Meg Ryan's Best Outfits In When Harry Met Sally, Ranked By Timelessness

There are plenty of pictures of Meg Ryan that showcase her peak '90s style, but her outfits in the '80s rom-com "When Harry Met Sally" are among her best. In fact, Ryan's wardrobe was so stylish in the film that the actor became known as a fashion icon, and her timeless style continued to provide outfit inspiration for the decades to come.

While playing the character Sally Albright, Ryan embraced some classic pieces, but her outfits were also elevated with distinctive accessories. In a 2023 interview with Glamour, Ryan shared details about her favorite looks from the film. "This was just the costume designer's idea of, like, New York in the '80s," Ryan said. "I think my favorite is whatever the librarian look is, with the bowtie. It's fantastic," she added, noting that the character's bouncy blowout in the opening scenes mirrored that of her own hairstyle in high school.

Although most of Ryan's on-screen outfits featured timeless basics, her unique accents made some looks more enduring than others. From earthy hues, knitted sweaters, and tailored trousers to bowler hats, neckerchiefs, and tweed, Ryan's "When Harry Met Sally" wardrobe seamlessly blended modern trends with a vintage flair. Her more timeless looks featured retro pieces that have returned to mainstream fashion trends throughout the decades, making them enduring staples of her style. In contrast, her less classic looks were built on basic pieces but were elevated using bold silhouettes and accessories that added a more eclectic and daring edge.

Meg Ryan's tailored look as Sally Albright while strolling around New York City is among the most iconic rom-com outfits to recreate for a main-character moment. However, while her ensemble was built on basics, her black leather gloves and wide-brimmed brown bowler hat added a daring edge to her look that lessened the timelessness of her look. Still, despite her unique accents, including a black sweater featuring red and white dots, Ryan also wore muted brown trousers and a gray blazer that emphasized the character's sophisticated allure — particularly when paired with her cross-body bag.

Meg Ryan's outfit in her final scene as Sally Albright captured her character's chaotic yet chic allure. While the simplicity of her monochrome was relatively timeless, her white blouse looks like it was made for the '80s era. The actor wore a glossy white blouse that featured bold '80s-style shoulder pads and a criss-cross neckline. In recent years, power dressing has become outdated, and white blouses have been reimagined with significantly smaller shoulder pads. Ryan's criss-cross neckline has also become relatively obsolete in fashion, especially as deep V-neck trends take over. This look, although gorgeous, is far from timeless.

When Sally Albright attended Marie's wedding, Meg Ryan was dressed in a timeless vintage-style velour gown. Her emerald green gown featured a corset-like bodice that extended into puff sleeves and a ballgown-inspired hemline. While different shades of green, including the emerald hue of her gown, have remained an autumn staple for years, the milkmaid silhouette of her dress nodded to more retro glamour trends. While her look was timeless, contemporary versions of Ryan's velour gown feature body-conscious silhouettes.

In one of the first scenes in "When Harry Met Sally," Sally Albright and Harry Burns sought refuge at a diner during their tense road trip. Meg Ryan was dressed in another rather timeless look that would have been even more enduring without her bold knee-high socks. She wore a muted butter-yellow shirt, minimal high-waisted beige shorts, and a navy cardigan — basic pieces that have remained timeless. While her look was completed with a simple black belt, her knee-high black socks were particularly distinctive and emphasized the character's bookishness.

When Sally Albright ran into Harry Burns for the second time, she was wearing a vintage-inspired ensemble that was timeless to an extent. While Meg Ryan's tweed blazer was certainly an enduring staple, her vibrant neckerchief was not. Tweed jackets have been reimagined in recent years, but classic styles like Ryan's have maintained their lasting appeal throughout. Regarding neckerchiefs, they returned as a dominant fashion trend in the 2020s, but before that, the accessory fell out of favor in fashion. Therefore, while Ryan's tweed blazer certainly gave her look a timeless appeal, her neckerchief added an eclectic edge at the time.

Meg Ryan left a lasting impression after her iconic deli scene, and her memorable performance certainly made up for her muted ensemble. The actor wore a casual black cable-knit sweater with a deep V-neckline. Her deep neckline made room for her white '80s-style blouse that featured black embroidery below the collar. The base of her look was incredibly timeless, purely due to its simple components. However, since the popularity of brooches has fluctuated in fashion over the years, the timelessness of Ryan's ensemble was compromised by the embroidered brooch-style detailing on her shirt. 

When Sally Albright bought her Christmas tree, Meg Ryan was wearing a longline tweed jacket and tailored trousers. As a fall fashion icon, Ryan's repeating use of tweed throughout the film likely helped popularize the fabric as a fall staple. Tweed jackets have become known for their versatility, which confirms that this look was one of Ryan's most timeless. Her accessories included a cross-body bag — a staple in her character's wardrobe — and a fashionable long scarf. 

Sally Albright's argument with Harry Burns outside her apartment may have marked a turning point in "When Harry Met Sally," and it made for one of Meg Ryan's most enduring fashion moments, too. Her look featured a classic pair of mom jeans paired with a white turtleneck and a simple brown belt. While high-waisted styles veer in and out of fashion, dark denim and relaxed silhouettes have proven their timelessness. Tucked into her jeans, Ryan's versatile white turtleneck added a sophisticated element to her ensemble.

Sally Albright reached for her classic mom jeans again as she navigated the aftermath of her fallout with Harry Burns. Featuring timeless jeans and a classic turtleneck, this look was arguably one of Meg Ryan's most enduring outfits in "When Harry Met Sally." While Ryan's most timeless ensembles are often the simplest, the cropped balloon sleeves of her plum turtleneck added an eclectic edge without sacrificing all timelessness. While wearing purple was particularly popular in the '80s, the color has also proven that it has some lasting power by dominating fall fashion over the years.

Meg Ryan's red sweater and brown blazer were part of her most timeless look. The outfit also made for one of the most nostalgic style moments from hit '80s movies that give us all the fall feels. With a long history in fashion, turtlenecks have certainly proved their timelessness. Not only did they dominate fashion in the '70s, but they returned as a wardrobe staple in the '90s, too. What's more, in the 2020s, the turtleneck fad also retained its prominence in fashion. Once again, Ryan wore classic straight-leg jeans and her signature bag — a practical addition to any layered fall look.

Meg Ryan wore several timeless ensembles in "When Harry Met Sally." We examined each outfit to identify the style elements that have maintained their wardrobe staple status. We also considered whether those elements had kept their original form over the decades, or if they had been reimagined. Looking at these style elements with a long history, it became clear which parts of Ryan's outfits are truly ageless, and which parts are not. The outfits with the most noticeably enduring elements, particularly those that were continuously produced in their original form, were ranked first. However, outfits featuring elements that had largely fallen out of favor were ranked last.