Fashion is not something standalone; it is a sum total of many heterogeneous things taken together. That brings in your clothes, your personality, your charm and your tastes together and a manifestation of all that are mentioned occurs through how you carry them. That makes your choice of wine in a party as a determinant of whether you are fit to be wooed or booed at; the same goes for the cigars, keeping personal preference aside.

There are certain guidelines one must follow to optimize an overall cigar-smoking experience when there are alcoholic beverages present and one doesn’t necessarily want to be a beetle when it’s outside his bedroom.
Like certain types of food complement certain wines, similarly, certain types of wines also complement certain cigars and vice-versa. The taste and flavor of cigars can be used to stimulate the taste buds (also the nervous system) and that explains why it’s so important to create a proper match.
Let’s start with the white wines. They are more difficult pairing with cigars than red wines, especially because white wines are usually mild-flavored and dry. The cigar finds it easy overwhelming the taste and flavor of the wine. Thus, a sweeter white wine (e.g. Pinot Grigio, Pighin, Santa Margherita) is found to be a better match for mild to medium bodied cigars; the wines more on the sweeter side also offer a slight fruity taste that the cigar’s smoke can’t wash out completely. A second option would be Chardonnay.
Coming to the red wines, the variety offered is greater than that in the whites because of more pungent and intense tastes. Thus comes the risk of the cigar getting overwhelmed by the wine, so one needs to strike a fine balance according to his taste. For example, Italian reds (Pinot Noir or the Zinfandels or Sangria) offer interesting mixes but the Boonesfarm do not; neither does the Merlots to most of the connoisseurs.
However, a personal preference always stays at the front but experimentations on that ground are restricted to your drawing room or at the cigar bars and wine tasting parties. If you are not sure about the pairing, an easy way out is Sherry. The luxurious, nutty flavors that are not too dry are perfect for medium-bodied cigars, while with the old classic Brandies, nothing proves as good as a full-bodied cigar. For milder Brandies, it’s always the milder cigars and for whisky, it’s the same rule that applies.
Beer drinkers, sorry to keep you waiting, but you may welcome any cigar that you may like with the Ales and Lagers; the darker they are, the better. Tequilas are better with Mexican cigars while with rum; it’s the beer rule that holds.
To end in a perfect note, just make sure that your drink is not too cold; coldness numbs the taste buds and ruin an experience.