Alerts & Newsletters

By providing your information, you agree to our Terms of Use and our Privacy Policy. We use vendors that may also process your information to help provide our services. This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply.

Justin Bieber Goes Wakeboarding in (Very) See-Through White Boxer Briefs

The male equivalent of swimming in a white T-shirt.
Justin Bieber Goes Wakeboarding in See-Through White Boxer Briefs

Rather than donning swim trunks like a normal person, Justin Bieber had a little wakeboarding sesh over the weekend in nothing but a pair of white Calvin Klein boxer briefs. And, yes, they were super see-through once they got wet.

Bieber and longtime pal Ryan Good both stripped down to their skivvies in Miami over the weekend for a little fun in the sun, and though they surely could’ve obtained actual swim trunks, apparently there’s more swagger to wearing your underwear in the water. Among other roles (stylist, “big brother”), Good used to be known as Bieber’s “swagger coach.” That’s right: Justin Bieber used to have a swagger coach, who was photographed with a pink flamingo pool float around his waist, kicking it with his ex-pupil in Florida. (BTW, Good also happens to be Ashley Benson‘s boyfriend—not Bieber’s new flame, as some outlets reported.)

The “swagger coach” thing was just a joke, Good told Hollywood Life a few years ago, but he did say that he saw himself as a positive influence on Bieber when he went on the road with him. “I’m Justin’s stylist so I basically work with him to decide on what gear, etc. he wears,” he said. “I’ve worn a lot of hats on the road with him over the past few years with none being more important than big brother.” Over the weekend, perhaps they worked together to decide what underwear, etc., Bieber would wear in the water. And they went with white. Because white is see-through, and they knew it would generate attention.

Or maybe they were just shooting an off-the-cuff Calvin Klein ad. In any event, here’s a bunch of photos of Justin Bieber basically naked—enjoy.

StyleCaster Daily
Get the latest news and style intel delivered to your inbox.

By providing your information, you agree to our Terms of Use and our Privacy Policy. We use vendors that may also process your information to help provide our services. This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply.

PMC Logo
StyleCaster is a part of Penske Media Corporation. © 2026 SheMedia, LLC. All Rights Reserved.