How To Break In Red Wing Boots

You have bought a pair of Red Wing boots and your feet are not thanking you. It feels like you’ve strapped on a pair of concrete boots and two wise-guys named Joey The Clown and Carmine The Snake are going to introduce you to the fishes in New York Harbor

The Red Wing range of Heritage and Workboots is built to last years of hard wear and ensure protection for your feet. Red Wing Boots are made with premium quality materials that will require some time to soften and mold themselves to your specific foot shape, your gait, and the pattern of your sole imprint.

That is all very well, but after the first couple of hours, your feet still feel like they’ve been encased in angry pythons. Will the agony ever end? Of course. And this is how.

Breaking In Your Red Wings In 4 Easy Steps, From Start to Finish.

A good pair of Red Wing boots are on the wish list of many men in the world. Whether for workwear or leisurewear. These boots are built tough and as such can take time to become agreeable.

Red Wing Heritage Men's Iron Ranger Work Boot, Copper Rough and Tough, 9 D US

Red Wing Heritage Iron Ranger Work Boots
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New leather straight out of the box will always be stiff and inflexible but here are the steps to ensure a long and comfortable relationship with your new Red Wings.

Step One (Buy The Correct Size)

The first step is always buying the correct sized shoe for your foot. A good tip is to try on shoes after 3 pm. Your feet swell during the day, sometimes as much as half a size. However, footwear manufacturers do tend to size their offerings differently which sometimes makes this a bit of a hit-and-miss exercise.

Red Wing Heritage Men's Classic 1907 6-Inch Moc Toe Boot,Copper Rough & Tough,10.5 D US

Red Wing Classic 1907 Moc Toe Boots
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This is what a Red Wing employee has recommended to us:

They do run around a half to full size larger than most shoes, but there are ways to check for a good fit. You want your big toe just behind the toe of the boot, and you want to feel a small amount of pressure against the sides of your foot -- nothing uncomfortable, but you want to feel it”.

Do not fall for the advice that you should buy a pair of boots a half-size smaller so that when they wear in they will stretch out to fit your foot. While this advice may be true for some other manufacturers who use inferior leather. It is not the case with Red Wing.

Step Two  (Wear them at home)

The second step is to wear them at home for an hour or two at a time for a week or so. Your new Red Wings are going to be a little painful to wear in the beginning no matter what you do but at least you can take them off if they become so when you’re at home.

Red Wing Heritage Men's Six-Inch Moc Toe Lug Boot,Brown,7.5 D US

Red Wing Heritage 6-inch Moc Toe Lug Boots
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The added advantage to wearing them at home is that you can admire them in their pristine state for just that while longer. Enjoy it; they are never going to be this clean and unscuffed ever again.

Step Three (Wear with your thickest socks)

While you are stomping around the house in your new boots try to wear the thickest socks you own. Two pairs if you can manage it. Wearing thick socks will provide gentle pressure on the leather.

Just like your own skin leather prefers a gradual expansion if you are to prevent stretch marks and weakness at the seams.

A bonus to wearing thick socks is that you will greatly reduce the possibility of blisters and hot spots on your feet. If blisters do develop, slap on a Band-Aid to prevent infection and to provide even more comfort to the painful area.

Step Four  (Condition the leather)

The fourth step is all about conditioning the leather. Leather is just another type of skin. It needs to be moisturized occasionally. Moisturizing will extend the life of your Red Wings, especially if you live in a rough climate with rain, snow, and salt on the roads.


Red Wing Weekender Canvas Moc Toe Boots
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While you do not have to apply conditioner to your boots after every use, Red Wing recommends conditioning after 100 wears or so. Leather conditioners will extend the life of your boots and they help soften the leather, making the break-in period a bit easier on your feet.

What You Should NOT Do When Breaking In Your Red Wings

The internet is full of bogus tips on breaking in new shoes and boots. Here is a list of things NOT to do:

Do NOT dunk your boots in a tub of water.

Your Red Wings are designed to be worn out in any conditions and they will shrug off almost any abuse. However, immersing your boots in a tub of water for an extended period in an effort to soften the leather (which will actually happen) will have the reverse effect of your good intentions by actually shrinking and warping the leather and even the soles of the boot.

Red Wing Mens Classic Chelsea Leather Ebony Boots 10.5 US

Red Wing Classic Chelsea Ebony Boots
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Do NOT blast your new boots with a hairdryer.

Sure, the heat will make the leather more pliable but prolonged exposure to heat will make the leather dry out and crack.

Do NOT wear wet socks to try to soften them from the inside.

Doing this will certainly soften the leather but it will also guarantee painful blisters which will only prolong the break-in period. Moreover, who in their right minds wants a blister on their foot?

Do NOT go without socks either.

Certainly, this will introduce a more exact copy of the dimensions of your foot to the inside leather of your Red Wing, but it will also strain your feet and will not speed up the process.

So What Do Red Wing Themselves Say?

Red Wings take time to break in. They provide outstanding quality, but there’s no promise that the boots will be your best friend after two days. It’s a relationship that has to grow. Don’t try to do too much too soon; you should not walk around for eight hours in a brand new pair of Red Wings. Try wearing them at home, let your feet get used to them slowly. A good sock will provide protection from the new stiff leather. It will also provide some cushioning for the foot.

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Feature Image Attribution

Myotus, CC BY-SA 4.0 <>, via Wikimedia Commons

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