https://bugs.winehq.org/show_bug.cgi?id=41639
--- Comment #20 from Roman Valls brainstorm@nopcode.org --- Unfortunately on OSX, even using brew-installed Freetype 2.9.1:
$ brew info freetype freetype: stable 2.9.1 (bottled) Software library to render fonts https://www.freetype.org/ /usr/local/Cellar/freetype/2.9.1 (60 files, 2.6MB) * Poured from bottle on 2018-10-20 at 00:10:40 From: https://github.com/Homebrew/homebrew-core/blob/master/Formula/freetype.rb ==> Dependencies Required: libpng ✔
And Wine 3.18:
$ brew cask info wine-devel wine-devel: 3.18 https://wiki.winehq.org/MacOS /usr/local/Caskroom/wine-devel/3.18 (120.9MB) From: https://github.com/Homebrew/homebrew-cask-versions/blob/master/Casks/wine-de... ==> Name WineHQ-devel ==> Artifacts winehq-devel-3.18.pkg (Pkg) ==> Caveats wine-devel installs support for running 64 bit applications in Wine, which is considered experimental. If you do not want 64 bit support, you should download and install the wine-devel package manually.
Fonts still don't look good at all... I guess that XQuartz is the culprit now since it has not been updated/released since 2016?.