How To Break In Red Wing Boots in 4 Easy Steps

Breaking in a pair of Red Wings is sort of like earning a merit badge. Whether you’re 5 or 95, the process helps you appreciate the shoes more, if only because they symbolize that you’ve overcome long odds and earned something new and foreign to your closet. If you are looking to purchase some, this post will tell you all you need to know about how to break in Red Wing boots.

Red Wing’s Heritage and safety boots are built to last, ensuring protection for your feet for many years. They’re crafted with premium quality materials that will soften and mold to your specific foot shape, gait, and sole imprint over time.

But after your first few hours of testing out Red Wing boots, your feet ache as a band of angry pythons attacks them. Only those who’ve experienced the bittersweet agony of this scenario can tell the tale. If you’re currently passing through the pythonic pain of breaking in Red Wings, I’m here to slam some good news on your screen: the pain will end. Here’s how to make that happen.

How to Break in Red Wing Boots Step by step

Red Wing boots have been a favorite of humankind for generations. Whether purchasing them for work or leisure, it’s important to break in your new pair of Red Wings correctly.

New leather will be stiff and inflexible, but proper care and a little patience will help your Red Wings will soften up quickly, ensuring years of comfortable wear.

Step One: Buy the correct size

When choosing shoes, always buy the correct size for your foot. A good tip is to try on shoes late in the day when your feet have swollen slightly. However, different manufacturers tend to size their offerings differently, so it can be hard to know exactly what size you need unless you first test-drive a few pairs.

A Red Wing employee (name withheld) says it all:

“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 expand to fit your foot. While this suggestion may apply to other shoes made from inferior leather, Red Wings are manufactured with only the best leather and can’t be subjected to this deceptive tactic.

Step Two: Wear them at home

The second step is to wear your new Red Wings at home for an hour or two a day for one week. Your new shoes will be painful in the beginning, but at least you can take them off when they become uncomfortable—if you’re wearing them at home.

One (obvious) advantage of wearing these shoes at home is that you can admire them for just a little longer before their newness wears off. You will never see them in this state again, so enjoy it while you can!

Step Three: Wear them with your thickest socks

Like the human skin, leather responds best to gradual stretching. If you do not expand the leather slowly enough, it will be weakened at the seams.

Donning thick socks can help prevent the formation of blisters and hot spots on your feet. If you do get a blister, slap a Band-Aid on it to avert infection and provide yourself with extra comfort.

Step Four: Condition the leather

The fourth step is conditioning the leather. Leather is a type of skin like your own. Moisturize it occasionally to keep it supple and extend its life (especially if you live in a rough climate with rain, snow, and salt on the roads).

Red Wing Shoe Company recommends conditioning your boots after 100 wears or so to extend their lifespan, soften them and make them more comfortable during the break-in period.

What to not do when breaking in red Wings

Shoes and boots need time to break in, but you can make this easier on yourself by avoiding these things:

Do NOT dunk your boots in a tub of water.

Never dunk your Red Wings in water for an extended period in an attempt to soften the leather. While many people believe that immersing boots in water will soften the leather, the opposite is the case. Soaking Red Boots causes their leather uppers and soles to shrink and warp.

Do NOT blast your new boots with a hairdryer.

Heat will make leather pliable, but if exposed to heat for too long, it will dry out and crack.

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

Wearing wet socks can soften the leather and make the break-in period more comfortable, but it will also guarantee painful blisters that will make the process drag on even longer. And who wants foot blisters in this day and age of inflation-induced problems?

Do NOT go without socks either.

This allows the leather to form more precisely to the shape of your foot, but it also strains the feet and slows down the break-in process.

So, What Does Red Wing 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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