Even if you’re intimately familiar with the inside of cigars, having split countless White Owls, you don’t really know cigars. There’s recreation and then there’s connoisseurship. No one is suggesting you need be an expert overnight, but a little knowledge never hurt. Now you’ll be able to stunt at country clubs and boardroom meetings like the boss you know you are. Or are pretending to be with some key insider information.

We met with the professionals at Nat Sherman, makers of fine cigars (and cigarettes) since the 1930s, at the Nat Sherman Townhouse in New York (12 East 42nd Street). Sam Perry, veteran tobacconist, and Michael Herklots, Executive Director of Retail and Brand Development, walked us through the basics, the 10 Things Every Guy Should Know About Cigars.

How are cigars sized?

Sam: Cigars come in a variety of sizes, from half-coronas to coronas to robustos to churchills to double coronas.

Michael: There are factory names and company names. For example, the name of thatsize [see photo above] is a half-corona or petit corona—those are the classic names you would call that format. Like a Honda Civic is a coupe. Half-corona is coupe. That’s the Nat Sherman Vanderbilt, which is like the Civic. Lots of people make coronas. Lots of people make churchills. For example, the Sam, the special edition we created for Sam, is a toro. Six inches by 50 ring gauge—ring gauge is 64ths of an inch. But we call it “the Sam.”

How is a cigar constructed?

Michael: Remove the wrapper leaf, the outside of the cigar [far right of the photo above], and you find the binder [to the left of the wrapper in the photo above]. Then the filler leaves are inside of that. Two things make premium cigars premium: long filler and hand rolling. What that means is you have all these components that have been put together by hand. But this piece [center of the photo above] is the long filler piece. Any cigar that you might’ve taken apart with your friends, the inside probably didn’t look like this. For a cheap, machine-made cigar, the inside comes apart in little pieces. Short filler. Scraps.

Long filler is the guts of the blend. Different leaves from different countries from different positions on the tobacco plant. They’re put together so that the cigar burns evenly. If the filler is too thin, the cigar burns too hot. And then it’s not enjoyable. So, wrapper, filler, and binder. It could be all different countries, all different seed varieties, all different leaf positions.

How do the tobacco leaves used affect the cigar?

Sam: The top of the plant will be the strongest because it’s closest to the sun. We call that ligero. As you move down the plant, the flavors get milder. Next is viso, then seco, then volado. The strongest leaf is used as the middle because it burns slow. But it also burns harsh. All the layers around the middle create a way for you to draw without getting a harsh taste—you get the full flavor of the entire plant.

Michael: To blend, you have to use some ligero, because it gives you strength, body, intensity, and will slow combustion. The strongest tobaccos burn slower; they’re smaller and thicker. The secos and the velados get longer and thinner as you move down the plant. They’re going to burn faster, have less strength, but they’re great to add balance and stimulate combustion. If you made a cigar with all velado, it would burn super fast, super hot, and have no real body or flavor. It’d probably smell really nice, but that’s it. If you make a cigar that’s all ligero, it’s going to be strong as hell, it’ll burn super slow, if at all, and have no finesse.

Making a good cigar is about balancing the right leaves and putting them in the right order, so that the ligero is in the middle of the bunch with the milder tobaccos surrounding it, ensuring an even burn.

You can make a cigar, theoretically, out of just one plant but you won’t have complexity as far as other countries of origin, other harvest years or vintages, or other seed varieties. Leaf position is important to understanding behavior, but knowing the countries involved, the harvest year, the seed varieties involved, is important for understanding flavor.

What are the stereotypes about countries and flavors?

Sam: Tobacco from the Dominican Republic is mild-to-medium bodied. The strongest tobaccos come from Cuba and Nicaragua. But they combine to create different flavors that have nothing to do with those stereotypes. You shouldn’t always make purchasing decisions based on countries; a good cigar will draw on different places.

How good are Cuban cigars?

Sam: To me, it’s a myth. What people can’t get their hands on, they always say is better. I’ve had Cubans. They’re all right. I can smoke them.

Michael: One thing that makes Cubans unique is that they’re 100 percent Cuban tobacco. The available spectrum of flavor is limited by this. Cuba perfected the idea of premium cigars, blending, thinking about harvest years and seed varieties. Then they marketed it appropriately, so it became the benchmark. But if you go outside of the U.S., the U.K. for example, they’re buying up Dominican, Nicaraguan—just like the average American buys up Cubans when they’re abroad.

What should you smoke if you’re new to cigars?

Sam: Start off with something light. You don’t need nothing big. The Nat Sherman Vanderbilt [half-corona] is the perfect size. You need to test your palate out. Stay on the milder level for a couple cigars, see if you like that feel, that taste. From there you can expand up, or stay where you are.

What’s the proper way to cut a cigar?

Michael: To cut, I typically use a scissor-style tool, also called the guillotine. The line that rings the end of a cigar is the cap. The wrapper leaf is all one whole leaf that runs to the end. The cap is holding that leaf on, like the belt holding your pants up. When you cut below the lines, you cut off everything that’s holding the cigar together.

Sam: Then it’ll start to unravel on you. The pants fall down. So you just cut the tip off the top, above the belt.

Michael: A cigar is rolled foot to cap. You’re cutting at or above the horizontal lines [the belt]. If we cut below the belt, that’s a problem.

How do you properly light a cigar?

Sam: I’ll burn the end of the cigar, rotating it. This is called toasting.

Michael: A cigar can light by heat alone, without you drawing on it. By toasting, you ensure an even burn. Also, toasting—lighting without you drawing—keeps the smoke cooler, which is easier on you and makes for a more pleasant smoking experience.

How do you talk about what you’re experiencing?

Sam: Let the smoke roll around on your palate.

Michael: When you draw, it’s a cheek function, not a lung function. If you allow the smoke to hang a bit before you exhale, your palate starts to receive the stimulation of the smoke differently. It’s important to pay attention to flavors then. You have the flavor of the smoke itself while it’s in your mouth, and then you have the flavor that remains after you’ve expelled the smoke. That’s the finish. The other thing to pay attention to is the behavior—what it does to your mouth. Do you feel it in the front of your mouth? Do you feel it along the sides? Does it dry your mouth? Do you salivate more?

Wine tastes like wine. A cigar tastes like a cigar. It tastes like burning tobacco. What you want to be able to do is talk about the difference between cigars. What makes this one different from that one. The only way to do that is to find the flavors that are reminiscent of what you’ve got there.

You can talk about strength—is it mild, medium, or strong? You can talk about body—is it heavy in your mouth or light? Does it feel silky when it hits your palate? Does it feel creamy? Does it feel velvety? These are the things to think about as you visit your local cigar shop.