Once you get the hang of it, cutting a cigar is easy. There are several methods, and as you try them you'll find one that you favor over others. Here are some basic descriptions, along with the pros and cons of each cigar cutter design.
Guillotine - The most common cut is made by a double- or single-blade guillotine cutter. Usually, this is used to cut only a portion of the cap off (just enough to expose the inner binder and filler.) You should see one or several lines around the diameter of the head of the cigar -- this is the cap. Cut above the topmost line to avoid unraveling the wrapper at the head. The cap should be almost flush with the blade when you make your cut so that the cap is not completely removed. Pros: Cuts a large portion of the cap to reveal the full diameter of the cigar for maximum airflow and smoke density. Cons: Compromises the structural rigidity of the cap if not used correctly. An improperly cut cigar using a guillotine will make the wrapper unravel.
V-Cutter - Another popular tool is the V-cutter, designed to cut a small V-shaped slit in the cap of the cigar so that the cap and wrapper remain intact. A V-cutter is simple to use since the cigar is resting in a inverse dome on the cutter to support the cigar while you are cutting it. It is also superior to the guillotine cutter in maintaining construction since a smaller portion of the cigar is being cut. Pros: Easy to use. Maintains the overall shape and structural integrity of the cigar and cap. Cons: Only opens a small slit in the cap which may cause a hotter smoke and also collect tar more readily, resulting in a bitter taste if you are hard-drawer. Does not have the ease of draw and combustion qualities of a full guillotine cut.
Punch Cutter - Punch cutters are also very popular due to their small size and ease of use. A sharpened cylinder or "punch" simply cuts out a small hole in the cap of the cigar, which makes this cutter the best for maintaining the overall integrity of the cigar. Many punches come on key chains, guaranteeing that you will never be with out your cutter... so long as you remember your keys! Pros: Portable. Maintains the cap of the cigar better than a V or guillotine cutter. Easy to use. Cons: Like the V cutter, the small punch hole can sometimes cause the cigar to smoke "hot" and build tar within the hole. Creates a hard draw on larger cigars.
Scissors - If you are just itching for an old school cigar cutting experience, there is nothing better than a cigar-specific scissor for your stogies. Proper use requires a delicate and experienced touch, but the payoff is huge. Scissors afford you the versatility to adapt to any size or shape of cigar instead of being limited to the diameter of the cutting area like on a V-cutter or guillotine cutter. With the prevalence of large ring gauge guillotine cutters now on the market, the benefit of a scissor type cutter becomes less apparent, but just like shaving with a straight razor, it's more about the experience than the actual result. A scissor cutter in the right hands will create a clean, open cut while making the operator look like a tried and true cigar expert. Pros: Can adapt to any cigar size. Old school flair. Cons: Higher learning curve. More advanced cutters work just as well without being difficult to use.
Teeth - You'll see people doing the chomp-cut in the movies, but unless you want tobacco salad on the end of your cigar, we recommend you would avoid this method at all costs. I have seen some smokers rotate the cigar on their canine and make a perfect cut, but unless you smoke many cigars each day, I would stick the proven methods. Pros: It looks cool when done correctly. No need to have a cutter on hand. Cons: Can turn your expensive cigar into a salad of wet tobacco. Picking tobacco out of your teeth. Stained teeth.