Here’s What You Need to Do to Break in America’s Favorite Work Boot

How to Break in Leather Red Wing Boots

Here’s What You Need to Do to Break in America’s Favorite Work Boot

The AskMen editorial team thoroughly researches & reviews the best gear, services and staples for life. AskMen may get paid if you click a link in this article and buy a product or service.

A few years back, Ruaridh Nicoll penned a column in “The Guardian” about a two-decades long obsession with Red Wing Boots (he owns 11 pairs of the company’s infamously well-constructed and tough to break-in boots). After buying his first pair, they became the yardstick for every other similar product he owned. (Once you own a Rolex, a lot of watches look like toys — that kind of thing.)

RELATED: Best Wingtip Boots
A year after reading it, as Red Wings grew popular as a defacto celebration of “made in America,” we got our first pair: the 1907s. A heady copper color, a project to break in and beautifully designed, all the same. After a couple wears, we realized we bought them too big (a classic mistake) and sold them — better on someone else’s feet. (Resale on Red Wings, like anything well-made, is exceptional.)
That is part of the boot maker’s charm (and frustration). Red Wings, unlike, say, Helm’s, don’t fit true to size. There’s your shoe size, then your Red Wing Heritage size. If you’ve ever lusted after a pair, either for their longevity or comfort, you need to know yours, along with what the break-in process actually looks like, blisters and all. Here, we connect with people who wear them and the company itself to understand how to break in boots that’ll last you a lifetime.

Breaking in Red Wing Boots

People struggle with the Red Wing boot break-in period. So much so, it’s a well-documented thread, particularly on Reddit. The pain. The agony. So on and so forth. Coupled with their outstanding manufacture of long-lasting boots, the small-town Minnesota-based company (for which the boots are named) seems to lead a double-life as shoe-making masochists. Damn them. 

That a boot brand would deliberately make the brake-in period so brutal, so torturous, is odd. Wearers have gone so far as to have developed trusted break-in strategies. Notes about sizing up or down. Their advice reads like a mea-culpa for shilling out $300 for a pair of shoes that ultimately hurt your feet. 

Red Wing is the “heritage” brand that’s become synonymous with quality, longevity and classicism. If you’re already into the daily wear, you’ve likely crossed-over to the owners who wait greedily for temperatures to drop to admire their handsomeness. Now it’s time to preserve that aesthetic. That tobacco-colored hue that’s so intoxicating. Beyond the break-in, here are a couple sure-fire ways to keep them looking fresh as the season turns time and time again.

Find Your Red Wing Boot Size and Style

We visited the Red Wing Heritage brand store off Newburgh St. in London’s Soho neighborhood. It’s dimly lit and woody, a modern day saloon with boots instead of bourbon. The owner wears heritage worker chinos, a vest and a well-loved pair of Iron Rangers — one of the brand’s signature boots, notoriously difficult to break-in (wearing them new is like subjecting your feet to time in a Gulag). Inside, talk is of boots and only boots. Customers come and go over 45 minutes. Most have no problem spending hundreds of dollars on shoes, as easily as if they were buying a cup of coffee.


As part of the fitting process, we try on two pairs of the 877s — the brand’s signature 8-inch boot, and perhaps the one for which they are most famous. Normally, we take a size US 11. Religiously, actually. Not so for Red Wings. In the Moc toe style (Red Wing offered to have us test these for the purposes of writing this article), we try a 10 and 10.5. This is an important decision about fit. How tight is too tight? And how painful do you want that break-in process to be? Get your feet measured up before going further.
People who’ve worn Red Wings for years, credible people, will say, “get your Red Wings as tight as you can stand out of the box.” In our opinion and the opinion of one of the shopkeepers at Red Wing, this isn’t always true. Never leave the store with a size that hurts your feet, to the point that you’re unable to wiggle your toes. (Also, keep in mind the fit on each of Red Wings boots is different; just because you downsize 0.5 on a “moc toe,” doesn’t mean that’ll apply across the board on all styles). Sure, the leather gives, but don’t bank on that happening to the point of a comfortable fit. The blisters (and damage to your feet) aren’t worth it, no matter how good looking they are on foot.
“My number one recommendation,” says Andrew Brodrick, co-founder of Freenote Cloth, whose company often collaborates on product with Red Wing Heritage, “is always try on before you buy.” In an email to us about the boots, which are featured in all of the company’s marketing, he talks about the conscientiousness of Red Wings: how they exemplify a passion for minimalism. And how each person who works at Freenote wears Red Wings every day.
“I prefer to have my Red Wings just a tad small to allow the leather to mold properly to my feet. It’s tough for the first week when a little small, but better for the lifetime. Also (and this is important) big boots can look like clown shoes, so yeah, another reason to go a little small,” he adds. Ideally, with a purpose-built boot, it’ll feel a bit narrow to start, but never so narrow or tight that wearing them leaves you in pain.

Breaking Them In: A Step-by-Step Guide

Satchel B. Moore is Red Wing’s Community Manager based out of Minneapolis–Saint Paul. He has spent a long time thinking about, researching and engaging with people who love Red Wing boots. He explains that all of the company’s boots take some time breaking in, though some, like ours, are easier than others on account of their leather. Beckmans and Iron Rangers, as mentioned, will take a little more patience. Here are his step-by-step instructions on breaking in your first (or newest) pair.

