It's about screen size!
While a lot of the other factors discussed above have been important, a large part of the "cool/uncool" issue - and the very real usability issue - is because MS has allowed the physical platform to get away from it by not requiring screens at least as large as for the original non-telephone Pocket PCs for full WM phones.
In the absence of a "full-size screen" requirement, the phone companies have been able to limit the available devices to smaller screens. This has simultaneously reduced usability without a stylus, readability of text, and coolness.
I'm still using an HTC-designed Verizon XV-6600 running the six-year-old PPC 2003 2nd Edition, because I refuse to move to a smaller screen. Instead, I buy a new rebuilt XV-6600 online every so often (usually in pairs, out of fear that it may be my last chance to do so), since devices this small and complex seldom last even a year of use.
Just the same, I'm often asked "Is that an iPhone?" because it has a large screen. My stock response is, "No, it's an Old Phone - you can't get one like this any more except second-hand."
Still have a few stockpiled against this one's failure. I get a new battery every time I buy one - I'm up around six or so (plus the ones I've discarded because they wouldn't hold a charge any more).
If the Samsung Omnia II becomes available soon, I'll upgrade. I'll probably revert it to the standard Today screen, and then install spb Pocket Plus to make it the way I want it.
And I'll only have had to wait six or seven years to upgrade!
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