirts in my closet—but lately I’ve been a store-bought kinda’ guy.

And as someone with this point of view, you’d think that were I to have a change of heart, it wouldn’t be a change of foot. I mean, used shoes…where another person’s feet have been…maybe when not in a sock? Oh, the humanity! But alas, that’s exactly the evolution my position has taken. And it was all in the name of love, the love that can only exist between a man…a man and pair of boots.

I’ve written here a couple of times about my checkered past with Red Wing Iron Rangers. To me, they have been both Holy Grail and my own version of Steve Martin’s “cruel shoes”, togs I lusted after but made my feet hurt as though they’d been laced-on by black ops at the GitMo shoe store. Were there a film to be made about me and Iron Rangers, it could surely be titled, There Will Be Blood.

I’ve tried twice to break in a pair of 10 ½ D’s in classic amber harness leather, and almost made it. Almost. But I have a high arch and a low threshold for pain, so it was not to be. I know I’m not alone—successful Red Wing break-in stories are like those of prison break-outs—when you make it, a legend is born.

So I got to thinking—I knew my size and felt confident that life-long comfort could be mine if I could just make it past the breakwater—like Tom Hanks in Castaway, I’d be all free and happily rescued by a passing freighter! So to speak. So why not have someone else break them in for me? Could I do that…pay someone to wear my new boots until they got comfy? That seemed like a weird end to pursue (and that’s coming from me, a weirdness connoisseur), so I took the path less weird–I bought me a pair of well-worn, straight-up USED Iron Rangers from a stranger, their stiff, aching newness a thing of someone else’s (and their podiatrist’s) memory, not mine.

Come to find out, the used boot market is hoppin’, and I had to wait a number of months for a pair to come along with the right size, price, and condition (used, not used up). What follows is what I did to get my “vintage,” unabashedly worn Red Wing Iron Rangers back in my version of perfect condition. I’m now a used shoe advocate…damn near an evangelist. With a little patience, a few simple tools and a couple hours of elbow grease, you can bring any good boot or shoe back to life while saving yourself that awkward-to excruciatingly-painful getting to know you phase. And a few bucks, too.

Step 1: Start With The Right Stuff

If you were going to restore a car, would you be better off investing in a ’59 Cadillac or a ’79 Pinto? Exactly. If a boot or shoe is made of high quality materials, the idea that they can be “restored,” resoled and refurbished is already built into them.

I went with Red Wing Iron Rangers because I know they’re made to exacting standards of premium materials. (Managing Editor David Shuck did an exhaustive review of a number of boots, including the Iron Ranger, and you’d be well served to read it.) Red Wing, Thorogood, Alden…look through our archives for a wealth of candidates, as they’re all good options for boot restoration, as are top notch shoes like Church’s and Allen Edmonds (for an exhaustive list at any price, check our Three Tiers of Welted Footwear).

Basically, make sure you get something worth the time, money and effort. Also, if you wear your heels down on one side or the other, try to find a pair being sold by someone with the same weird walk as you.

I spotted these on eBay and snagged them for $110 shipped (that’s a savings of $100-200 off retail, depending on where you buy ‘em). Yes, they look beat-to-Hell, but I knew there was lot of life left in them and a clean, oiled finish lay just waiting to be revealed beneath all that dirt. (Imagine—somebody bought a pair of work boots and actually worked in them. Freak.)

Lastly, you don’t want to go through all this unless you’re sure they’re going to fit—as much as you can, make sure the size and style are right for you, as all the cleaning won’t help you a lick if they don’t fit.

Step 2: Get some Rags, Brushes, Lotions and Potions

Maybe you’ve already got some shoe care stuff under the sink, so you could be ahead of the game. As for me, living mostly in Vans Slip-Ons these days, I was starting from scratch. After watching a lot of Youtube videos on boot restoration (trust me—a lot), I realized that, if I wanted to, I could easily spend as much on fancy leather creams and goos and exotic-hair’d brushes as I did on the boots themselves.

If that’s your thing, have at it. But really, all you need are the following, and this $30 investment will see you through a number of pairs of boots and shoes, from full-resto through regular, general maintenance.

I went with horsehair for the brushes (Kiwi), Feibing’s for the saddle soap, and Cadillac for the conditioner, as it leaves more a satin and less a glossy shine as other brands. There are plenty of other very respectable options out there, but keep in mind—nothing will magically transform your boots, that’s why it’s smart to start with good solid candidates in the first place. You’ll need a few rags as well, but I assume you already have those.

