Dutton Ranch Star Annette Bening's Full Beauty Evolution In Photos

Actor Annette Bening's beauty evolution is a sight to behold because the "Dutton Ranch" and "American Beauty" star hasn't been afraid to change her look and experiment with color. "You know, glamour is really fun. Getting all dressed up and putting on fancy clothes," she shared on "Live with Kelly and Mark" (then known as "Live with Kelly and Michael") in 2014 (via E! News). Not only is Bening a celeb who can pull off dark and light hair, but she's also a staunch advocate for a red lip and fluttery falsies who's proven the importance of picking and choosing trends to follow for the most flattering aesthetic. In fact, her beauty is held in such high regard that she was awarded the Makeup Artists and Hair Stylists Guild's Distinguished Artisan Award in 2024, and she inspired the lipstick shade Annette from her longtime makeup artist Julie Hewitt's line.

But just because Bening likes to dial up the glam on the red carpet, don't be fooled into thinking she's against aging naturally. Speaking to Closer in 2023, she denied undergoing plastic surgery or invasive cosmetic procedures. "Am I thrilled every time I see my wrinkles? No. But the choice I've made is not to do any of that. It's just me. That's my approach," she said (via FemaleFirst). Her dedication to being a celeb who's confronting aging with confidence while proving beauty has no age limit is obvious throughout her transformation.

Annette Bening had started to make a name for herself in 1991 as an Oscar nominee for "The Grifters." The rising movie star, who began working with her longtime makeup artist Julie Hewitt on the project, had a distinctly vintage movie star look to match her career — with an '80s twist. At the 1991 Oscars, she wore bold red lipstick with a vintage, short curly 'do that was likely created using curlers. But she added a distinctly more modern (for the time) twist by ditching the sharp, elongated eyeliner many movie stars in the '50s paired with their bold lip. Instead, she carried the '80s trend of orange eye shadow into another decade. She clearly hadn't (yet) bowed to another divisive emerging '90s trend, though. The decade was all about superthin eyebrows, but Bening's were still full and fluffy.

At the Golden Globes that year, she proved she was picking and choosing between the '90s biggest trends. Instead of siren red lipstick, she wore a shiny plum-pink shade; one of the hottest makeup colors of the decade. She kept her eye and cheek cosmetics to a minimum, opting for a glowing complexion with what appeared to be subtle brown liner around her eyes.

By the late '90s, Annette Bening had dialed back her more vibrant lip colors and experimented with more subtle hues. At the 1999 Los Angeles Film Critics Association Awards, she stunned with more understated, natural-looking makeup. Her eyes were highlighted with subtle, light shadow up to her brow bone, and her long, fluttery eyelashes were so eye-catching they could have been falsies. She also fully embraced one of the '90s biggest makeup trends — matte skin. But, in contrast to the bronzer trend that was everywhere at the time, she wasn't afraid to embrace her fair complexion. That proved Bening didn't blindly follow trends she didn't like. 

That look was more on the subtle side, but she wasn't afraid to amp things up when the occasion called for it. At that year's Golden Globes, she sported a similar matte complexion but tried more handpicked '90s trends that served her. That included pastel eyeshadow (she appeared to wear a subtle take on the '90s staple blue shade on her lids) and another trendy plum lipstick shade. She'd also succumbed to the thin brows of the era (a '90s trend that can stay in the past), as hers seemed to be less thick and fluffy and more angular than eight years prior.

Annette Bening turned 46 in 2004 and proved there's no age limit on experimenting with beauty. Her makeup took a walk on the orange side at the "Being Julia" opening night pre-party, where she opted for a monochromatic look that brought out the warmth in her complexion. She paired subtle orange eye shadow with matching orange blush (which should be in your makeup routine, by the way) and an orangey-red, glossy lipstick. Not only did the shades match each other, but they also brought out the warmth in her new hair color. She'd swapped mousy brown tresses for golden toffee blond tresses in short waves with plenty of volume.

That wasn't the only time Bening pulled off all-orange makeup that year, though. At the New York premiere of "Being Julia," she had a very similar beauty aesthetic but added a little more blush and bronzer. The warm hue again complemented her skin tone and highlighted locks for a tanner glow than we'd seen from her in previous years. Orange makeup wasn't trending at the time, so it confirmed Bening was happy to blaze her own trail and take beauty risks.

