Home Fashion Fashionista’s Pop Culture Style Icons: Steph Always Envied Annie From ‘Sleepless in...

Fashionista’s Pop Culture Style Icons: Steph Always Envied Annie From ‘Sleepless in Seattle”s Hair


This week at Fashionista, we’re celebrating all things at the intersection of fashion and pop culture — including the nostalgic sartorial moments that were formative to our style growth. In our series, Fashionista’s Pop Culture Style Icons, we obsess over the characters who have influenced our wardrobes the most, even to this day.

Photo: Gifs.com

Photo: Gifs.com

For most of my childhood, my family owned only two movies on video, both of which featured Tom Hanks: “Big” (classic) and “Sleepless in Seattle” (rom-com, also classic). So naturally, I watched those over and over again in between episodes of “Rugrats” and “All That.” Let’s just say I came to know them both quite well. 

Now, Nora Ephron wrote and directed some quality films in her day (controversial take, I know!) but I’m gonna just put it out there that “Sleepless” is the best. Sure, “When Harry Met Sally” comes quite close, but I’d pick Hanks over Crystal any day. While “You’ve Got Mail” is a nostalgic ’90s Upper West Side love letter wrapped in a cozy new sweater your mom bought you for back-to-school season, it’s also A TOTALLY TRANSPARENT KNOCKOFF OF “SLEEPLESS” CREATED SOLELY TO PLACATE FANS BEGGING FOR MORE RYAN-HANKS SCREEN TIME! Wake up, sheeple! 

You're Annie? Photo: Giphy

You’re Annie? Photo: Giphy

Ignoring the creepiness of the premise — an 8-year-old boy having a strange fixation on getting his dad laid — “Sleepless in Seattle” has a lot going for it. For one, it’s sprinkled with the best cameos ever. Every role, however small, is filled with a somebody (though, in some cases, that’s because it was before they were somebodies): Rita Wilson, Victor Garber, Gaby Hoffman, Bill Pullman, David Hyde Pierce, Rosie O’Donnell, Rob Reiner… what a delightful ’90s crew. But as a small child watching a rom-com not particularly geared toward small children, it was, in part, the fashions and — the budding beauty editor that I apparently was — the hair, that kept me so enthralled with the film.

And all I could say was... Photo: Giphy

And all I could say was… Photo: Giphy

Say what you will about early ’90s fashion, but Meg Ryan, drop-shoulder jackets and flowy, soft hairstyles were MFEO (that’s made for each other, as you know if you’re also a fan of the film). As Annie Reed, a journalist based in Baltimore, Ryan wore a wide range of Career Lady™ looks that showed she was goal-oriented and had her shit together, as any ’90s movie heroine must. There were blazers, pantsuits and trench coats aplenty, but none of them were ever overly stiff or tailored. They seemed to communicate that she was smart and professional, yes, but not in a stuffy way. She was fun. She’d be a cool mom. She wasn’t like Victoria, Sam’s girlfriend that Jonah reminded me how to feel about:

You said it, Jonah. Photo: Tumblr

You said it, Jonah. Photo: Tumblr

And her hair — wispy, ropy and oh-so-shiny — was mesmerizing to me. Unlike Ryan’s fluffy ’80s Sally Alright coif or early-aughts Kate (of “Kate and Leopold”) choppy, straightened-to-oblivion bob, her hair for this film manages to be both nostalgic and timeless, even looking back at it now. The long braids, soft layers and honey-blonde highlights she favored were all hallmarks of early ’90s hair trends, but they’re just so damn pretty that I still want them, even today.

Epic '90s hair situation. Photo: Giphy

Epic ’90s hair situation. Photo: Giphy

As a tribute to Annie, I’ve pulled together a selection of pieces I could totally see the 2017 version of her wearing while late-night Tweeting at Dr. Marcia Fieldstone, clinical psychologist and the friend you never had. There are also a few hair products in the mix that I’ve found to be helpful for getting me a step closer to that ropy, super-shiny Annie Reed hair I’ve coveted for the past two decades.

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