I would agree that there still is a stereotype here...I am 34 and still get looks when smoking bigger stogies like you have both described, but there is a growing number of younger smokers as I have seen from the clients and staff of my local shops. Of course here in San Antonio, we also have local anti smoking laws that don't allow smoking in establishments that sell food unless they have completely different rooms available for smokers...which a lot of them don't...so really I end up smoking mostly at home or outdoor functions.

I would say here the anti smoking stigma is worse than any stereotypes of cigar smokers as far as interupting my enjoyment of smoking cigars.