I’m sure I could produce an “Ugly Pen of the Month” every month without any difficulty. However, the ugliest pens I see around these days tend to be modern. Some of those pen manufacturers employ aggressive and vicious ninjalawyers who would sue me back to the Stone Age if I were to criticise their expensively designed horrors. So I won’t.
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Goodwriterspens's Blog 
Cheap pens from the 1950s & 60s it is then! Mind you, the Parker 25 is still great. Odd but great. I use mine on site visits as its indestructible.
As I discovered when I was unkind about the Parker 25, ugly is in the eye of the beholder. There are some curious hooded-nib Wyverns and Mentmores from the post-war period that I rather like but some other people detest. There are some modern pens that have such folderols and excrescences that I believe they can be described as nothing other than ugly but I dare not name names. I’m sure you can think of a few yourself.
one contentious design from the late 1980/1990 period might be the alleged Bauhaus inspired Rotring Newton 600 – with its silver coloured hexagonal barrel. I do have one in fact, but only because it came very cheaply in comparison with ebay prices, but suppose you either love or loathe the shape.
Believe the model has been defunct for some time.
The P25 Flighter is a good pen for the money, and I have a white one as well – but again it’s a modern design and perhaps I’m just old fashioned:)
The Rotring is odd but I don’t think of it as ugly. It reminds me of some modern mechanical pencils. I agree that the Parker 25 is quite a good pen but I don’t care for its looks.