  1. “Pick a style you love, want to wear and that meets your needs. This is most important when it comes to soles, (A Nitrile Cork sole does amazingly well on concrete or indoor surfaces while the Lug Sole is best for outdoor applications). The same is true of the leather: muleskinner requiring less care than a smooth-finished leather to maintain its initial appearance.”
  2. “Make sure they fit. No slipping. Tie them tight to keep your heel down. Again, snug and slightly narrow is ideal. They will stretch widthwise. Never buy a boot that is too short.”
  3.  “Wear them inside a bunch to REALLY make sure they fit [this tip worked wonders for us]. No one wants to buy a pair of boots someone wore to work one day only to decide they were the wrong size. Do this for your own peace of mind.”
  4. Wait for it … “Wear them. Thick socks help with sore feet,” he says.
  5. After about 100 wears, if they get very wet, very dirty or you feel like it: wipe them clean with a wet rag. Apply your favorite Red Wing Leather Care (plain old Mink oil works just the same) product. Let it set. Wipe off. Polish if you wish. Your boots are pretty tough and that leather is amazing, but they aren’t invincible.”

An Obsession: Real and Worth Taking Care of

When Armstrong Naturals’ David Armstrong moved to New York, he was bootstrapped. Without shoes to walk cross-town and go to meetings, he settled on a pair of second-hand Iron Rangers to meet both needs simultaneously — boots he started wearing to construction sites, in mild winters, in his furniture workshop and out to bars for beers afterwards. He was frustrated with having to change boots from one occasion to the next. In his Iron Rangers, he had found the quiver and arrow he was looking for to handle everything. 

Come winter, he was still wearing them, and as the weather turned to sleet, snow and ice, he wanted to make sure his modest investment made it through the desultory New York winter. No longer able to get his hands on a previously-trusted UK-made leather emollient, he started tinkering with solutions to rub on his boots and preserve them, following the ad-hoc advice of a shoe cobbler friend. They were fancy boots in his esteem; he was proud of them and wanted them to last. 

“At the time, there weren’t many options of an all-natural shoe oil, particularly for Red Wings,” he explains about how he started Armstrong Naturals — a small, Brooklyn-based maker of petro-chemical free boot care products. After a little bit of ingredient research, he concluded most commercial shoe polishes were mass-manufactured with parabens, phthalates and petroleum derivatives (mineral spirits, stoddard solvent, white spirit and mineral oil) — disgusting stuff you shouldn’t be rubbing on expensive boots (or breathing in, period).   

In the time since, he’s grown a small hand-made oils and salves business, and has since fallen victim to a minor Red Wing interest which more than six-thousand Red Wing shoe Reddit community members ascribe and contribute to regularly.

“I recently got my first pair of IRs, and they are sand mohave leather which I believe is nubuck? Just unfamiliar with the type of leather and was hoping for some advice on caring for them!,” writes esmith28 on the Reddit thread. 

“Reconditioned my 1-year-old 8085s-happy Red Wing Wednesday!,” writes KaptainKlipa, elated with the ability to prolong the life of his beloved boots (insert badge of honor here).

Whether it’s the 877s you own and want to protect, Iron Rangers you’re hoping to soften, or a pair of weekend-ready chukkas you’re looking to spruce, several simple (some would say obvious?) shoe care commandments will give your boots the extra life they deserve. 

Keeping Your Great Boots Great

People who’ve worn Red Wings for years say, “get your Red Wings as tight as you can stand out of the box.” In our opinion and the opinion of one of the shopkeepers at the Red Wing brand store in Central London where we visited recently, this isn’t always true. 

While guidance varies, never leave the store with a size that hurts your feet, to the point that you’re unable to wiggle your toes. (Also, keep in mind the fit on each of Red Wings boots is different; just because you downsize 0.5 on a “moc toe,” doesn’t mean that’ll apply across the board on 877s and other styles). Sure, the leather gives, but don’t bank on that happening to the point of a comfortable fit. The blisters (and damage to your feet) aren’t worth it.

And now, the care part. Here are a few simple tips:

  • Read your local paper. As for the unexpected weather event, always keep a short stack of newsprint in your closet for when you soak Red Wings through. Stuffing the paper inside and leaving them overnight absorbs moisture like water in sand. By morning your boots will have held their shape and most of the water will be gone. 
  • Rest your Red Wings. Your boots are both work and show-horses, but never wear your boots on consecutive days — another moisture issue. “Wearing boots on consecutive days doesn’t leave time for the inner lining to completely dry-out,” says Armstrong, a habit that will quicken a boot’s natural lifecycle and probably the second biggest reason men’s boots wear-out.  
  • Lube up with love. Too dry isn’t good, either. When leather looks cracked and dry, this is when a good dose of mink-oil, boot wax or a similar product is needed to restore both the colour and the natural suppleness of the outer. A good conditioning three times annually is usually enough to make sure it looks and feels as it should.
  • Brush up on care. Invest in horse-hair bristle brushes and keep the leather clean — while horse-hair might be regularly associated with dress shoes (tought, tight leather and leather soles), it is remarkably effective at removing grit and grime that over time, will wear and crack boot leather. Give them a brush going in the same direction down regularly.

Our Opinion

Leave a Reply

Your email address will not be published. Required fields are marked *