Achilles Pain w/ Shoes- Any advice?

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Anyone ever had an issue like this?  Would appreciate any advice.

I've started to have a sharp pain in my left achilles, but only when I'm wearing shoes.  It feels a little like wearing shoes that are scraping or poking against the area, except it's actually been worst when wearing the Nike Free 3.0 Flyknits, which basically have nothing back there except cloth.  I can barely walk around in those at this point.  

I've started to wear some of my older Nike frees, which actually have some support, and it feels better, but is still a little painful.  (I'm not a sneakerhead like most of you all, and I actually don't even know that many shoes—plus they're almost all low tops).

The funny thing is that it feels completely fine when I'm barefoot, even though it's worst in the shoes I have that are closest to barefoot.  Can't figure it out.

In terms of activity I do crossfit, not a ton of running but did do a fair amount of it the other day soon before it flared up.  Still, I didn't feel any pain during or immediately after the workout, when I was wearing running shoes that are less painful.  I'm not sure if it's from exercise, the shoes I'm wearing, or what...  And how to proceed.

Right now I have it iced and elevated, even though it feels absolutely fine walking around at home without shoes on.  Damn shame because I love those flyknit shoes, too.
 
Something in your gait may not vibe with the shoe?

Could be as simple as the support of the shoe vs the shape of your foot/heel.

Once soreness begins, probably just feeling residual pain in older, "more comfortable" shoes.

If you stop wearing the problem shoe, should get back to normal in a few days. If it persists beyond that, have it checked out.
 
See if you get heel lift as you play. I had the issue with basketball sneakers that were too large and I would get heel lift. It led to two issues, achilles pain and planter fasciatus (or however you spell it). As soon as I switched shoes I was okay after about 2-3 weeks.
 
Thanks for the comments so far.  I'm gonna try lying down like Melo.  Giving this one final bump.
 
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