The star's almost repeating looks may have been because she wanted to spend less time in the makeup chair. By 2004, the star was a mom of four and told People she wasn't as focused on her career (and, likely, all that comes with it, like getting gussied up for the red carpet). "I'm too interested in the other things in life, like being with my kids and being with my husband," she said.

Annette Bening had truly perfected the barely-there makeup look by 2006. At a TCA HBO Network event and while attending the opening of "The Cherry Orchard," Bening proved she left all orange cosmetics in her past as she sported simple cosmetics that let her natural beauty show. That included what appeared to be light-coverage, dewy foundation, complemented by subtle bronzer and warm blush for a slight glow. She stuck to subtle eye shadow that was barely visible and had a slight smudge of pencil eyeliner under her eyes.

The actor added a little color to her lips — but it was nowhere near as eye-catching as the orange and red tones we'd seen on her in years past. Instead, she opted for a nude shade with a slight sheen at the TCA HBO Network event and a slightly pinker nude that appeared very similar to her natural lip color at the "Cherry Orchard" event. At both gatherings, she'd barely filled in her naturally fluffy brows for a soft effect — but they were clearly growing back strong following her thinner '90s look. The star experimented with a more natural look, which may have been down to the confidence she felt at the time. During a 2006 interview with Blackfilm.com, she made it clear she didn't feel she was competing with younger actors.

Though 2008 beauty was all about matte foundation, Annette Bening served as an important reminder that not every trend is for everyone. Instead of following the crowd to the matte side again after first embracing the trend in the '90s, the star, who turned 50 that year, kept things dewy and glowing. That made sense considering light-reflecting finishes can be much more flattering on dry skin, as they don't cling to dry spots and offer the skin more hydration. She had a seriously luminous finish at the American Society of Cinematographers Annual Outstanding Achievement Awards and the Crystal + Lucy Awards that year.

But that didn't mean the actor was against experimenting or trying trends that worked for her. We noticed a slight change in her less-is-more approach to eye makeup at the Crystal + Lucy Awards, as she put her own spin on a smoky eye (aka darker eye makeup, often paired with smudgy liner), which was huge at the time. Instead of going all out with her smoky eye, which wouldn't have felt authentic considering she's always preferred a bare eye look, Bening wore smudged black eyeliner on the outer corners with blended brown and shimmery shadow. That demonstrated the importance of adapting trends and techniques to make them as flattering as possible, particularly for older women.

In 2014, Annette Bening made it clear it's always possible to have fun and change things up, as she dialed up the glam before stripping it back. At "The Face of Love" premiere and a separate screening for the movie, she was all about darker red lipstick, which may have represented her becoming more mature (she was 56 at the time). The celeb who's mastered the art of a red lip added light, pearlescent eye shadow that was concentrated in the inner corners of her eyes to highlight and brighten them. Bening still sported dewy foundation that made her skin look lit from within and opted for complexion-enhancing tan blush over bright, faddish shades or heavy contouring. Contouring famously became mainstream that year after being championed by Kim Kardashian.

That same year, Bening showed that women can both love makeup and be happy and confident without it. She joined a host of stars who called out unrealistic Photoshopping by posing without retouching or makeup for Vanity Fair. Speaking about the experience on "Live with Kelly and Mark," Bening shared she wanted to be part of the shoot predominantly because she knew she was in safe hands with photographer Chuck Close. "[...] we're peeling, hopefully, layers away and showing something that's inside, hopefully, that people can relate to in a story so it's more akin to what we do a lot of the time," she said (via E! News), comparing posing sans makeup to being an actor.

Annette Bening's 2016 makeup was all about glowing skin and a drastically different look. At the French premiere of "20th Century Women" and during a "20th Century Women" press conference, she had a semi-dewy, lit-from-within, bright, and glowing aesthetic and didn't show any signs of age spots, dark circles, or blemishes. Her eye makeup was as simple and understated as it's always been, but she wasn't afraid to change things up with her lips. Though her lipstick leaned red, it was more subtle and complemented her new dirty blond pixie cut (which gave us Michelle Williams vibes), and she gave romantic, feminine vibes via her long faux lashes. The Kansas native opted for rosy pinks on her lips and cheeks that warmed her complexion in a soft, youthful way.

