Valentine’s Day 2026 is here, and the list of must-watch romantic movies has just got longer. Ryan Murphy’s “Love Story”, a three-part TV series, delves into the romance story of John F. Kennedy, Jr. and Carolyn Bessett Kennedy. With New York as the backdrop, it captures their modern American love story that will surely pull at heartstrings.
Romantic films have long influenced fashion and a select few with New York at their core, comedic or dramatic, continue to add to the city’s allure and influence what we wear. Here is a short list of six cinematic gems and the iconic trends they inspired.
Marilyn Monroe, 1955. Courtesy Everett Collection OMO Norma Kamali, spring 1989. Fairchild Archive
“The Seven Year Itch” (1955)
Marilyn Monroe, standing over a subway grate in a white halter dress, became a fashion legend. The silhouette remains a fashion staple, from dresses to swimsuits.
Ali MacGraw in Central Park, NYC 1969. Michael Kors Fall 2020. Fairchild Archive/WWD
“Love Story” (1970)
Ali MacGraw and Ryan O’Neal star in the “Love Story” title. It’s a gut-wrenching romance fueled with fashion. MacGraw’s look, partly her own, continues to influence fashion. Thanks to Michael Kor,s traces of her signature style remain iconic.
Robert Redford and Barbra Streisand, 1973. Courtesy Everett Collection and Fairchild Archive/WWD
Everett
“The Way We Were” (1973)
Robert Redford and Barbra Streisand’s fashion moments span three decades (1930s-1950s) in “The Way We Were.” WWD noted its lavish backgrounds as “full-color fashion layouts,” gorgeously framed in the political metaphors of love and tragedy. Streisand’s red carpet moment and costumes continue to inspire the runway.
Cher and Nicolas Cage, 1987. Courtesy Everett Collection Cher at Balmain, 2023. WWD
“Moonstruck” (1987)
Cher’s memorable transformation from a dowdy Italian widow residing in Brooklyn, NY, stole the movie. Her black strapless dress, ruby red shoes and lips, and voluminous jet black mane were a Cinderella moment. The look continues to inspire, with Cher walking the 2023 Balmain runway show, her hair a direct nod to her Moonstruck-era style.
Eddie Murphy and Robin Givens, 1992. Courtesy Everett Collection Joseph Abboud, fall 1992. WWD
“Boomerang” (1992)
This rom-com weaves 1990s office culture into its fashion narrative. Eddie Murphy’s tailored suits and Robin Givens power suits were of the moment, but celebrate a lasting genre of fashion, then and now.
“Sex and the City” the series (1998-2004)
Sarah Jessica Parker, 2011. Sex and the City cast, 2000. Fairchild Archive/WWD
An undeniable icon of NYC and fashion, the HBO series, featuring Sarah Jessica Parker and co. elevating designer wear to new heights from the start. Every outfit, including those Manolo Blahnik pumps, became a cultural moment.
New York and fashion remain at the heart of some of the most memorable love stories, bridging the fantastical and the real across decades.
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