I was at a wedding this weekend and two attendees were wearing the same model of shoes I was - color 8 full straps. Good stuff
Given how little I wear boots nowadays, I'm trying to whittle my boot collection down to three... Pick two of these four to sell:
Color 8 Wingtip Boot
These are all for weekend / casual wear from fall through spring. All are on commando.
I would say it depends on what other shoes you have that aren't boots. If you have wingtip shoes then the wingtip boots become less of a necessity, if you have split toe shoes then the tanker becomes less of a necessity.
Just from the information you gave I'd say sell the CXL indys and keep the rest (since you have cigar indy's already).