The more subtle approach to makeup may have been inspired by her "20th Century Women" movie role, as her character, Dorothea, wasn't all about the glitz and glam. Bening played a single mom who needs help raising her teenage son. The character wore minimal makeup and undone hair, which Bening told Yahoo! Entertainment she had no problem with. "It's very liberating. Don't get me wrong, I have vanity and I see myself. I've gotten older and those are the wrinkles and that's what it looks like. But I really want to go with it and play the age that I am," the star, who was around 58, said. "I feel like that's part of my own little mission."

We saw Annette Bening return to her beauty roots in 2018. At a New York screening of "The Seagull," her makeup and hairstyle were very similar to the aesthetic she sported decades earlier. Bening's vintage-inspired, voluminous, curly hairstyle had returned, as had her red lipstick. This time, though, she opted for a more muted shade. She also proved she wasn't afraid of dewy, luminous foundation as she proudly (as she should!) showed a few lines and wrinkles on her well-hydrated skin, giving a masterclass in the best foundation finish for more mature skin. Bening (who had reddish-brown hair) kept her eye makeup to a minimum and seemingly skipped falsies but wore subtle mascara on her upper lashes only.

A few months later, she proved she was still all about a lipstick statement. At the premiere of "Life Itself," she rocked a curly, blond crop with glamorous, bright red lipstick. She added flattering, soft brown eye shadow to her lower lash line. Not so soft, though? Her blush. Though she'd mainly opted for a light dusting of subtle blush before, this time, she wore a more obvious shade that gave her face a warm, healthy look. Peach blush, which she appeared to wear, was huge at the time and proved Bening still had her finger on the beauty pulse.

She also made it clear in 2018 she'd decided to age naturally. "When I started, [I] formulated my own aspirations as an actress. One of them was to continue acting all my life," she told NPR. "And ... I wanted to try to portray the age that I was and not get stuck in any given period of life."

In early 2023, Annette Bening made a point of amping up her makeup while becoming a celeb who embraced her naturally graying hair. At the AARP Movies for Grownups Awards, she had lighter strands on either side of her face next to her darker, short locks. But she showed that aging and leaning into gray locks doesn't mean cutting back on makeup. She sported sophisticated, dark red lipstick, which she paired with long, fluttery faux eyelashes, semimatte foundation, and warm blush. The following month, though, she showed she (or her makeup artist) knew exactly how to switch up her cosmetics to accommodate her hair changes. At the Social Impact Fund 10-Year Celebration, her graying locks had been replaced with blonder tresses and she'd swapped her vibrant lip color for shiny coral that looked softer against her lighter hair. She also appeared to wear foundation with a slightly warmer undertone and warmer blush to ensure her golden blond locks didn't wash her out.

While Bening clearly still had a passion for hair and makeup, she admitted her appearance wasn't high on her priority list when she was acting. "Being on the stage is very liberating. You're not ever thinking about how you look; you don't have to. If anything, it's better for your performance if your mind is off that because then you can imagine being someone who's very different to you," she told The Guardian. She also opened up to PBS about the hyperfocus on her looks as a celebrity, making it clear she didn't put that much importance on her appearance. "It's an interesting part of the job," she said.

Annette Bening made it clear in 2026 that she wouldn't be putting her red lipstick to bed as her 70s neared. At the New York premiere of "The Brides," she stunned in a bright red shade that was as bold as her confidence and proved there's no age limit on pulling off a vibrant hue. To let her lips do all the talking (literally and figuratively), she paired the eye-catching shade with subtle blush and understated eye makeup, which kept her makeup from looking overdone. She left extra-large falsies at home and seemingly opted for multiple coats of black mascara to define her eyes instead.

That same year at the Lambda Legal National Liberty Awards, she showed another way to rock a colorful lip that served as inspiration for those looking for something a little softer. That time, she opted for a gentler, deep pink with softer lip liner. The hue complemented her highlighted brunette locks as she gave another hint at her gray hair, and she proved dewy foundation and long lashes had become part of her signature look that wouldn't be going away anytime soon.