I wouldn't put anything on them that blocks the pores from breathing. I've had all kinds of boots in my life and the best ones needed very little, if any waterproofing. My suggestion might be a bit extreme, but you might want to wet a pair of socks, put them on and wear the boots dry. In the old days I once poured hot water into one boot, then transferred that water to the other boot, emptied that boot and wore them dry. I slept in them for a day or two, and they never hurt my feet. These days that would be problematic given all the plastics and membranes in boots. Also get a pair of "superfeet" insoles...nothing better except custom insoles and only about 30 bucks.

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Everyone so far has outlined in sufficient detail step 2 of the breaking in process - mink oil. Step 1, though, is equally as important to start the breaking-in process - Showering in your boots. You wear the boots in the shower, get them good and soaked, and them wear them around for a couple hours. If you dry them off with a towel after the shower, they shouldn't track water all over your house. If you want to play it safe, just plan on wearing them around outside for a while. Mink oil will help with the leather boot body and upper, but it will do nothing for the insole. Step 1 will break in your entire boot, not just the leather. When done, allow them dry in front of a fan or space heater. Be careful though, you don't want to leave them in front of a fan overnight as they can dry out too much and become brittle. The drying process is most important for the insole so that you don't get mildew in there. As the boots are drying, intermittently apply mink oil generously. After this Step 1, only use the mink oil. Don't shower in them again, unless that's your thing. I won't judge.

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It all depends on the type leather your boots are made of that determines the best course of action for break-in and care. Red Wing has the suggestions on the inside of the box.

Mink oil is definitely a good start. But for an investment like a pair of Red Wings, you have to go with Obenauf. Without a Doubt!

Obenauf's Leather Conditioner Oil

Obenaufs HD Leather Preservative

I have worked in some of the harshest conditions on a construction site and my boots are like little tanks.
@Chris Campbell- I have the same boots. Great traction for decking. Love em.

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A process that has been used previously but fallen out of favor recently is soaking the boots in warm water and wearing them for several hours consecutively. Because the leather is wet it begins to conform to the structure of your sole/foot, eventually forming an excellent glove like fit. This method is really only effective if you have the opportunity to walk around (preferably outdoors) for several hours in wet boots. Also, it is extremely important that applications of Mink-Oil or another leather conditioner are used frequently, this will extend the life of your boots exponentially.

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put a pair of thick socks on, then put the boots on. get the boots wet wear them around the yard or where ever you want to until they are dry. do that a few times and they will break in just fine. but the boots have to fit perfectly to your foot. it they are uncomfortable and are tight in certain spots, keep searching for some footwear.

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