Tony Awards 2025 Style File: MAYBE HAPPY ENDING Star Darren Criss

Posted on June 09, 2025

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Maybe Happy Ending star Darren Criss picked up his very first Tony award, for Lead Actor in a Musical, and he opted to indulge in his cultural queerness by picking two sassy outfits for the evening.

 

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Hunh. We can’t quite get a handle on this one. The style works for him, but the proportions seem off. The oversized lapels work with the flared pants, but not with the short length of the jacket. This looks like crystal beaded velvet, which sounds fantastic on paper, but it seems too heavy and winter-appropriate. Plus the pattern is kind of dreary and looks like upholstery. It’s really not working for us, although we appreciate the attempt.

 

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This is fantastic. The proportions work really well and we like the cropped jacket with the huge pants. Our only quibble is with the shoe choice. It’s giving doll feet.

 

Style Credits:
First Look: Custom Christian Siriano Metallic Ombre Tuxedo Jacket and Trousers | Alexis Bittar Brooch | Christian Louboutin Shoes
Second Look: TBA
Styled by Ashley Weston

 

[Photo Credit: Jennifer Graylock/INSTARimages, Barbara Hine/Future Image/Cover Images, Kevin Mazur/Getty Images for Tony Awards Productions, Mike Coppola/Getty Images for Tony Awards Productions]

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