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.