I have extremely flat feet. Standard arch support is basically out of the question for me. My feet are so flat that aggressive arch support feels like it is trying to bend my foot the wrong direction.

I have spent a small fortune on cycling shoes, and the problem is that I usually cannot know if a shoe will work until I clip in and pedal hard for 45+ minutes.

My issue is usually my left foot, specifically the outer two toes — pinky toe and the toe next to it. On longer rides, I eventually have to unclip, shake my foot around for 10 seconds, and then I’m good for a little while before it starts again.

It is not severe numbness, but it is enough to be uncomfortable and distracting. Generally, the stiffer the shoe, the worse it gets.

In MTB shoes, my all-time favorite is the Five Ten TrailCross Clipless. I never have comfort issues with them. They are hands down the most comfortable cycling shoes I have used. The downside is that they are clunky, heavy, and not great for power transfer.

For racing gravel and MTB, my favorite shoe so far is the Five Ten Kestrel BOA. It seems to hit the best balance for me: stiff enough to race, but not so stiff that my toes go completely numb. That said, I still get some numbness.

Also, I really dislike the closure system on the Kestrel BOA. It has one BOA near the top of the foot and Velcro straps over the rest. I wish it had better forefoot/midfoot lockdown. The shoe works best for me so far, but the single BOA/Velcro setup annoys me.

What I’ve tried

• A lot of shoes, including Lake. Too many to remember.
• Cleat placement in basically every position: all the way back, left, right, etc. Moving the cleats farther back does not seem to solve it.
• Platform-style clipless pedals, currently Shimano XTR XPD, which help a little by spreading pressure better.
• Insoles. So far I’ve tried Happy Feet, and this is where I’m currently focused.
• Saddle height, saddle position, general bike setup adjustments.

What I’m looking for

First: has anyone had this exact issue — very flat feet, outer toes going numb, worse with stiffer shoes — and actually solved it? I’m especially curious if the answer ended up being a specific insole, metatarsal pad, shoe shape, or some other fit detail.

Second: does anyone else like the Five Ten Kestrel BOA but found an alternative with better support/lockdown? I like the stiffness level and general feel, but I hate the single BOA plus Velcro closure. I want something with better forefoot stability without making the numbness worse. (Side note, I really love the Trek Metnet, and if the insole was the problem, and I fix that... I'd probably go with them because of the boa system)

I know the “correct” answer is probably a professional bike fitter, but good fitters are far away from me and expensive. I’m not against it, but I’m trying to narrow this down before spending even more money.