Poor Billy’s Barber Shop

06/18/2026

🌴🍧 Cool off with Tropic Style at Poor Billy’s! 🍧🌴

We’re excited to welcome Tropic Style Shaved Ice to the shop this Friday, June 19th and Saturday, June 20th from 10 AM – 5 PM!

Whether you’re stopping in for a fresh cut, exploring downtown, or just looking for a sweet way to beat the Florida heat, swing by and grab a shaved ice from one of our favorite local vendors. ☀️🌈

📍 Poor Billy’s Barber Shop
🗓 Friday & Saturday
⏰ 10 AM – 5 PM

05/22/2026

We had such an amazing time at Career Day at the elementary school today. Getting the opportunity to share what we do, talk creativity, business, and community with so many awesome kids was honestly such a rewarding experience.

Watching them light up with questions, ideas, and excitement about the future was incredibly inspiring. Huge thank you to the teachers and staff for having us, we’re grateful to be part of such a supportive community and hope we encouraged a few future creators, entrepreneurs, artists, and dreamers along the way. 💛

05/21/2026

Two great-looking cuts by two average-looking fellas.

05/04/2026

05/01/2026

It’s been about 21 years since my beard has been this short. Usually I chicken out long before this point.

Honestly, this beard has probably been the longest relationship of my life. And no, I didn’t fully shave it off… baby steps. But this was still a weirdly emotional haircut for me.

The reason I’m posting this is because I think a lot of us get way too attached to our hair or beards. Sometimes you just gotta send it. Summer’s here, get the buzz cut. Chop the beard down. Try something different. Worst case? It grows back.

Trust me, I get it. The first couple days after a big change can feel rough. Some of us are more genetically blessed than others in the beard and hair department. But if you’re rocking the patchy beard or hanging onto those last few hairs because it genuinely makes you feel confident? Slay, king!

But if you’re only keeping it because you’re scared of how you’ll look without it… cut it off. You might end up liking the fresh start more than you expected. Or like me, you’ll rock it for a little bit and go back to your default. Long beard feeling confident and unapproachable.

04/17/2026

Cowboy up, there’s a new sheriff in town.

04/15/2026

One less hippie.

04/02/2026

I had the huge honor of finally meeting a friend I’ve only known through Instagram.

When I was first getting started as a barber, there were a few shops around the world that I really looked up to, places that represented community, talent, and a deep love for the history and craft of barbering. One of those shops was (and still is)

Over the years I’ve had the chance to connect with a few incredible barbers from that shop on instagram, and one of them is . From a distance he’s been a great colleague, encouragement in the craft, and a fellow film photography nerd.

Te and his brother are on vacation and took time out of their trip to stop by the shop. We caught up, talked barbering and film, and he and his brother got some good old-fashioned head shaves.

Moments like this remind and I how small and tight-knit the traditional barbering community really is. Grateful for friendships this craft brings into our lives. 🤝

03/18/2026

Join us for the Poor Billy’s Photo Walk!

📆 Saturday the 28th
⏰ 3 PM – 5 PM
🗺️ Poor Billy’s

We’re meeting up at the shop for an afternoon of exploring, photos, and hanging out. Whether you’re a total beginner with a smartphone or a pro with a vintage Leica, everyone is welcome!

Feeling competitive?
Enter our COLOR HUNT CONTEST!
To add a little spice (and help with those “what do I take a photo of?” nerves), we’re hosting a scavenger hunt.

• How it works: We’ll give you a specific color. As we walk, keep your eyes peeled for that hue and snap a photo.
• The Goal: Collect your 9 best shots featuring that color.
• The Prize: Poor Billy’s will vote on the best grouping. The winner walks away with a free roll of Kodak Gold 200 and free development from our friends

Grab your gear and we’ll see you Saturday the 28th!

03/10/2026

At Poor Billy’s, we believe you make your own luck.

But if you feel like you need a little green for Saint Paddy’s Day, we’ve got you covered. We’re dropping a very limited run of our “Gentlemen Make Their Own Luck” Kelly Green T-shirts.

Grab one while supplies last. (Very limited, sizing and supply.)

More importantly — book your appointment in advance. Don’t wait around hoping for a lucky opening.

And for those of you who like to test your luck…
join the waitlist and roll the dice.