/ Giveaway /

September is the time of the year when the world of denim and heritage comes alive again. We’ve nothing against the Aloha shirts, shorts, iced coffee, and Vitamin D of spring/summer, but this transitional month allows us to get excited about wearing more denim, work shirts, flannels, outerwear, and all that good stuff.

If you need help getting in the mood, we’ve partnered with KATO, Carl Murawski, Valet Mag, Blazer, Inside Hook,Fabricateurialist, Denimhunters, and Cool Material to give away a KATO prize pack. Worth over $900, this prize is chock full of autumnal goodness, consisting of:

• One pair of Raw Selvedge Denim Jeans(Winner’s choice of fit)

• The Ripper Triple Twisted Plaid Shirt – Solstice

• The Blade Jacket in Copper Raw Selvedge Denim

That’s a whole outfit ready to tackle fall/winter for many years to come. To enter the giveaway, all you have to do is drop your email on this page before 29 September 2025. The one lucky winner will be notified by email and have 24 hours to confirm their shipping and size information. All entrants will be signed up for all partners’ newsletters, from which you can unsubscribe at any time.

The Do’s and Dont’s of Breaking In a New Pair of Leather Boots

The Heddels team provides tips on what to do and what not to when breaking in a new pair of leather boots.

Albert Muzquiz

I’m sure there are plenty of you who are already rolling your eyes as you click your way to this article. The eye-rollers have probably got their boot break-in figured out already, but for every skeptic, there are many more fresh feet who may be seduced by some of the less prudent break-in methods advertised online.

In this article, we will go through some fundamental do’s and don’ts for breaking in a new pair of leather boots.

About the Break In Process

The thing about new boots, as with new jeans, is that they will take some work. Pure and simple. And while there are a handful of minor shortcuts, it’s really all about getting a tough piece of hide to slowly conform to your feet.

We live in an era of instant gratification, where we can get just about anything we want at any time. Pair this with a society long steeped in fast fashion and the fact that most folks wear comfy, padded sneakers, we’re simply not used to a product that requires blood, sweat, and tears to make perfect. The journey of breaking in a pair of boots is a deeply personal one, but it doesn’t have to be all that difficult.

How to Break in Your Boots Right

DO Buy High Quality

If you’re going through the tribulations of breaking in a pair of leather boots, you want your efforts to be worth it. The whole joy of breaking through those first few weeks is that the pair on your feet will be much more valuable to you than anything new off the shelf, so try to make sure you have a quality pair to start. Look for something that has Goodyear welted or stitchdown construction, as these are two shoemaking methods that make boots easy to re-sole in the future, long after you’ve broken them in.

Our entry-level pick is the Red Wing Iron Ranger, which has a modest break-in period, a full-grain and oil-tanned leather upper, and a Goodyear welted recraftable sole, so a pair that, if treated right, can last decades. You can read more about why we picked it in our full cutdown review here, or if you’d like to check out other options for what the wide world of boots has to offer, see our guide to the Three Tiers of Welted Footwear.

Makers of Quality Leather Boots Include:

• Red Wing Heritage

• White’s Boots

• Russell Moccasin

• Thorogood

• Viberg

• Meermin

• Alden

• John Lofgren

• Grant Stone

• Easymoc

• Oak Street Bootmakers

• Unmarked

• Lennertson

• Hanker Boots

• Drew’s Boots

• Nicks Boots

• Bordon

• Chisos

• Dievier

• Warfield & Grand

• Parkhurst

• Cordobes Boots

• Caswell Boot Co.

• Brandle

• Helm

• Jim Green

DO Get The Right Fit

The most important piece to breaking in a pair of new leather boots comes before you’ve even purchased them. It’s imperative that you get the sizing absolutely correct before you begin the break-in process. When you get a new boot on your foot, it should feel stiff, snug, but still good. If a shoe feels like a leather foot prison, don’t kid yourself—that won’t change.

When making a major investment like a pair of leather boots, it’s always best to make the purchase in person. I know that it’s hard to wait, but it’s always better to cool your heels and wait until you can see it’s actually going to work for you. If in-person shopping isn’t possible for you, order a couple of sizes of the boots you’re interested in, and return the sizes that don’t work for you. A lot of advice has to do with stretching boots that are too tight. You can avoid most, if not all, that nonsense by nipping this issue in the bud with correct sizing.

