Don Lemon Mocks Kevin O'Leary's Fashion in West Hollywood Encounter

Former CNN anchor criticized 'Shark Tank' star's flamboyant jacket outside popular restaurant

Published on Mar. 4, 2026

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Fired former CNN anchor Don Lemon took a dig at 'Shark Tank' star Kevin O'Leary's fashion choices during a recent encounter at a West Hollywood hot spot. Lemon yelled from a car window that O'Leary's patterned jacket, which featured a fluffy padded collar and cuffs, was 'gayer than me.' O'Leary shot back that it was 'an endorsement' and called himself a 'fashionista.'

Why it matters

The exchange between the two public figures highlights the ongoing tensions and divisiveness in the media landscape, with Lemon's comments seen by some as inappropriate and insensitive. It also reflects the broader cultural debates around fashion, masculinity, and LGBTQ+ representation.

The details

The incident occurred outside the popular West Hollywood restaurant Craig's, where Lemon was captured on video yelling at O'Leary from a car window. Lemon criticized the 'Shark Tank' star's patterned jacket, which featured a fluffy padded collar and cuffs, saying 'Kevin — that coat is gayer than me.' O'Leary responded by saying 'Thank you, it's an endorsement. I'm a fashionista.' Lemon then quickly drove away, offering his goodbyes to O'Leary.

  • The incident occurred on March 3, 2026 outside the Craig's restaurant in West Hollywood.

The players

Don Lemon

Fired former anchor of CNN, known for his outspoken and sometimes controversial commentary.

Kevin O'Leary

Canadian businessman and television personality, best known as 'Mr. Wonderful' on the reality show 'Shark Tank.'

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What they’re saying

“Kevin — that coat is gayer than me”

— Don Lemon, Former CNN anchor (TMZ)

“Thank you, it's an endorsement. I'm a fashionista.”

— Kevin O'Leary, 'Shark Tank' star (TMZ)

The takeaway

This incident highlights the ongoing tensions and divisiveness in the media landscape, with Lemon's comments seen by some as inappropriate and insensitive. It also reflects the broader cultural debates around fashion, masculinity, and LGBTQ+ representation in the public sphere.