I have two pairs of Classics: the mauve/sand upper, grey bottom and the black on black.
I find them to be my favourite VFFs for walking around town if I want a shoe for warmer weather, like sandals. They are incredibly easy to slip on, have never fallen off my feet, and I love the look of them. I love the look of them so much that I have been known to wear the all black pair while wearing a cocktail dress to a New Year's Eve party as well as a beach party in the middle of winter (in a heated tent).
These were the shoes that I competed my second sprint triathlon in and found them to be a wonderful transition as well as running shoe (although I recommend Vaseline on your toes if you're going to run a reasonable distance).
I find the Classics slightly less comfortable than my KSOs for longer durations of wear because the toes are a little tighter, which helps them stay on, but makes them less comfortable at the same time.
I have recently discovered a modification that makes the upper more comfortable for me too: I removed the elastic cord. I found that I didn't need to tighten it at all for the shoe to stay on my foot, and it could dig on the top of my foot when worn for a long time, so I cut it out. I've worm both of my pairs of Classics like this and enjoy them even more than before.
I don't find that the high back on the achilles tendon is irritating in any way, which is what I thought I'd find when first seeing them.
They are comfortable enough that I have forgotten that I'm wearing them, until someone sees them and stares or asks a question about them, which happens about every second time I wear them in public. Now that it is finally getting warmer here, I'll be wearing the Classics a lot more often.