Everyone’s feet are different, so lock down a size and last that works for your foot, and you should be good to begin breaking them in earnest.

DO Wear Them Around The House

Depending on your pain tolerance, you may not want to just start wearing your crunchy new boots out and about. You also may not like the way they start out, all new and shiny. A great course of action is to start wearing your boots around the house in small doses. The boots will hurt for a couple of days, no matter what, but if you space out that wear time over a longer period and in the comfort of your own home, it won’t be so bad.

You should try to enjoy this period, even though you may be uncomfortable. Your boots will never be this clean and pristine again! Memorize the way they look, so you can treasure every scuff and crease you gain over the next couple of years. You’re in for a treat. Or, you can document your journey and send them over to us for a Fade Friday feature.

DO Get Comfortable, Thick Socks

This may not be an issue for our northern and cold-weather-savvy readers, but for those of you breaking in new boots in milder climates, you’re gonna need new socks. Sure, after you’ve had your leather shoes or boots for a while, you can wear any old Hanes sock with ’em, but when they’re as stiff as the box they came in, you’re going to need a little extra protection.

Camel City Mill Heavyweight Wool Boot Socks, available for $29 from Camel City Mill.

The early days of breaking in a pair of boots aren’t just about creasing and softening the upper; it’s also about getting the midsole to conform to your unique arch. Basically, at this early stage, your foot is being assailed from above and below, so a little extra cushioning can’t hurt. Heavy cotton socks or a light Smartwool are both good options, but there’s no perfect answer. Whatever feels best within your budget is all you need. And, thicker socks can even help stretch the leather more, speeding up the break-in process.

What NOT to DO

DON’T Submerge Your Boots in Water

This is a common break-in tip you’re likely to see, but one that we do not endorse. There are plenty of variations on this theory, either to fully submerge the boots, partially soak them, or even wear them around for a day with wet socks. The issue is that, though leather can stand a certain degree of moisture, it’s ultimately not great for your boots. Though it sounds counterintuitive, water can actually dry out your leather boots, eventually leading to greater problems like cracks and tears.

Some could argue that the leather is soaked with water during the manufacturing process, so it can’t be bad. But that’s done in a very contained environment by people who know what they’re doing. If you feel passionate about soaking your new $300+ boots in water after you buy them, by all means, go ahead. We’re just here to let you know that we don’t approve.

DON’T Heat Em Up

It’s perhaps beginning to register that some of the more extreme break-in techniques are questionable at best. This is true of the heat ’em up genre of break-in hacks. People have suggested putting them in the oven, steaming them, and even blow-drying them, but the fact of the matter is…just don’t.

While heat could feasibly soften leather, it also dries it out, which is the only thing you shouldn’t do to leather. That’s why leather conditioners are so important. While theoretically, careful heating could soften parts of the boot, the long-term effects are potentially far worse. You really shouldn’t have a boot that fits you so badly that you’re resorting to such drastic measures anyway.

DON’T Wear Them Every Single Day

We know, once you and your boots have made that special break-in bond, you may never want to part with them. But the love that burns brightest burns fastest, and your leather footwear friends really need some alone time.

Your feet sweat, some more than others, and the leather in your boots absorbs a lot of that moisture and needs time to dry out in between wears. If you don’t give them sufficient time to recover, everything about them will begin to degrade faster and maybe even start to mildew.

A good rule of thumb is to give at least one rest day every 2-3 wears to ensure long-term health.

Conclusion

New boots are almost exactly like raw denim. You can sweat the initial discomfort and try to cut corners, but the fact of the matter is that you’ll be wearing these things for a long time before they start to look like those inspirationally beat-up pairs you see on Instagram. Though we’re eager to get to our destination, try to enjoy the journey. You spent a ton of money to buy a pair of boots from one of the world’s top manufacturers, so don’t baby them while you wear them, and ironically, don’t destroy them while they’re off your feet with cockamamie schemes.

Do your due diligence and find a boot made from a leather that’s right for you. A slow-aging rich cordovan, a nuanced roughout, or maybe a quick-to-patina veg-tan. When that’s done, make sure the boot feels good on your feet and you’re all set. We sincerely hope you enjoy your journey and that you didn’t roll your eyes too much.

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