A Mood. A Moment. A Cigar.
Cigar culture isn’t just about what’s in your hand—it’s about the people you meet, the stories you hear, the moments you create, and the space you give yourself to slow down. For Jessica Williams, that journey has grown into a nine-year exploration of flavor, connection, confidence, and community. In a world that can sometimes feel like it has an “in” crowd, Jessica’s approach is refreshingly simple: show up, stay curious, find what speaks to you, and enjoy the moment. We sat down with Jessica to talk cigars, rituals, women in the industry, personal favorites, and why sometimes the best vibe is simply taking a breath and lighting up.
Q: What’s your full name?
A: Jessica Williams
Q: What is your social media handle:
A: @Jaislimashes
Q: What was the moment you realized cigars were more than just a hobby for you?
A: I realized cigars were more than a hobby the day I sat back, relaxed, and felt my whole mind settle. The draw wasn’t just flavor, it was clarity. That’s when I knew this wasn’t just something I enjoyed… it was part of who I am.
Q: Do you remember the first cigar that truly impressed you? What made it unforgettable?
A: My first unforgettable cigar was the Stokk. The pipe-tobacco influence, the way all those flavors came together, and that smooth retrohale, it caught me off guard in the best way. It wasn’t just good… it was memorable.
Q: The cigar world has historically been male-dominated. What has your experience been like carving out your own space in the industry?
A: Honestly, it’s been smooth. The attention comes naturally, people love seeing a woman enjoy cigars with real appreciation. It always leads to conversation: how long I’ve been smoking, what I like, and the fun differences and similarities between women’s cigar preferences and men’s. That’s where the real connection happens.
Q: If you had one cigar and one dram to enjoy tonight, what would you choose and why?
A: If I had one cigar and one drink tonight, I’d reach for a Gurkha V paired with Basil Hayden Toast. The Gurkha V gives me that rich, steady flavor I can settle into, and the Toast brings a warm, subtle sweetness that complements it perfectly. Together, they create the kind of slow, calm moment I look forward to, the kind you don’t rush, you just enjoy.
Q: What is something about the cigar industry that most people would be surprised to learn?
A: Something most people would be surprised to learn about the cigar industry is how complex and layered the flavor profiles really are. Every cigar is different, none of them smoke the same. Some start subtle, then reveal hidden notes at the midpoint, and those flavors get bolder and richer as you work your way toward the finale. It’s almost like the cigar tells a story in chapters, and you don’t know the plot twist until you’re deep into the experience.
Q: What does the ritual of lighting a cigar mean to you personally?
A: The ritual of lighting a cigar, for me, is exactly what I say: A Mood. A Moment. A Cigar. It’s the pause before the world gets loud again. It’s the calm settling in, the presence returning, and that perfect stick in hand that turns an ordinary day into something better. Lighting up is the reset, the moment I choose myself.
Q: How do you think women are changing or influencing cigar culture today?
A:Women are influencing cigar culture by showing up with purpose. We’re not smoking because it’s a trend or because we want to be around men, we’re learning the art, enjoying the moment, and finding other women along the way who share the same calm, the same curiosity, and the same appreciation for a good stick. Those connections turn into bonds that are unmatched.
Cigar culture invites you in, lets you sit for a while, breathe, and enjoy the calming moment and the inviting smells. Women are expanding that space, making it more welcoming, more balanced, and more communal.
Q: If you could share a cigar with any person in history, who would it be and what would you smoke together?
A: If I could share a cigar with anyone in history, it would be Maya Angelou, my inspiration, the quiet voice that sits in the back of my mind. Her poems create steady streams of calm, and her presence alone would make the moment unforgettable. With her, I’d smoke a Definition Gen 413. Definition’s slogan, “Value the time to truly define who you are,” fits perfectly with everything she stood for. The Gen 413 represents the new, the past, and the present beginnings, exactly the kind of reflection a conversation with Maya would bring.
Q: Is there a cigar brand or blend you think deserves far more recognition?
A:*Right now, there isn’t one cigar brand I feel deserves more recognition, mainly because I’m still exploring. This has been a nine-year journey for me, and along the way I’ve tried quite a few sticks, but I’m still in that learning and understanding phase. I don’t smoke one brand daily; I move through a variety that hits my palette in different ways.
Gurkha, My Father, and Don Pepin have caught my attention more than most, but I’m still growing, still discovering, still figuring out what speaks to me. And that’s the beauty of it, the journey isn’t finished.
Q: For women curious about cigars but intimidated to try, what advice would you give them?
A: For any woman curious about cigars but intimidated to try, my advice is simple: don’t be. We walk into a room and we own it, bring that same mindset with you. And if you’re unsure, ask. This culture is built on teaching, showing, and sharing.
When you sit in that room and ask, “What should I smoke?” or “How do I do this?” we light up with a smile because we’re happy to guide you. There’s no gatekeeping here. Women in cigar culture share the passion, the knowledge, and the moment. You’re invited to sit, breathe, and enjoy the calm right along with us.
Q: Have you ever felt that being a woman in the cigar world changes how people perceive your palate or expertise — and has that ever worked to your advantage?
A: Absolutely, being a woman in the cigar world definitely changes how people perceive your palate at first. They automatically assume I want a sweet tip or something light. But the moment I say what my go-tos are, everything changes. They light up, get excited, and start sharing their favorite blends.
I always laugh when they say, “Oh, you smoke the strong stuff?” Strong? No. Full body. Bold. Nutty. Peppery. Absolutely.
And the best part is the exchange. They hand me cigars, “This is my favorite, you should try it.” Then I reach into my bag, hand one back, and when they see my selection, it creates an instant bond. After that, every time I walk in, they’re ready to share, talk, and enjoy cigars together.
That’s the advantage, the connection, the respect, and the shared passion that grows from surprising people in the best way.
Q: Is there a cigar you love that most ‘purists’ would secretly judge you for — and why do you enjoy it anyway?
A: No, there isn’t a cigar I love that purists would judge me for. My favorite is the Gurkha V, and since you can no longer purchase it, my second go-to is My Father Blue. Both are great cigars, easy, calm, reliable sticks that fit my mood every time. I enjoy them because they bring me peace, not because they fit anyone’s idea of what a “purist” should smoke. My palette is mine, and these cigars speak to it.
Conclusion
At the end of the day, Jessica’s story is a reminder that you don’t have to fit someone else’s definition of what belongs in the cigar world. You can be curious, try something new, change your mind, find your favorites, and make the experience your own. Whether you’re nine years into the journey or still wondering what the heck you’re supposed to order, there’s room to learn and connect. Because sometimes it really is that simple: A Mood. A Moment. A Cigar.
