A suit with a blazer, but no shirt, at the Critics’ Choice Award
Is there anything more girl boss than rocking a well-tailored suit without a shirt underneath? At the 2015 Critics’ Choice Award, she showed up in a smoldering red suit selected from Dolce & Gabbana’s spring 2015 collection. The only accessory she wore with it was a chic gold body chain. Even for Aniston, who often bares her chest at public events, this was a bold look. She also brought Justin Theroux to this event, and they wed seven months later.
A risqué look at the 2017 Oscars
Aniston was giving Hollywood siren at the 2017 Oscars, where she wore a navel-plunging gown with a thigh-high split. The sparkling black dress was paired with approximately $13 million worth of Lorraine Schwartz diamonds, which included stunning 100-carat diamonds in emerald-cut earrings. Some were surprised by how blinged out Aniston was, since she told a NYT reporter in 2015 that she’s “not a diamond girl.”
Her sparkling, skin-baring Versace minidress at the 2023 Murder Mystery 2 premiere
Jennifer Aniston has spent decades proving she’s not afraid to surprise—and her 2023 Murder Mystery 2 premiere look was proof she’s still got that fearless spark. Skipping the “good girl” image entirely, she stepped onto the red carpet in a shimmering, semi-sheer metallic Versace minidress that seemed to glow under the lights. The silver mesh and delicate strips revealed just enough skin to turn heads without crossing the line, creating the illusion of a dress that showed more than it actually did.
The moment was pure Jennifer—elegant, confident, and effortlessly daring. While her look stole the show, she playfully poked fun at her co-star Adam Sandler, who arrived in a baggy New York Knicks sweatshirt, the perfect comic contrast to her high-fashion statement.
For Aniston, fashion has always been about freedom, not fitting into anyone’s box. As she once said, “Don’t let yourself become comfortable and play it safe.” Decades into her career, she continues to prove that advice true—still bold, still evolving, and still the woman who can make a red carpet light up.
