Regular Skateboards rolls into Sherwood
New family-owned skate shop offers professional designs by local kids
SHERWOOD, Ore. — Sherwood’s cool kids have a new local skateboard shop and swag designer.
Regular Skateboards launched as an online small business in October 2025.
Alex Whitaker, architect by day and skateboard designer by night, is the owner.
“We're trying to get established as the go-to skateboard shop for Sherwood and the surrounding areas,” Whitaker said. “We currently have an online presence, but we’ll have a farmer’s market booth in the spring and hopefully a physical shop in a year or so.”
Originally from Texas, Whitaker and his wife transferred to Sherwood two years ago for her job at Nike with their two sons. His architecture company was already remote, so they made the move.
“Myself and my boys (ages 11 and 14), we all skateboard. I’ve been skateboarding since I was 10 or 11, and I taught both of them when they were really young, so we have quite the collection of skateboards already here in the garage,” Whitaker said.
Regular Skateboards is a drop-ship style company, where customers can order a design and the company will have it made and sent to them, with no warehousing inventory. They currently offer about six different skateboard designs.
“Both of my sons (and I), we come up with the designs. One of my son’s friends also designed one of the skateboards,” Whitaker said. “It’s all local artists and kids coming up with the designs, and then I make it a skateboard recipe. We’re trying to keep the kids involved and really make them a part of the company — it’s not just adults trying to be cool, it’s kids. The kids are actually involved in the production, also.”
Whitaker has an eye for aesthetics and is always trying to make the boards prettier than competitors by matching the wheels and trucks to the colors of the art.
“I noticed there were not really a lot of skateboard shops in the area,” Whitaker said. “So we just decided, we all knew how to make skateboards, we are all artists, so we do the designs. I have all the graphic design software already, so I just use that to make graphics skateboard-ready. It was pretty much a no-brainer when it came to deciding to go ahead and start the company.”
The name Regular Skateboards comes from something the family would ask for whenever they’d enter a skate shop.
“Every time we go and look for skateboards, as soon as we enter the shop, one of the first things we say is I just want a regular skateboard — I don’t want anything funky, I don’t want it to look weird, I don’t want it to look like a shark, I don’t want a longboard or a cruiser. I just want a regular skateboard,” Whitaker said. “We noticed we said that almost every time we went to a shop, so that’s how it all started.”
Whitaker said he likes doing business in Sherwood because of the close-knit community.
“When we go to the skate park at the YMCA, the little community there is awesome,” Whitaker said. “Everybody’s really nice to each other; the older kids are helping the younger kids learn tricks. I’ve never seen any fights. It’s just really good vibes, so we want to be a part of that community and help it grow through the brand.”
Whitaker said he has always been an artist, but he picked up graphic design during the 2008 economic slowdown. He said his favorite thing about running Regular Skateboards is “meeting more new people, to entrench ourselves more into the community.”
“This is a way for us to reach out to the community and feel more connected,” he said.
Regular Skateboards is also breaching the fashion world, offering sweaters, hats, and t-shirts so far.
“The initial reactions from people have been really positive,” he said. “You don’t have to be a skater to buy our product. You could buy one of our skateboards just because it looks beautiful and you want to display it as a work of art, put it up on your wall, or above the fireplace. We’re striving to be not just a company that’s geared just toward skaters; we want everybody to be able to enjoy our products.”
