I agree with what people have said about the Indy boot being most appropriate with jeans. It does look rather utilitarian, and as such I find the commando sole the perfect match for it (i.e. any of the LS Ultimate Indy's). My cigar Indy's get the most wear almost strictly for the versatility of the commando sole; that and I wear jeans seven days a week.
would be great to see some pics of your commando sole cigar indys with jeans. I currently only own the standard 405 indys - I love them as I can wear them the entire weekdays to work with jeans as well but when the need for dressier occasions arises I find them difficult to wear. Looking to get a pair of shell boots (cigar or ravello) but still cannot decide on which one. The cigar indys could be a likely candidate but not sure if i should go for commando or double leather soles. thanks in advance.