Annette Bening’s Best and Most Confident Looks Through the Years

As a true 20th century woman, Annette Bening is a force to be reckoned with. With a charm and acute sense of self that extends beyond the silver screen and four Oscar nominations on her resume, Bening is a staple on the red carpet season after season. While she has more than proven that she knows how to work a form fitting cocktail dress and a ball gown on the carpet, the actress is better known for her unique ability to wear menswear-inspired suits and blazers no matter the occasion. Bening’s off-duty is also not one to ignore; she possesses a cool and effortless magnetism that will inspire you to throw a cool, understated leather jacket over any ensemble. There is no doubt that her particular brand of stylish draw stems from truly authentic confidence. Click through to see the actress’s complete style evolution, from casual denim to custom gowns.


Annette Bening attends the 48th Annual Golden Globe Awards Rehearsals at the Beverly Hilton Hotel in Beverly Hills, California in1991.


Bening goes simple in black, with husband Warren Beatty at the 53rd Annual Golden Globe Awards in 1996.


A rare sequined moment at the 71st Annual Academy Awards in 1991.


Bening covers up during A.C.T.’s ‘Starry Starry Night 2002.’


Embracing a tuxedo look during the 13th Annual Premiere Women in Hollywood at Beverly Hills Hotel & Bungalows in 2006.


Bening arrives at the Los Angeles Premiere of The Women in 2008 in a sleek, red sheath.


Annette Bening in off-duty denim and white tennis shoes at the Thibiant salon in Beverly Hills, California, in 2009.


Bening attends the Mother and Child premiere at the Paris Theatre in a take on the three-piece suit,


Bening arrives at the 16th Annual Critics’ Choice Movie Awards in 2011 wearing an embellished yellow gown.


Bening poses in the press room at the 68th Annual Golden Globe Awards held at the Beverly Hilton Hotel in Beverly Hills, California. 2011.


A golden moment for Bening as she arrives at the 17th Annual Screen Actors Guild Awards in 2011.


And a silver one at the 83rd Annual Academy Awards held at the Kodak Theatre in Los Angeles the same year.


Bening stunned in a one-shouldered white gown at the 2011 BAFTA’s in London.


Bening arrives suited up to The Geffen Playhouse’s Annual ‘Backstage at the Geffen’ Gala at Geffen Playhouse in 2013.


Annette Bening arrives at ‘The Face of Love’ premiere during the 2013 Toronto International Film Festival at the Elgin in Toronto, Canada. 2013.


Annette Bening attends the 2013 AFI Fest Spotlight event in all black.


Annette Bening attends The Face of Love premiere in 2014 in a shimmering take on the pantsuit.


Another chic suiting outing for Bening as she arrives at the COLCOA French Film premiere of The Search in 2015.


With husband Warren Beatty attending the screening of 20th Century Women at the AFI Fest in Hollywood in 2016.


A rare pop of color for Bening at the Santa Barbara International Film Festival honoring Warren Beatty with the 11th Annual Kirk Douglas Award for Excellence in Film.


Bening keeps it casual for the 20th Century Women New York screening, wearing a tan leather moto jacket and dark denim jeans.


Another casual look, this time in all black, at the 2017 Film Independent filmmaker grant and Spirit Award nominees brunch.


A perfect red carpet moment at the 74th Annual Golden Globe Awards in 2017.