Replacing My Converse: Keen + Inserts

A month ago I went to the doctor with ankle pain, pain I assumed was caused from either skating or the running regimen I’d started. Come to find out, the culprit was more likely my beloved Converse. Years of wearing shoes with no arches had strained my achilles tendon. Sadly, it was time to replace my Converse.

To the internet I went, desperately trying to find a pair of shoes similar to my Chucks, but with an arch. I found four viable alternatives. After looking at color options and watching videos on Zappos, I decided to go with the Keen Maderas Lace.

How Do They Look?

Not identical, but inspired by.

Not identical, but inspired by.

Looks wise, they’re very similar to my Converse. I went with gray because that’s what my Converse were. They’re not going to be mistaken for the classic Chuck Taylors, but you can definitely see the influence. They have more details on the side, and a shorter toe cover, but have a very Converse like “feel” in the looks department.

These are also vulcanized shoes, meaning they’re fused with heat instead of glue. One problem I’ve always had with vulcanized shoes is they heel starts to fold, and then gets a tear. This was happening with the Keens as well. Although it may be the way I walk (but more on that later).

How Do They Feel?

Check out that arch!

Check out that arch!

The first time I put these on, I felt like I had a lump in my shoe. The arch has that much of a difference from the Converse. After I adjusted, they felt comfortable. It wasn’t until I was on my feet for a long period of time that I noticed I was getting ankle/arch pain. Although this time the pain felt like it was beginning from the heel. I started paying attention to the way I walk and noticed I have an extra heavy heel strike. While the arches are better in the Keen Madras, the shock absorption seems to be worse.

Now What?


After realizing that I have a hard heel strike, the next step was to get inserts. I was purposely trying to avoid this, but it’s just not possible for me. Thankfully, since I had a good foundation for the arch, I could get away with less expensive inserts.

I went with the Dr. Scholl’s Active Inserts. They’re made to add extra cushion for athletic shoes, so I knew they could handle what I’d throw at them. They added even more arch support, and extra heel cushion. Plus, the heel is “cupped” almost giving more support to the shoe itself in the back. This prevents the folding issue I talked about before.

Did It Work?

A combination of shoes, athletic tape, and rest have greatly reduced the pain I feel in my ankle. Its almost not existent now, and only triggered after lots and lots of walking.

Best Option?

If you’re looking to make your Converse more foot friendly, you may be able to get away with just the inserts. If my existing Converse weren’t so beat up (the toe was starting to crack) I would have tried this first. But if you’re in the market for new shoes, I suggest giving the Keen Madera Lace a try. They’re available in both men’s and women’s. Plus if you order from Amazon they have free returns (and we’re affiliates so clicking on the link from here supports us as well).

Update: I’ve found going up a half size in my converse, and then buying the Dr. Scholl’s Tri-Comfort insoles has worked very well for me!

One Response to “Replacing My Converse: Keen + Inserts”
  1. Erin says:

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