https://bugs.winehq.org/show_bug.cgi?id=44759
--- Comment #6 from Nikolay Sivov bunglehead@gmail.com --- (In reply to Anthony Jagers from comment #5)
I've always had this problem out of steam under wine. Italic fonts. I never had a clue to what could be causing it. But, I just lived with it. It's much older than wine 3.x releases.\
So you still have it with latest Wine? Normally UI is using Tahoma I think, but it's possible it could use different font, if it finds it. For example, if it used family name SomefontFamily and you have only italic variant of it available, that's what dwrite will use, even if asked for regular style. That's normal.
Could you attach +dwrite,+dwrite_file log if you still can reproduce, and also please export Windows NT/Fonts registry key and attach it here.