Last year I bought the Blundstone 500 pull-on boot.
That is a very comfortable and waterproof boot. But looks like a cutoff gum boot.

This boot on the other hand has good styling.
It is a bit tight over the top of my foot, but I have high arches. To put this in context, the 500 boot is same size but not even a little bit tight.

This boot looks good enough to wear around town. Not quite as comfortable as the 500 but still very good.
I have been wearing it for a couple of months now and it gets better every time I wear it..