To install:

• brew cask install xquartz
• brew install wine
• brew install winetricks

Configure wine:

• winetricks fontsmooth=bgr (winetricks fontsmooth=rgb worked just as well). This part is essential. Without it, the font display is truly awful.
• to get all config options, run winetricks settings list

To run an executable:

• wine regedit or wine ~/Downloads/SumatraPDF.exe

I also tried latest CrossOver, but it has infuriating UI.

Wine on mac has 2 display drivers: native and using x11.

Native is used by default. We installed wine with --without-x11 flag to disable x11 display driver completely. Without that wine will insist on installing x11 server (either via brew cask install xquartz or from https://www.xquartz.org/).

I don't know which driver is better.

If you install xquartz you can switch the driver with winetricks macdriver=x11 (and switch back with winetrics macdriver=mac

alldlls=builtin          Override most common DLLs to builtin
alldlls=default          Remove all DLL overrides
ao=disabled              Disable AlwaysOffscreen (default)
ao=enabled               Enable AlwaysOffscreen
bad                      Fake verb that always returns false
cfc=disable              Disable CheckFloatConstants (default)
cfc=enabled              Enable CheckFloatConstants
csmt=off                 Disable Command Stream Multithreading (default)
csmt=on                  Enable Command Stream Multithreading
ddr=gdi                  Set DirectDrawRenderer to gdi
ddr=opengl               Set DirectDrawRenderer to opengl
fontfix                  Check for broken fonts
fontsmooth=bgr           Enable subpixel font smoothing for BGR LCDs
fontsmooth=disable       Disable font smoothing
fontsmooth=gray          Enable subpixel font smoothing
fontsmooth=rgb           Enable subpixel font smoothing for RGB LCDs
forcemono                Force using Mono instead of .NET (for debugging)
glsl=disabled            Disable GLSL shaders, use ARB shaders (faster, but sometimes breaks)
glsl=enabled             Enable GLSL shaders (default)
good                     Fake verb that always returns true
grabfullscreen=n         Disable cursor clipping for full-screen windows (default)
grabfullscreen=y         Force cursor clipping for full-screen windows (needed by some games)
gsm=0                    Set MaxShaderModelGS to 0
gsm=1                    Set MaxShaderModelGS to 1
gsm=2                    Set MaxShaderModelGS to 2
gsm=3                    Set MaxShaderModelGS to 3
heapcheck                Enable heap checking with GlobalFlag
hidewineexports=disable  Disable hiding Wine exports from applications (wine-staging)
hidewineexports=enable   Enable hiding Wine exports from applications (wine-staging)
hosts                    Add empty C:\windows\system32\drivers\etc\{hosts,services} files
macdriver=mac            Enable the Mac native Quartz driver (default)
macdriver=x11            Disable the Mac native Quartz driver, use X11 instead
multisampling=disabled   Disable Direct3D multisampling
multisampling=enabled    Enable Direct3D multisampling
mwo=disable              Set DirectInput MouseWarpOverride to disable
mwo=enabled              Set DirectInput MouseWarpOverride to enabled (default)
mwo=force                Set DirectInput MouseWarpOverride to force (needed by some games)
native_mdac              Override odbc32, odbccp32 and oledb32
native_oleaut32          Override oleaut32
nocrashdialog            Disable crash dialog
npm=repack               Set NonPower2Mode to repack
nt40                     Set windows version to Windows NT 4.0
orm=backbuffer           Set OffscreenRenderingMode=backbuffer
orm=fbo                  Set OffscreenRenderingMode=fbo (default)
psm=0                    Set MaxShaderModelPS to 0
psm=1                    Set MaxShaderModelPS to 1
psm=2                    Set MaxShaderModelPS to 2
psm=3                    Set MaxShaderModelPS to 3
remove_mono              Remove builtin wine-mono
rtlm=auto                Set RenderTargetLockMode to auto (default)
rtlm=disabled            Set RenderTargetLockMode to disabled
rtlm=readdraw            Set RenderTargetLockMode to readdraw
rtlm=readtex             Set RenderTargetLockMode to readtex
rtlm=texdraw             Set RenderTargetLockMode to texdraw
rtlm=textex              Set RenderTargetLockMode to textex
sandbox                  Sandbox the wineprefix - remove links to /Users/kjk
sound=alsa               Set sound driver to ALSA
sound=coreaudio          Set sound driver to Mac CoreAudio
sound=disabled           Set sound driver to disabled
sound=oss                Set sound driver to OSS
sound=pulse              Set sound driver to PulseAudio
strictdrawordering=disabled Disable StrictDrawOrdering (default)
strictdrawordering=enabled Enable StrictDrawOrdering
vd=1024x768              Enable virtual desktop, set size to 1024x768
vd=1280x1024             Enable virtual desktop, set size to 1280x1024
vd=1440x900              Enable virtual desktop, set size to 1440x900
vd=640x480               Enable virtual desktop, set size to 640x480
vd=800x600               Enable virtual desktop, set size to 800x600
vd=off                   Disable virtual desktop
videomemorysize=1024     Tell Wine your video card has 1024MB RAM
videomemorysize=2048     Tell Wine your video card has 2048MB RAM
videomemorysize=512      Tell Wine your video card has 512MB RAM
videomemorysize=default  Let Wine detect amount of video card memory
vista                    Set Windows version to Windows Vista
vsm=0                    Set MaxShaderModelVS to 0
vsm=1                    Set MaxShaderModelVS to 1
vsm=2                    Set MaxShaderModelVS to 2
vsm=3                    Set MaxShaderModelVS to 3
win10                    Set Windows version to Windows 10
win2k                    Set Windows version to Windows 2000
win2k3                   Set Windows version to Windows 2003
win2k8                   Set Windows version to Windows 2008 R2
win31                    Set Windows version to Windows 3.1
win7                     Set Windows version to Windows 7
win8                     Set Windows version to Windows 8
win81                    Set Windows version to Windows 8.1
win95                    Set Windows version to Windows 95
win98                    Set Windows version to Windows 98
windowmanagerdecorated=n Prevent the window manager from decorating windows
windowmanagerdecorated=y Allow the window manager to decorate windows (default)
windowmanagermanaged=n   Prevent the window manager from controlling windows
windowmanagermanaged=y   Allow the window manager to control windows (default)
winver=                  Set Windows version to default (win7)
winxp                    Set Windows version to Windows XP