I'm a subscriber to Barefoot Ted's huaraches Google Group, and the other day one of the members started a thread about funny comments and retorts which I thought I'd share in summary:

OrionFyre:

I got stopped by a cop who pulled up along side me to see if I was OK.
"why do you ask?" I say.
"Because you're not wearing shoes..." he replies
I look down at my feet with a look of surprise. "Oh shit! they must have fallen off."
I stand upright and look back the way I had came covering my eyes from the suns glare. In the corner of my eye I see the cop turn around in the car and look back.
"dammit." I mumble aloud
"I knew I should have tied them tighter."

OrionFyre:

Then a nice lady about my mother's age in a van was waiting to turn right when I was crossing She too asks if I was OK. "yeah why?" I ask.
"because you don't have no shoes."
"of course I don't"
"why not?"
"because I traded them for this jacket."
"why would you do that?"
"ummm because it's going to be winter soon and I don't want to get cold..."

OrionFyre:

A guy was in his front lawn raking the leaves, he too took concern for my well being.
"son you OK?"
"yep"
"how come you ain't got no shoes on?"
"I have shoes on...." I say with a confused look.
"no son, no you don't you're barefoot"
I look down and wiggle my toes. "No I'm not."
I can only imagine the look on his face as I walked away.

OrionFyre:

Cop #2 stops and asks if I'm OK. Alright, now this is getting old....
"yeah I'm OK."
"there a reason you aren't wearing any shoes?"
"of course." I say with a full stop. he looks at me as if to say 'annnnd that reason?' I continue "well my friend diagnosed with herpes so I gave him my shoes." again a full stop
".....O...K...."
"Anything else officer?" he shakes his head no. "have a great day" I say and wave.

Matt Mahoney:

So I'm standing at the start of an open 5K cross country race. "I have this recurring nightmare", I say to the runner next to me, "that I'm standing at the start of a race and just as they are about to say 'go', I realize I forgot my shoes".
I look down at my bare feet.
"But don't worry. I always wake up just before the race starts".

OrionFyre:

I went for a walk/run this morning around the mountain bike course. I saw this guy through the trees catching up to me pretty quick running. I was taking a nice leisurely pace as my feet were sorta sore from 12 miles of walking on concrete and gravel and blacktop yesterday. Once he swings around onto the path I'm on I hear his pace slow up.

He comes up next to me "how ya doin?" he asks. "doing good" I say and smile politely.
"mind if I ask you a question?" he asks, "sure..." I glance down at his shoes. "wait, how come you're wearing shoes!?!?"

He gave me a look like 'OK...'
"no for real" I continue "how come you're wearing shoes?"
"because.... I don't wanna hurt my feet...."
"oh OK... oh sorry, what were you gonna ask?"
"I was gonna ask how come you're barefoot."
"oh that's an easy one." I say with a full stop.
We go about another hundred feet before he prods for more "so why ARE you barefoot."
I shrug "I don't wanna hurt my feet."

And of course my own experience...

The closest I've had was one mum called be "barking mad" and another, whilst I was out running in the rain, shouted "You've left your shoes behind", to which I replied "At least they're not getting wet" as I padded along barefoot enjoying splashing in the puddles like a child.