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Coolest Cigar Apparel

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It goes without saying that if you’re here, you love smoking premium cigars. You get to relax, taste blends crafted by some of the world’s best cigar rollers and enjoy time with friends.

But let’s not kid ourselves by pretending we don’t know we look super cool while smoking – and the best way to enhance any experience is knowing you look good doing it.

So today, we’ve put together some of our favorite cigar apparel pieces that will have you looking as cool as you feel when you spark up your next cigar.

What Counts As Cigar Apparel?

We need to preface our list by saying that so many premium cigar brands make great hats, t-shirts, jackets, koozies, and probably a lot more – but this article will not feature those. Today, we will focus on stylish staples that don’t belong to any brand or feature specific cigar-adjacent pieces that are too cool not to mention.

We won’t waste any more of your time; let’s dive into the coolest cigar apparel on the planet.


  • Michael Jordan Championship T-Shirt:
    You can’t be six-time NBA champion and MVP Michael Jordan, but you can wear this super cool shirt with his picture on it. Nothing says champion like smoking a cigar, and this t-shirt is your best bet for a casual and cool expression of your hobby that looks great and won’t break the bank.


  • Cigar Club Crew Neck:
    Look, we know Privada Cigar Club can stir up a lot of emotions in the industry, but no one can deny that their merch is incredible. Even if you’re not a member of the club, the Privada merch is stylish and comfortable. The best part? You can showcase that you’re a cigar fan without wearing one of the cheesy cigar-saying t-shirts most people associate with “cigar apparel.”


  • Bermuda Shirt:
    We’re making our way into classic cool-cigar-guy territory because just like cigars are timeless and cool, there are some pieces of apparel that you have to mention if you’re writing a blog called “Coolest Cigar Apparel on the Planet.” And when you slide on a Bermuda shirt, spark a cigar and close your eyes, you’re going to look and feel like the coolest dude around (who may or may not be on an island).


  • Panama Hat:
    Worn by a number of the industry’s top cigar experts – as well as being iconic on the island from which cigars got their roots – the “Panama” hat continues to embody that laid-back island vibe synonymous with being a cool cigar smoker. Show off your “cool” while smoking your favorite premium cigar with any Panama hat.


  • Smoking Jacket:
    Hopefully, none of you are surprised that the smoking jacket has taken the top spot for the coolest piece of cigar apparel on the planet. While the smoking jacket may bring iconic playboys to mind, it also emits an heir of importance and class no matter you’re at the lounge or smoking alone in the garage. We can personally recommend the smoking jacket linked here, but any smoking jacket that makes you feel cool and confident is the right one for you.

Find a cigar perfect for your new apparel

Now that you’re decked out to the nine’s, find a cigar that’s perfect for you.

Learn More

What’s your favorite piece of cigar apparel?

There’s a lot of it out there, but the good ones are hard to find. Comment your favorite piece so we can pick it up for ourselves!

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Comment Comment (6)

Comments

  • Member Avatar

    6 Cotto

    (2 years ago)

    I like the Panamá hat and Bermuda shirt. The get away outfit with the cigar.

  • Member Avatar

    100 Goomba

    (2 years ago)

    Cuban Cigar shirt

  • Member Avatar

    17 Service101

    (2 years ago)

    I have the hat, just not sure I'm novice enough to wear the jacket.

  • Member Avatar

    1 CigarKirk

    (2 years ago)

    Always wanted a smoking jacket! Old school cool…

  • Member Avatar

    1 dark.enigmas@gmail.com

    (2 years ago)

    I think the coolest cigar apparel is at this place. www.staysmoky.com

  • Member Avatar

    4 ghostshadow

    (2 years ago)

    For me personally, I am a T-Shirt guy. I wish more T-shirts were available at a reasonable price. Some shirts available on the market are extremely scarce and hard to come by and when you do find them they are marked up waaaay too much, especially when they're printed on crappy gildan shirts haha! Either way though, I still try to get my hands on em as much as possible!

    Also, meshback trucker hats! We need more of those! No more dad hats and weird curved brim farmer hats.

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