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How to Break in Red Wing Boots? Easy and Pain-free Methods

Fact checked by Andrew Carnegie

how to break in red wing boots

It is normal to find that your newly bought Red Wing boots are not as superb and comfortable as promised. Similar to most safety footwear, Red Wings require a break-in period to conform to your foot shape. Typically, this process takes up to three weeks. So, how to break in Red Wing boots efficiently?

You need well-fitted boots to begin with. On the first day, wear them indoors for a few hours. When your feet grow accustomed to the boots, you can wear them outdoors. To further stretch the leather, pair the boots with thick socks, bend them back and forth, and rub on leather conditioners. Finally, store them in shoe stretchers for the best results. Dive in for a step-by-step guide!

What to Prepare


Red Wing is well-known for its sturdy and long-lasting products that can protect your feet from the most dangerous hazards. Hence, skipping Red Wing boots’ break-in period and wearing them straight to work might cause serious damage to your feet, ankles, and knees. Besides flesh wounds and bruises, you might develop more severe symptoms like constant foot pain, deformities, or even neuropathy.

No worries, though. With correct practices, your heavy-duty boots will become your best ally on the job site. You will need the following to make the break-in process faster and easier.

1. Thick socks

You should have nice and comfy thick socks handy. They will prevent your feet from direct contact with the stiff leather and soles while forcing the shoes to stretch a bit further. You can wear two regular socks in replacement of a thick one. But they have to feel comfortable and breathable.

Note that socks do come in different sizes. Measure your feet to get the right fitting. Also, keep in mind that polyester and merino wool are more stretchy and moisture-wicking than cotton.

2. Leather cream or mink oil

Leather care products will help soften the rigid leather parts near the heels and toes. But don’t forget to check the label before purchasing. For instance, the upper material of the iconic Red Wing Iron Ranger is full-grain leather, while that of Red Wing King Toe is waterproof nubuck. The two require different conditioner types.

3. Shoe stretchers

If you have a difficult time finding the right boot size, stretchers will be a well-paid investment. They can help size up work boots and the rest of your shoe cabinet. The best part is they are simple to set up and will speed up the break-in process. In addition, some shoe stretchers can target problem areas. Let say your Red Wing boots fit snugly but feel tight just around the heels, a stretcher can alleviate the issue.

Steps to Break in Red Wing Boots


1. Pick the style that suits your needs


Red Wing offers numerous styles with different protective functions. Check the table below for some safety properties the brand offers.

Firstly, pick the styles that meet your job safety requirements. Then, make sure they fit properly. If possible, try before you buy. Most Red Wing boots are true to size, but you should check the reviews on their website for specific information. When you try on the boots, they should fit, as follows:

  • There is enough room for your toes to wiggle freely. You should leave at least half an inch in the toe box.
  • The insteps fit snugly, not tightly. After standing or walking in the boots for a while, the sides of your feet don’t feel tingly.
  • The heels should never cause slippage, especially when you’re buying trekking or logger boots.

If you have one of these problems, return the shoes and ask for a half to one size bigger. Breaking in a wrong fit is painful and tortuous. Plus, no amount of break-in can fix overly tight shoes. In case you’re still unsure, go up half a size and choose a lacing style that allows you to adjust the fitting easily.

2. Wear the boots indoor

On the first day, pair the boots with your regular socks and wear them indoors for a few hours. Just do your daily tasks and avoid carrying heavy loads. Take note of where the boots hurt and stick a bandage to the area.

Normally, the little toes, heels, and areas near the heel counters might feel slightly uncomfortable. However, if there appear any bruises, damages on your toenail, or blisters on the skin, you should consider switching size or style.

3. Wear thick socks and go outdoors

Now, your feet are used to the heavy boots. Wear thick socks underneath them and take a walk outdoors. If the shoes are somewhat loose, insert heel and toe pads. Once you feel comfortable with walking, try jogging and doing short exercises like heel raises, lunges, and rocking your feet side to side. Nothing too crazy though, just make sure the boots can support your feet in various positions.

4. Bend the boots

Bend the boots with your hands to quicken the process. Don’t use too much force or you might crack the leather and rubber soles. Instead, gently bend them back and forth. Do this every day for at least a week to soften the leather. Some tough models like the Red Wing SUPERSOLE® or NAILSEAT might take longer to loosen.

5. Work in the leather conditioner

At this point, there might still be tough leather portions left, especially the fabric near the welt and heel counter. You should treat such areas with mink oil or leather cream, then pinch and massage them with your thumbs. This can increase the stretchiness of the fibers and aid in breaking in Red Wing boots more quickly

Also, when you notice tiny cracks or splits, immediately rub a decent amount of leather conditioner on the spots. Before applying leather care products, wipe the leather surfaces with a clean cloth or brush.

6. Use shoe stretchers

If you’re short on time and the steps above are too tedious, then shoe stretchers are your best way to break in Red Wing boots. Follow these steps to break in your boots with shoe stretchers:

  • Spray the shoe stretching solution generously on the inside and outside of the areas that need stretching. You can skip this step if you’ve already applied a shoe conditioner.
  • Wait two to three minutes for the liquid to absorb.
  • Expand the shoe stretchers as much as you desire and insert them into the Red Wing boots. You can stretch further by turning the knob, but stop when you feel resistance. Remember that leather naturally loosens over time, you don’t want to end up with roomy boots only after a short period of use.
  • The longer you leave them, the more the boots will stretch. We recommend leaving the stretchers overnight for about eight hours. Afterward, try them on and repeat the steps only if needed.

7. Take breaks

Avoid wearing your new boots many days in a row. If this is your first time wearing heavy-duty boots, your feet can feel weary and experience constant fatigue. Give them a break after a day or two. Additionally, the breaks allow the new leather to fully dry from perspiration, preventing bacteria growth. Storing the boots in shoe trees at night will also help.

It usually takes two to three weeks to break in safety boots. So, don’t rush the process. Once you have broken in Red Wing boots properly, they will feel much more comfortable and supportive. Check out this video for how to break in Red Wing Iron Ranger:

Lastly, avoid these break-in techniques:

  • Wearing soaking wet boots is not a good idea. The leather might loosen up a bit but it can cause fungal infections to your feet.
  • Using a hairdryer or external heat source will stiffen and shrink leather.
  • Leather is natural skin, so any type of alcohol will dry it out. Using rubbing alcohol to stretch leather only makes it vulnerable and prone to cracks.


Hopefully, this tutorial on how to break in red wing boots helps ease your feet into the heavy gear. While Red Wing is famous for its high-quality and enduring products, appropriate break-in plays a huge part, too. As a last reminder, work boots are the final line of defense for your feet when facing dangerous hazards, so make sure they are ready before wearing them to the worksite.

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