A Roundup of Donny Osmond’s Best Fashion Moments: From Costumes to Casual Looks

In the mid-‘60s, Donny Osmond shot to fame in one of the world’s most successful family bands — The Osmonds. Years later, his solo career took off, earning him the love of millions of fans all over the world and establishing himself as an icon of the pop genre. He’s sported some memorable looks on the stage over his years in the spotlight. 

Donny has always been a risk-taker when it comes to the outfits he has rocked on tour and is never afraid to push the envelope with his performance attire. In June 2022, he shared an epic throwback photo on Twitter wearing an all-denim outfit and sporting his signature haircut. 

“Fashion has always been such a huge part of who I am!” he wrote along with the photo. “Maybe I should bring this look back, what do you think?”

As his fans weighed in with their opinions on his previous look, it became clear that Donny’s style truly shaped a generation. The “I’ll Make a Man Out of You” singer and his sister, Marie Osmond, sported some colorful costumes on their 1976 variety show, Donny & Marie. From feathered boas to neon jumpsuits and satin pants, the famous siblings proved that they were always looking to have fun and not play it safe with their style. 

In February 2019, Donny paid homage to some of his past costumes when he competed in season 1 of The Masked Singer as the Peacock. The costume was full of colorful feathers, sequins and suede design accents. 

“I have to say, The Masked Singer costume staff deserves a major shout-out for the beautiful costumes they designed and brought to life for the show,” the iconic performer reflected on Facebook in March 2019. “Not only that, but they masterfully repaired the peacock costume after every performance. Each time I decided to slide on my knees during the show, the costume team replaced all of the feathers that came off in the process.”

Donny wowed the judges with several powerful performances during the competition that led him to finish as the runner-up. 

“I left a trail of blue feathers everywhere I went,” he continued. “Let’s just say it wasn’t difficult to find the Peacock backstage.”

The “Puppy Love” crooner also shared the reason why he decided to compete as the Peacock. 

“When you get right down to it, I started my career on NBC,” the dad of five told Deseret News in March 2019. “So, there were so many subtle hints throughout this whole series, as far as who the Peacock was.”

Keep scrolling for a look back at Donny’s best fashion moments.