Penny Skateboards: The Brand’s Roots

Penny Skateboards has its roots in the history of plastic skateboards, a segment that emerged many years before the Australian brand’s global explosion.

The first plastic skateboards were actually created by Larry Stevenson, a legendary surfer and lifeguard from Venice Beach, who founded the Makaha brand, introducing a concept that was completely different from the classic wooden boards of the time.

Over the years, other major skateboarding brands such as Globe, Krooked, and Stereo also began experimenting with small plastic cruisers, but the true modern revolution came in 2010 when Ben Mackay officially founded Penny Skateboards. The name Penny comes directly from the founder’s sister, named Penny, and remains one of the most iconic elements of the brand’s identity to this day.

The idea of creating compact, lightweight, and fun mini cruiser boards has been with Ben Mackay practically since childhood. At the age of 5, his father gave him his first plastic skateboard, bought at a department store, and from that moment on, he developed a true obsession with this type of board.

As he grew up, Ben began building small handmade prototypes that he sold to local skate shops near his home, personally handling both the design and production.

Thanks in part to the sales techniques taught by his father, he managed from a very young age to turn that passion into something tangible.

Ben Mackay was constantly experimenting with new materials as alternatives to classic Canadian maple, working with fiberglass, carbon fiber, and various plastic blends in an effort to create a cruiser that was more durable, flexible, and high-performing than traditional models.

Penny Skateboards is here to stay

Today, the construction method used by Penny Skateboards is considered one of the most robust and reliable in the world of plastic cruisers. Over the years, the Australian brand has perfected a special composition that offers flexibility, strength, and durability all at once. This is one of the main reasons why Penny boards continue to be so popular with both beginners and more experienced skaters.

The top of the board also features the famous “Waffle Top” structure, a raised textured surface designed to provide grip even without traditional griptape. This unique design significantly improves board control and allows you to keep your foot stable even during fast carving or on slightly uneven surfaces.

Penny Skateboards are available in a huge variety of colors, graphics, and exclusive designs. Over the years, the brand has built much of its success on the customization and highly recognizable aesthetics of its cruisers. Customers can choose minimalist setups, vintage colorways, or more unique and limited-edition artistic collaborations.

One of Penny’s greatest strengths has always been its practicality. A Penny Skateboard is lightweight, compact, easy to carry, and perfect for everyday use. You can put it in your backpack, leave it in the car, or take it on vacation without any hassle. This is precisely why Penny cruisers have become extremely popular during the summer, especially in beach towns or cities where you can easily move between skate parks, boardwalks, and bike paths.

Over time, Penny Skateboards has collaborated with famous artists and brands such as Andy Davis, Star Wars, Burger Records, and Tyler Sprangler, creating special collections that have helped make the brand even more iconic on the international cruiser scene.

Penny Skate: Trucks, Wheels, and Bearings

A key part of a Penny Skateboard’s performance comes directly from the trucks. Penny uses high-quality cast aluminum trucks, designed to offer an extremely smooth feel while riding. They are very durable, yet at the same time allow for quick turns, smooth carving, and great maneuverability, especially in tight urban spaces.

Depending on the kingpin adjustment, the board’s handling changes significantly. A softer setup makes the cruiser very surfy and fun, while a stiffer adjustment increases stability and control at higher speeds. This makes Penny cruisers extremely versatile for different types of use.

The wheels also use top-quality urethane. On the classic 22” and 27” models, you’ll generally find 59mm wheels, while on longboard models the size increases further to improve comfort and speed. Each size is designed to perfectly suit the type of board and the terrain it will be used on.

With a hardness of 83A, Penny wheels are soft, smooth, and perfect for handling rough surfaces, uneven asphalt, and bumpy pavement without sacrificing too much comfort. This is one of the reasons Penny skateboards are so enjoyable to ride in the city compared to a traditional street skateboard.

Penny Skateboards: Speed, Control, and a Unique Feel

The Swirl bearings mounted on Penny Skateboards are strictly high-quality ABEC 7 and guarantee excellent speed and smoothness. Despite the board’s compact size, a Penny cruiser manages to be extremely fast and fun to ride, especially once you’ve mastered good pumping and carving techniques.

Many people think a Penny is easy to use simply because it’s small, but in reality, it still requires balance, control, and a bit of practice. It’s precisely this combination of compactness, speed, and responsiveness that makes riding extremely fun for both kids and adults.

The Penny Skateboards range now covers a wide variety of sizes. It starts with the classic 22-inch model and extends to longer cruisers and 36-inch pintail longboards. Each configuration offers a different feel underfoot and allows you to tailor the setup to your preferred riding style.

Penny Surf Skate and Waterborne System

In recent years, Penny Skateboards has further expanded its lineup by introducing versions compatible with the renowned Waterborne system, one of the most popular technologies in the modern surf skate world.

Thanks to this special adapter mounted on the front truck, even a classic Penny cruiser can be transformed into an extremely smooth and responsive board, capable of replicating sensations very close to those of wave surfing.

The Waterborne system drastically increases the turning radius and makes carving much deeper than that of a standard traditional cruiser. This allows for incredibly smooth pumping, tight turns

, rapid transitions, and incredible freedom of movement even in tight spaces. This is precisely why many riders use Pennys with Waterborne setups to practice surfing out of the water or simply to achieve a more creative, smooth, and fun ride during daily cruising.

The combination of low weight, compact size, and surfy feel has made Penny Surf Skates extremely popular in recent years, especially among those looking for a board that’s easy to carry but capable of delivering a very different experience from a classic skateboard.

Penny Skateboards and Pleasures Milano

At Pleasures Milano, we curate skateboards, cruisers, and surf skates by truly living the skateboarding culture every day for over twenty-five years. We don’t choose products just by looking at catalogs or current trends, but by testing setups, wheels, trucks, and boards directly on the street, in skateparks, and during daily sessions.

And that is precisely why Penny Skateboards continues to be one of the absolute benchmarks in the world of compact cruisers.

Over the years, we’ve seen thousands of people get into skateboarding thanks to Penny: boards that are easy to use, lightweight to carry, and capable of transforming any daily commute into something much smoother and more fun.

From classic models to more advanced setups featuring the Waterborne system, the Australian brand has succeeded in creating a true icon of modern cruising.

Whether you’re looking for an original Penny, a high-performance cruiser, or want to build a compact and creative surf skate setup, at Pleasures Milano you’ll find a selection curated by people who truly live and breathe skateboard and surf skate culture every day.