Is there a celebrity in need of a more serious image overhaul than Justin Bieber? Memories of the trouble-making pop star’s music (remember he’s a singer?) evaporated this year as he made headlines for arrests, court appearances and getting in fights with Orlando Bloom.

Perhaps looking to battle this bad press, Bieber showed up for a surprise appearance at CBS’s “Fashion Rocks” concert special on Tuesday night, filmed in New York City. A fine idea in theory: show up for 30 seconds, smile, introduce a performance in front of millions of viewers, get some good will from the show biz crowd. Done and done.

Bieber did that all, but unfortunately also made the unwise decision to participate in a bit where he stripped down to his boxers to promote the Calvin Klein brand. A good way to get attention, but not the greatest move for one’s dignity — as Bieber was loudly booed right before (and during the process of) taking off his clothes.

Technically, it made sense with the context within the “Fashion Rocks” show, which host Ryan Seacrest repeatedly reminded the audience was to honor the “powerful relationship between fashion and music.” As multiple artists performed (Usher, Miranda Lambert, Enrique Iglesias, Luke Bryan, Jennifer Lopez, etc.), supermodels walked around the stage to show off designer clothes.

“To introduce our next performance which features the latest looks from Calvin Klein jeans and underwear, we have two of his very close friends. Let’s hear it for supermodel Lara Stone and Justin Bieber,” Seacrest said about 90 minutes into the special.

As Stone and Bieber walked out arm in arm, the shrieks from the crowd began; and so did the jeers. Bieber tried some scripted banter over the noise. “So, uh, I actually don’t feel comfortable unless I’m in my Calvin’s so…is that cool?” he asked as the booing began.

“Go on, darling,” Stone said as Bieber quickly took off his jacket, shoes, pants and shirt until he was just in his aforementioned Calvin’s. The boos only increased. It was awkward.

“Is that better?” he asked when it was mercifully over.

“So much, thank you Justin,” Stone assured him. The duo then introduced Rita Ora’s performance.

Lesson learned, celebrities: If you want to take off your clothes on stage for a bit and try to win fans over, go right ahead. Just know that if you’re the kind of person who also gets booed in public, it’s all going to look sad and just a little too desperate.