There are two kinds of ugly boots. Here are some examples of the pretty and wearable kind. These two by asos:
...And the preferable, non-wedge topshop version:
These office shoes present an appropriate ugly-boot alternative.
There are, unfortunately, those kinds of ugly-boots which have ventured too far into the ugly realm: Bearded Tramp Boot, topshop ('argyle sock lined ankle boots').
Oh, and anything by Ugg crossed the line between Ugly and Too Ugly years ago.
On Saturday I'm going to stay in Brighton for two weeks. It has loads of vintage shops so one might presume I would be excited. However through recent experiences I have come to realise that vintage clothes, from pretty much any decade, are hideously ugly. So, unless I can develop an interest in overpriced silk scarves and clock pendants (the only mildy acceptable items available) that lasts for two weeks, I may have to spend the majority of my time in topshop or mac.