Rom-Com Queen Meg Ryan's Best & Worst Looks From Her Iconic Movies

While Meg Ryan has been a successful Hollywood star since the late '80s, the actor remains best known for her '90s rom-com roles — and the many looks she wears in these movies. Ryan, who is among the famous '90s actors who are practically unrecognizable now, has starred in a variety of genres, but her fans adore seeing the star in wholesome and funny love stories.

In the rom-coms she has given us so far, Ryan has played a plethora of different women, all of whom have had their own style. Fashion-wise, the actor is best known for her nostalgic '90s wardrobe, and many of the characters she played perfectly showcase it. Some, on the other hand, have worn questionable combinations. While these may have served a purpose in terms of the story, they are bad fashion moments nonetheless. From a classic and timeless combo in "Sleepless in Seattle" to a busy and poorly tailored wedding dress in "Prelude to a Kiss," these are the best and worst fashion moments that rom-com queen Meg Ryan has given us on-screen so far.

The 1989 rom-com "When Harry Met Sally" may be decades old, but the beautiful love story remains a fan favorite of the genre. In the film, Meg Ryan portrays journalist Sally Albright, whose style is the epitome of late'80s and early '90s fashion. In fact, the red sweater, jeans, and brown blazer combo the character wears during a cold-weather walk is also among the nostalgic style moments from hit '80s movies that will give you all the fall feels.

Meg Ryan's pure talent throughout her career is perhaps best summed up by the fact that she portrayed three different characters in the 1990 rom-com "Joe Versus the Volcano." In the film, Ryan plays DeDe, Angelica Graynamore, and Patricia Graynamore, and while not all three have awful style, DeDe's wardrobe could have certainly benefited from a few more stylish pieces. Of course, her fashion choices reflect her personality, but the frumpy polka-dot dress she wore in one scene is definitely among Ryan's not-so-fashionable on-screen moments.

The 1993 rom-com "Sleepless in Seattle" is yet another Meg Ryan classic that remained popular decades later. In the film, Ryan plays newspaper reporter Annie Reed, and her style, similar to Sally Albright's, is all about simple and timeless pieces that work beautifully together. The white sweater and mom jeans combo? A look that works regardless of trends, especially when combined with white socks and brown accessories.

Red and leopard print are a combination that usually works well together, but in "Addicted to Love," Meg Ryan's character shows us just how it can also go wrong. In the 1997 rom-com, Ryan portrays photographer and motorcyclist Maggie, who pairs a leopard-print top with a shiny red velvet blazer. While the two pieces ended up clashing for attention, it is primarily the finish of the jacket that aged poorly.

Plenty of Meg Ryan characters have rocked simple and preppy looks through the years, which makes it hard to believe that the actor didn't have some kind of input in the on-screen looks. In the 1995 rom-com "French Kiss," Ryan plays history teacher Kate, who knows that wide-legged pants pair particularly well with a chic striped shirt. A simple belt and tank top underneath allowed the character to look stylish, even with the shirt wrapped around her waist.

The 2023 rom-com "What Happens Later" is a particularly important film for the Hollywood star, as Meg Ryan not only starred in it, but also directed it. In the project, Ryan plays Willa, whose airport fashion needs a bit of improvement. The character wore a wide, prairie-like dress and a floor-length black coat over it — a combination that looked completely mismatched. Then again, due to luggage restrictions, airport fashion is its own category, so perhaps we shouldn't judge.

There have been plenty of occasions where Meg Ryan showcased her peak '90s style, and her characters from that era certainly followed suit. In 1998, Ryan starred in the romantic comedy-drama "You've Got Mail," in which she played bookstore owner Kathleen Kelly. Needless to say, most of Kelly's looks were fabulous, but one we're particularly fond of is the black turtleneck dress, which showcases a chic and preppy take on your classic LBD. There are many ways to style a little black dress, and Ryan's version in this movie lives in our minds rent-free.

While technically not a rom-com, the 1992 romantic fantasy film "Prelude to a Kiss" still garnered a spot on our list, mainly thanks to the poorly tailored and slightly mismatched wedding gown that had its moment in it. Meg Ryan plays bartender Rita Boyle in the project, and while the wedding dress that she wears could have been in the best category with minor changes, it ended up on the other side nevertheless. Various angles show the poor tailoring around the bust, and the lace, off-the-shoulder straps, and gloves simply add too much to the look.

The rom-com "Kate & Leopold" shows how wearable a brown leather jacket is, as Meg Ryan's character in it styles it to perfection. In the 2001 film, the Hollywood star portrays Kate McKay, who clearly knows that brown leather jackets are just as fabulous as black ones. McKay pairs hers with a brown shirt layered over a white one, which peeks out only around the collar. Classic straight-cut jeans, brown shoes, and a belt finish off the casual fall-time look.

In the 2000 comedy-drama "Hanging Up," Meg Ryan plays Eve Mozell Marks, whose fashion choices have been both fabulous and questionable. In particular, it's when the character pairs a gray maxi skirt and a white long-sleeved shirt with white socks and a white belt that most of us were confused. A pair of jeans would have fixed the fashion faux pas, as the gray skirt, thanks to its material, made the outfit kind of look like pajamas.