Step 3: Roll Up Your Sleeves

For starters, remove the laces and wipe the boots as clean as you can with a rag or wad of paper towels. (I washed the laces in the sink with a little dishwashing liquid. I could have gone with new ones, but I didn’t want the laces to appear newer than the boots. Choose your own adventure.)

Then, following the directions, apply the saddle soap (with a little water) to the applicator brush and thoroughly “wash” the boots, being sure to get in all the seams, creases, nooks and crannies.

Then, with the applicator brush clean but wet, rub off all the dirty suds. Let dry, and then do it again if necessary (these took two spins in this wash cycle). Remember, leather—especially the good stuff—is a natural hide, so harsh soap and water is going to dry it out (like your own skin), and you don’t want that. Saddle soap is formulated to help safely return the leather to a more nourished, pliable state.

Next, and again, following the directions for your specific product, liberally apply some leather conditioner to the boots and let it soak in. This step turns your dry toast boots into buttered toast boots, and the results are pretty amazing.

Feel free to use your toothbrush to get the conditioner into the hard to reach areas of the boots (you were likely due for a new one anyway). You should repeat this step if your boots were extra thirsty and really sucked in the conditioner. Mine were, and I applied two liberal “coats” of the conditioner.

Then, buff with a clean rag and give them a brushing with the shine brush. At this point you could be done (I was)! Re-lace ‘em and get back to work (or as in my case, re-lace ‘em and get back to sitting quietly at the computer, letting the cats get a contact high off the new-boot smell).

Step 4: But Wait, There’s More!

There are leather care products out there that claim to “repair” the leather in your boots and shoes, essentially “filling in,” like a liquid leather putty, the scuffs, scars and scratches left by years of wear. Saphir makes perhaps the best known, and I have seen it achieve remarkable results. On dress shoes. You really have to decide how “restored” you want your boots to look. Would you want a product that restored the indigo to your denim fades? Likely not—patina is the whole point–so unless you’re restoring a pair a shoes to be worn for “dress” occasions, you likely don’t need or want this step. I didn’t, as I like the scrapes and dents the other guy got for me. (I consider them part of the purchase price–I bought the boots, but mostly his time wearing them, along with the end results.)

And then there’s resoling. My boots don’t need a new sole yet, and I doubt I’ll ever explore that option as these will get only occasional, casual wear. And now that I live in California where I drive everywhere and even Uber it from the couch to the kitchen, I don’t wear out soles the way I did walking the streets of New York. Also, considering that a proper resoling can cost between $50-100, you might want to consider if your used boots are worth that investment, and if you were looking to avoid all the stiffness of a new pair of boots, if you want to break in that new sole yourself.

Step 5: Marvel At The Results!

Ideally, should you tackle a project like this, you start it with reasonable expectations. If you want to take your boots back in time to their fresh-from-the-box condition, you’re going to be disappointed. However, if you’re hoping to give a second chance to a battered pair of boots or shoes, I think you’ll be happy you’ve made the effort.

You may be wondering about the inside of the boots, the place where the other guys feet spent their time. Honestly, I try not to think about it too much. Once you’ve decided to go the used boot route, some things are best left unpondered.

I will say that these were pretty clean upon arrival, and the only sanitizing step I took (as I don’t live near a bowling alley and thus had no access to whatever it is they spray on the shoes between rentals), I wiped them out with a mildly damp and soapy rag, gave them a few sprays of Febreze, and stuffed them with dryer sheets for a week or so. The look and smell no worse than anything I already own.

Most importantly–MISSION ACCOMPLISHED–these boots feel great. Yes, the footbed was molded to someone else’s foot, but that’s not proved a hindrance to them being far more comfortable than I could have dreamed. The instep is nice and flexible as is the ankle area–essentially, they’ve been broken like a wild horse, and I get to take nice gentle rides with no fear of getting thrown. Or blisters.

Sure, some of you will think is is cheating, that you should suffer the break-in period to enjoy the patina and comfort of old boots. My friend Lee likes to say you have to “earn your fades,” and I know he’s waged war with his own Red Wings, and won, but eared a purple heart both times. Like Danny Glover in the Leathal Weapon movies, I’m getting too old for that shit. I’ll do it with denim, but I took the easy way with these boots and dammit I’d do it again. I see a pair of Indy Boots in my future, and they sure as hell ain’t gonna’ be new.