Traditional tattooing has always been an expression of freedom and wanderlust, with many of the most popular images representing the voyages sailors accomplished during World War II. Today, that message still stands and this style has migrated from the United States to artists around the globe. Pennyboy got his start tattooing in Milan, Italy, and was quickly seduced by traditional tattooing. It’s since become his specialty and now he’s putting his own spin on Americana’s signature tattoos.

Take us through your upbringing in Italy and how you became interested in art.

I fell in love with art when I was 16 when I saw a documentary about classicism with my mum. Since then, I haven’t stopped drawing. Moving to Liverpool, England, was a game-changing moment thanks to the lessons I learned and the people I met.

How were you introduced to tattooing and what was your first tattoo experience like?

I got introduced to the world of tattooing through my brother who’s covered in tattoos, and I started going with him to his appointments. In the beginning the artists wouldn’t let me watch, but day after day I started seeing more and more. After that, I took a course in Rome and started my apprenticeship at Street Tattoo Studio in Milan.

My first tattoo experience was horrible. I wasn’t nervous but the truth is, I had no idea what I was doing. This motivated me to improve and keep getting better.

Did you have an apprenticeship and what was that experience like?

I had the old style of apprenticeship. I had to work hard and worry about all the crap no one wanted to know about. I had to build my own tattoo machines and clean the studio at the end of the day, but also keep drawing 24/7. I also had two other jobs initially because I couldn’t pay my expenses with tattooing

What’s your favorite style to tattoo in and why?

Traditional is my favorite because it allows me to express myself completely and it gives me access to a variety of artistic options.

What’s your favorite part about traditional tattooing?

I like that traditional has a selection of rules, such as groovy lines, defined colors and heavy blacks.

Do you break any of the rules of traditional?

The one rule I don’t follow in traditional tattooing is putting bold lines next to super thin ones. I like using this technique because it helps to create contrast thanks to the little details.  

How do you think traditional tattoos have evolved over time?

With time, traditional tattooing has reached a really high standard in quality. This is because of the evolving materials we use today and the influences taken from artists around the world who have put their own flair into this style, creating an artistic melting pot.

You’ve tattooed many tricky body parts: throats, palms, sternums, etc. Which part of the body is the most difficult to tattoo and why?

I have tattooed every single part of a body in my career, and in my opinion the most difficult parts to tattoo are the palms, neck, ribs and eyelids.

What advice would you give to your younger self about tattooing?

My advice to my younger self would be to start traveling around the world earlier. Traveling has changed the way I see the world and my job.

What’s something you wish you knew about tattooing before you started?

I really wouldn’t want to know anything about tattooing before I started because my career has been a continuous journey. Knowing something before you’ve even experienced it takes away the whole meaning of it.