The earliest Smartphones ran PalmOS, first the pdQ from Qualcomm, which was pretty ugly. But I thought the early series from Samsung were particularly fugly, the i300 and i330.
However, note the touchscreen-ONLY dialpad... something that was hated then, but of course now, accepted by milliions of HTC and Apple customers.
The successor, the i500, in contrast, was a wonderful PalmOS smartphone, both in function and in form (it was a flipphone... too bad no more smartflips these days... the last credible one from HTC was the StarTrek/3125).