Depends what you want to wear them with. As mentioned before, I have a pair of cap-toes in cigar and it is both richer and lighter than it appears on that site. It is literally the colour of a cigar. Alden pair cigar with the lighter 'plywood' looking soles. So, overall, cigar is more casual - in fact, I feel it a little casual for my workplace - though I do wear it with mid greys and my one 'lighter' navy. The #8, however, you could wear with just about anything...hard to get a matching belt though. I wonder why they are different prices?