The cigar industry has such a wide, broad, and eclectic sense of fashion that I decided it deserved a deeper dive. With such variety sported by cigar smokers at every shop, bar, and cigar festival across the country, I’ve been inspired to craft the definitive guide to what your wardrobe (boiled down to the most common/popular/bizarre) says about you as a cigar smoker.

Now, this article is in no way intended to put down any person’s or brand’s fashion choices; it is merely observations on what I have seen in the wild. We are all brothers and sisters of the leaf, and I say, wear whatever you want! That being said, there seems to be repeating patterns, showing the correlation between certain looks/styles and cigar-smoking preferences… bear with me and read along for my top conclusions.

Jackin’ Around is a fringe column that looks at the cigar industry under a much different light… one may even say the light has long since gone out.
Golf Guy

You are super tan and have a polo shirt tucked into khaki shorts. You are always either just getting done golfing or just headed to the golf course. Everyone knows your handicap (even the people who don’t know what that means). You are a shop regular but you don’t stay long. You smoke Alec Bradley and Ashton.

Suit Guy

You’re wearing a brand new, freshly pressed suit, along with a fat watch and a pair of shoes that look like they cost more than my car. You’re constantly traveling or on your cell phone closing deals. You have a closely cropped beard and smoke Davidoff and Nat Sherman.

Guyabera Guy

You are a pretty standard cigar smoker. You probably have a local B&M where everyone knows your name and you could talk about any of these topics for hours: guns, booze, cars, and sports. You live in Miami and smoke the classics: Montecristo, Macanudo, H. Upmann.

Cigar Guyabera Guy

Fedora Guy

You probably own a guayabera. You’re also a little more hip than the standard cigar smoker; maybe you jam a little Dave Matthews Band every once in a while. Your main pairing is coffee. You smoke Rocky Patel and Perdomo.

Tattoo Guy

You are on the edgy side of the cigar scene. You might own a motorcycle and be the biker gang type, or be of the hip, artsy persuasion. The tattoo guy has now become a staple of the cigar industry, thanks to pioneers like Pete Johnson, James Brown, and Matt “Boofy” Booth. You smoke Tatuaje, Black Label Trading Co., and Room101 and are probably a member of the SNS community.

Cool Hat Guy

You are A.J. Fernández. You smoke A.J. Fernández.

A.J. Fernández hat

Beard Guy

You have a sweet beard (duh). You are probably the beer expert around the shop and know a decent amount about woodworking. You probably own a T-shirt that says “Brettanomyces” in a witty fashion. You are an expert in the realm of coffee and everything else craft. I won’t call you a hipster, but others might… You smoke Warped.

Police Uniform

There is always a guy in full uniform at my shop, and at the shop I was at before that, and the one before that… It is to the extent that I wonder if there is a secret society of officers that all agree to stand guard over our precious B&Ms. They probably all smoke Protocol.

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Goatee Guy

You play the bass guitar. I don’t know what you smoke…

Cigar goatee guy

Smoking Jacket Guy

There are two roads you can take if you are the person in the Hefner-style smoking jacket: one is the super-classy diplomat look; the other is the insane pattern-covered jacket with matching hat and slacks. The two groups couldn’t be more opposite. One group smokes mostly Cuban cigars; the other smokes mostly infused cigars. I will let you decide which is which.

Kilt Guy

You wear your Scottish pride on full display at events. Maybe you aren’t even Scottish; maybe most definitely you aren’t wearing underwear… This guy is usually one of the drunker people at any cigar festivity, but what can I say, any man bold enough to rock commando in public is likely to be a party starter. You fumble at least three cigars per event. You smoke whatever you are handed.

Jean Jacket Guy

You have no less than five rings on your fingers. You jam to hip hop and rock some very eclectic clothing. You are wearing one hat minimum and three hats maximum. Bonus points if you have a Liga tattoo. Double bonus points if you got it on Safari. You smoke nothing but Drew Estate baby (#DE4L).

Jean jacket cigar guy

Too-far-Buttoned-Down-Shirt Guy

Your hair is slicked back; you drive a nice car. You don’t necessarily own a boat, but you have a buddy that owns a boat. You may not own an oversized reptile, but you’ve certainly contemplated the purchase—ultimately kicking the idea down the road after working out the logistics. You smoke La Barba, Caldwell, and Tommy Bahama.

Dojo Merch Guy

You are the top of the food chain baby—the peak of cigar fashion. People want to be you; you have to bat away the opposite gender with a stick. When you walk into a room or an event, everyone stares at you with envy. You smoke whatever’s the most fun and won’t think twice about supporting those that are genuine and/or altruistic. But most importantly, you NEVER SMOKE ALONE!

Tramp Stamp Guy

You probably got it on vacation. Everyone thinks you are super cool because of it. No one ever questions your decision making. You smoke Camacho.

Tramp stamp tattoo cigar guy

You and I both know there are a host of other clichéd “cigar wardrobe guys” lurking out there. Chime in and let us know your observations in the comments below!
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