Sacre Bleu Wine has a sweet article about cigars, wine, and the new American cool.  A lot of the post focuses on the marketing job that CAO cigars has done to position them as cool with the millennium gen crowd.  Both wine and cigars have been trying to appeal to the new generation.  From the article -

While wine’s image is undergoing a makeover with millennials in terms
of stripping away the snob aspects, the image of the cigar smoker as
the atypical middle aged male is in bit of a transformation as well.  CAO Cigars
is a example of that movement.  It’s hard to argue with the image of
cigars on tour.  Band’s go on tour, why not cigars?  A recent “‘CAO
Flavourettes Tour’ featured the obligatory Flavourettes Girls as well
as a serious dash of product education.

I have a couple of thoughts about this issue.  First, I think that companies like CAO have done a better job than most in the wine industry at successfully marketing themselves as being cool.  The second thought that I have is that wine makers are in a very difficult position in this situation.  There are a lot of wines out there that really just seem to be trying too hard.  There is such a fine line between aggressively marketing "cool" without also marketing "trashy".  Finding the point where you can appeal to the desire for "cool" without sacrificing the dignity of the brand is a tough task.

I'd be interested to know if anyone has some ideas of wineries who are successfully striking the balance between cool and desperate.  I think that there are probably a lot of smaller wineries who are accomplishing this, but I haven't really seen very many good examples of this among the major brands.  I would love examples of small wineries who are tapping into this market.  I have my thoughts about a few, but would love to see what you all have to say.