A Look Back at Meg Ryan's Most Stylish Moments

See some of the most iconic outfits worn by the Hollywood mainstay throughout her career

Throughout her career, Meg Ryan has provided some unmatched wardrobe inspiration. From her red carpet looks to her on-set style, the Hollywood mainstay always showed off her high-fashion tastes no matter the occasion.

From her A-list debut in the '80s to her new-millennium looks, check out photos of some of Ryan's most iconic outfits from way back when.

In Season

Some of Ryan's most iconic looks came in the 1989 classic When Harry Met Sally. Her style in the film will go down in history as the pinnacle of 1980s fashion — especially fall fashion!

Sweater Weather

Talk about chunky sweater perfection.

A Royal Encounter

While celebrating the 1989 premiere of When Harry Met Sally in London, Ryan and Billy Crystal were joined by a very special guest: Princess Diana. For the occasion, Ryan opted for a brown velvet off-the-shoulder gown, while the Princess of Wales stunned in a red and gold number.

Stylish On Set

Ryan twinned with her equally stylish leading man, Tom Hanks, as the two rocked khaki pants on the set of their 1998 rom-com, You've Got Mail. It's no wonder they made a perfect match on the big screen!

Chic Upon Arrival

Ryan flashed her signature smile as she hopped out of a car at the 1988 IFP/West Independent Spirit Awards in an adorable, very '80s, grey dress which she paired with a spunky set of shades.

Bright Smile

The rom-com queen layered up in a gray blazer and paisley scarf as she supported the stars of Cross Your Heart at their film's premiere in 1987.

Coolest Couple

The A-list actress joined her then-husband, Dennis Quaid, for a red carpet date night at the L.A. premiere of his flick Great Balls of Fire in 1989. Ryan showed off a more grunge side in a leather jacket. Her signature blonde locs were cut into a face-framing bang that completed her edgy ensemble.

Shades On

Ryan was the picture of chic at the 1993 ShoWest movie convention in Las Vegas. The superstar wore her hair in a shaggy bob and accessorized with round, arched sunglasses. Her striped top and long-hemmed blazer were both smart and style-savvy.

Color Coordination

And as she stepped into the new millennium, Ryan brought her sense of style with her. At the Proof of Life premiere in Beverly Hills in 2000, she sported a brown leather dress paired with a multi-colored Y2K skinny scarf.

Bold Choice

Ryan's bouncy blonde locs were on unmissable as the actress showed up in an oversized black suit at the premiere of her 1987 film Promised Land. Her textured jacket rose up into a high-neck lace collar, and she brought a matching hat along to accessorize the statement look.

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