Core Insights - The 77th Primetime Emmy Awards highlighted a significant shift in menswear, showcasing a trend where men are embracing bolder and more personalized fashion choices on the red carpet [2][9] Group 1: Notable Winners and Styles - Tramell Tillman made history as the first Black man to win the Emmy for Outstanding Supporting Actor in a Drama Series, wearing an all-white double-breasted tuxedo by Dolce & Gabbana, which balanced contemporary style with classical tailoring [4] - Pedro Pascal's modern double-breasted Celine look featured slimmer trousers and long cuffs, reflecting a playful and risk-taking approach to menswear [5] - Alan Cumming's outfit from Tanner Fletcher included elements like a pussybow, demonstrating a genderless approach to fashion that expands the definition of menswear [6] - Colman Domingo's bold look at the Emmys included flared trousers and an embellished jacket, showcasing his ability to wear striking styles without being overwhelmed by them [7] - Noah Wyle's classic navy tuxedo, styled by Figs, was designed for comfort akin to scrubs, merging practicality with elegance for his first Emmy win [8] Group 2: Trends in Menswear - The 2025 Emmys illustrated that men are increasingly willing to take fashion risks, moving away from predictable styles to embrace daring cuts and playful details [9]