25 Years Later, You’ve Got Mail Has Style That Still Holds Up

It is not a unique thing to love You’ve Got Mail. And as the movie arrives at its 25th anniversary this December, I can say with a fair amount of certainty there will be no shortage of fawning Instagram captions about bouquets of freshly sharpened pencils and think pieces on the ever-compelling chemistry of Meg Ryan and Tom Hanks. Yet while I logically know the film has legions of devotees claiming it for themselves, I have always held my own small piece of fandom close to my heart — my own connection to the work, after all, is specifically special to me. I still remember standing in my best friend’s kitchen the night after we saw it in the theaters, completely taken with the unstudied affluence and cerebral banter of the sophisticated New York City characters I has just absorbed for nearly two hours. Oh, to spontaneously find myself frolicking through a Halloween street fair on a bright fall afternoon! Or to casually drop over $100 on hardcover books without even giving it a second thought. I longed to stand in windy lines at gourmet food stores; I dreamed of waiting for my potential soulmate in a crowded coffee shop.

But, perhaps more than anything else, I pined for the clothes I saw on screen — or, better put, how they were put together. There was nothing flashy or overtly designer about the way these late ‘90s yuppie urbanites dressed; their closets were filled with the sort of pieces that seemed, to the untrained eye, easy enough to source. There were shackets haphazardly thrown over button-downs (shout out to Joe Fox), plain belted khaki pants and a simple white tee (a Kathleen Kelly special), giant chunky knits paired with a prim little white blouses (Christina Plutzker made it look so cozy and cute). And Parker Posey’s part as Patricia Eden, while a rather small one, was made utterly memorable by her ‘90s power b*tch uniform of meticulous layers of black, accessorized with discreet hair barrettes. There was something in the exacting fit and perfect slouch of every actor’s look that felt quietly luxurious decades before it was even a thing. Because to just randomly toss on your basics and look like you stepped out of a rom-com? Now, that’s a flex.

When You’ve Got Mail first hit theaters in 1998, I was 11 years old and in 6th grade. In my small upstate New York town, the popular kids dressed in head-to-toe Gap bootcut jeans and American Eagle polo shirts. If you were especially lucky, maybe your mom drove you to the big mall an hour away to buy the same look at Abercrombie & Fitch for a higher price. Gazing at a pixie-ish Meg Ryan flit her way around the screen in her effortlessly layered top, knee-length skirts, and opaque black tights (oft coupled with a nondescript pair of loafers... in hindsight, they were Prada perhaps?) completely blew the lid off how I thought about clothes. There was just something so compelling about her pristinely tucked-in high-neck shell tops, paired so nonchalantly with an open, hip-skimming cardigan. This, to me, was more glamorous than any va-va-voom gown on the red carpet or extra high heels. To simply embody one’s garments so fully that they became an extension of your being seemed like a feat of near-magic.

Nothing in my wardrobe ever seemed to slip on and seamlessly settle on my body in the second-skin way Ryan’s did. On the verge of awkward adolescence (and with a limited budget), most everything I bought felt like it was too tight in some places, too loose in others. Even to this day, I still often think Ryan meeting Hanks in the final scene of the movie. Her steel grey dress and translucent elbow-length cardigan seem deceptively simple, but on second glance, every detail is so deeply considered: the matching cloudy hues, the sweet fit-and-flare skirt (which, may I add, is on the longer side, but not so much so that it looks dowdy with Ryan’s flats), the intriguing mix of open-weave and nubby linen textures. Orchestrating that kind of subtle sartorial genius is so much harder than leaning on one bold piece to carry the rest of one’s outfit.

Of course, I, living in my pre-teenage suburban bubble, had no idea that the costumes were quite reflective of a much greater moment in fashion. Hot off the heels of a grunge-fueled era of oversized flannels and ditzy floral dresses, the industry had moved into an era of sleek and streamlined understatements. OG minimalists Calvin Klein and Helmut Lang were highly influential; meanwhile, Marc Jacobs had just zeroed in on stark neutrals and unfussy silhouettes for his buzzy debut at as creative director of Louis Vuitton. Although there were already harbingers of the bubblegum brightness of Y2K styles on the horizon (ahem, most everything the Spice Girls ever wore), these last few years of the ‘90s runway collections were crisp and cool palette cleansers.

The idea of starting fresh definitely appealed to me at the time. I was particularly unmoored that first year of middle school, like I didn’t quite fit into my younger identity, but was still totally uncomfortable when conversations turned toward topics like crushes, bras, and the proper application of eyeliner. It felt like all my friends had suddenly gotten a memo on stepping beyond the snuggly world of childhood I had been living in for the last decade, and I was left to figure a path out for myself. In You’ve Got Mail, I didn’t exactly find one — but I did see where I wanted the journey to eventually lead me. And I wanted to dress the part: I began swiping my mom’s J.Crew catalog, in which I’d study the combinations and circle the pieces I wanted with a fat ball point pen. Soon, I became probably the only kid in 7th grade who wore wide leg charcoal wool pants and deep wine-colored Angora sweaters (both purchased on super sale with assistance from my allowance) on the regular, but in this one small instance I didn’t mind sticking out from my peers.

Years later, I did eventually move to NYC for college, and I’ve never left. Living here for 18 years, I’ve had my fair share of shopping for overpriced groceries and hustling home to get ready for a party, plenty of cute and witty conversation. And all the while, I’ve tried on plenty of different style identities, from a Gossip Girl-inspired girly dress and headband fixation to an indie sleaze rocker moment. But whenever everything in my wardrobe begins to seem all wrong, and I need a blank slate to work from, it’s comforting to know that — much like watching You’ve Got Mail for about the ten thousandth time — a simple pair of loose trousers and a classic sweater will never, ever let me down.