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When I was in the military, we kept the shoe trees in the shoes all the time when they weren't being worn. It helped make it easier to polish them and helped them dry out. Given the heat and the sweat poured into them, you didn't want the leather to shrink as they dried. Once the shoes are dry, there really isn't a need to leave them in. You should leave the trees in your shoes all the time that you are not wearing them. If you don't, over time, the front of the shoe starts to bend upwards. To protect the shoes and keep them in good shape for a long period of time, leave the trees in them all the time. A new type of shoe tree actually came out about 2 years ago that is a wearable version of the standard cedar shoe tree. You can find them at www.wearableshoetrees.com, but their version is made out of a soft plastic and looks like an inner shell. I know that they offer different sizes, so I bought a larger size than I typically need, so it worked like a shoe stretcher too! I know you can find reviews on Google if you type "decreaser" because that's what all the sneakerheads are calling it right now.

But to answer the original question, you can leave the wearable shoe trees in ALL the time without having to take them out to put your shoes on.

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Q: Should shoe trees be kept in the shoe all the time or just for a short time after a shoe is worn?
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