Derek Webb: I wore a dress to the Dove Awards to 'surrender' privilege as 'straight white man'

Drag performer Matthew Blake (left) and CCM singer Derek Webb wear makeup and women's clothing while standing in front of a cross for a music video.
Drag performer Matthew Blake (left) and CCM singer Derek Webb wear makeup and women's clothing while standing in front of a cross for a music video. | Screenshot:YouTube/DerekWebb

A part-time Christian contemporary music artist is defending his decision to wear a dress to the Dove Awards in an effort to “surrender” his privilege of being a “straight white man.”

Derek Webb, the lead singer for Caedmon’s Call, shared a short video Thursday on social media in which he offered more insight into why he wore women’s clothing to the popular Christian music award show.

“Why did I wear a dress to the Dove Awards?” Webb asked. “As a cis, straight white man, I walk into a room like that, and any room, with an incredible amount of advantage and privilege.

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“If I'm attending as an ally of friends and colleagues, I should do everything possible to surrender that privilege at the door. If the way you look at my loved ones isn't the way you look at me, I'm not truly standing with them.”

Visibly wearing dark nail polish, Webb cited a quote by LGBT-affirming pastor Stan Mitchell, saying, "If you claim to be someone's ally but aren't getting hit by the stones thrown at them, you aren't standing close enough."

“Plus,” he added, “I have amazing legs.”

One of the responses to Webb’s tweet criticized him for appropriating “gender”: “My gender is not your costume. You have chosen sides and abandoned and disrespected women. This will not be forgotten. You are no one’s ally when you bring more stones into their lives. Btw that dress could have been cute but you did it dirty.”

Another X user quotedDeuteronomy 22:5: “A woman must not wear men’s clothing, nor a man wear women’s clothing, for the Lord your God detests anyone who does this.”

Webb, who is no stranger to the Dove Awards, with 10 nominations and three wins, also said this year would be the first time he attended the event in person.

The controversy began after Webb shared an image of himself on Oct. 17 wearing a woman’s dress, pearls and black stockings with the caption, “despite having won a few over the past 20+ years, tonight will be my first ever trip to the dove awards, in the company of some very good friends (@FlamyGrant and @gracebaldridge, among others). i hardly ever dress up, but this feels like a very special occasion.”

A short time later, he tweeted another image of himself along with Matthew Blake, a former worship leader who wears makeup and women’s clothing and performs under the name Flamy Grant, and Grace Baldridge, who performs as “Semler.”

Webb's ex-wife, artist Sandra McCracken, was nominated at this year's Dove Awards for her album Light in the Canyon. In 2014, Webb and McCracken divorced after 13 years of marriage after he admitted to an extramarital affair. The duo have two children together.

While Webb attributed his wardrobe to the “special occasion” of the Dove Awards, the “Jesus Hypothesis” singer hasn’t shied away from wearing women’s clothing on multiple occasions in recent months. 

On the same day as the Dove Awards photos, he posted another image of himself in the same dress in an anniversary message to his wife, Abbie Parker.

Ian M. Giatti is a reporter for The Christian Post and the author of BACKWARDS DAD: a children's book for grownups. He can be reached at:

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