Few things have made a comeback in life as great as ’90s trends.
Year after year I think the fashion industry will move on, and they certainly do highlight other ideas and pull from other decades, but for many years now there has still always been a healthy influence of those classic minimalistic looks that the ’90s made so dang famous.
I for sure am a fan of the ’90s aesthetic, but there is one area in particular that I love to pull inspiration from the most: ’90s rom com style.
And Meg Ryan? Easily one of my favorite leading ladies.
Taking Cue From Meg Ryan: Recreating All My Favorite Fall Rom Com Outfits
For my entire life, romantic comedies have been my favorite movie genre. It was often the go-to choice of my parents as I grew up, too, with Meg Ryan specifically being a mainstay on our living room TV.
Even now as an adult, when the cozy seasons roll around, I can’t help but want to curl up on my couch to the sounds of You’ve Got Mail, Sleepless in Seattle, or When Harry Met Sally.
But now, as an adult who is admittedly very obsessed with fashion, I watch my favorite classic rom coms not only for the swooning, feel-good storylines, but for the incredible outfits as well. I’ve even been known to whip out my phone to take notes:
Classic red turtleneck.
Dark blue wash denim.
Tights. All the tights.
After nervously tapping away at my notes app with all the inspiration I was getting, I thought it would be fun to actually recreate these outfits with pieces in fashion today. There are countless outfits among Meg’s movies I would wear in real life, but these 6 outfits, in particular, are my stand-out faves.
Outfit 1- When Harry Met Sally: The On-Trend Color Combo For Fall/Winter
While the movie When Harry Met Sally is technically an ’80s movie (being released in 1989), the fashion had already begun to shift and soften from the bold ’80s looks to the neutral appeal of the ’90s.
Sally is often dressed in outfits I would classify as cozy, minimal, and chic – looks that are both very simple yet entirely admirable. I couldn’t help but swoon over her brown-and-red color combos.
Not only is the color pairing perfectly autumnal, but the colors red and brown are maybe the most shoppable they’ve ever been, being coined as “it” colors of this A/W season.
Outfit 2- You’ve Got Mail: A Cozy Academia Look
This particular look from You’ve Got Mail struck a chord with me when I saw it, simply for the fact that it mixes black, gray, and brown together in a single outfit. Once I noticed it, I realized the entire cast is often seen in these color combos repeatedly. And I was obsessed with it.
I love neutral shades of all kinds mixed together, but these days you typically only see outfits with similar tones. Mixing these three contrasting shades is a fun way to create a bold look without having to wear anything particularly shocking.
There is also something perfectly academic about the tweed-looking skirt paired with black tights, which fits Kathleen Kelly’s bookshop-owner-personality in the best of ways.
Outfit 3- When Harry Met Sally: Inspo For Our Current Ballet Flat Obsession
Pieces like a red sweater and black tights get reused over and over in the movie When Harry Met Sally, which ends up making Sally’s outfits feel very relatable. With a handful of really good wardrobe staples, her outfits actually make for a phenomenal fall and winter capsule wardrobe.
Ballet flats have been on my personal list of items to rewear over and over and over again, and I love that we see a glimpse of the perfect flat on Sally’s feet with sweater tights. Actually, her shoes throughout this entire movie (oxfords, loafers) are all very hot buys yet again this year.
This whole look is classic, yet perfectly on-trend.
Outfit 4- You’ve Got Mail: How To Layer For The Holidays
If there’s one takeaway I’ve gleaned from gathering inspiration off of Meg Ryan’s ’90s romcom outfits, it’s that I need a pair of black tights in my wardrobe, STAT. So many of my favorite looks incorporate a pair.
Kathleen Kelly gives us a lesson in cozy layering with her brown shift dress paired with a classic black turtleneck and, yep, black tights. I took the liberty of updating the shoes to what I’d pair with this look today, but I believe oxfords were paired with the outfit in the movie (as with many of Kathleen Kelly’s outfits). Kathleen Kelly also wears a few great black coats throughout the movie, so I added one here for good measure.
Can anyone say: The Perfect Thanksgiving Dinner Outfit?!
Outfit 5- When Harry Met Sally: Dark Wash Denim and an Ivory Top
Maybe my favorite look of this whole post is Sally’s simple, comfy ivory mockneck and dark wash denim in When Harry Met Sally. It’s the kind of easy look I want to have on rotation weekly.
Lighter washes of blue denim have been phenomenally more trendy in recent years, which is why I think I’m so inspired by all the darker blue washes of the 90s. Lighter denim washes feel more casual, youthful (all great aspects), but this darker look gives off a polished, put-together attitude that instantly elevates the whole look, as simple as it is.
And let’s take note: there are multiple different neutral shades being incorporated together once again.
Outfit 6- Sleepless in Seattle: Loungewear to Live In
Maybe the best part about the fashion in Sleepless in Seattle is that Annie Reed is often cozied up in pajamas and loungewear as she tunes in to listen to the nightly radio talk-show.
While we do get glimpses of some seriously good hooded trench coats and mary jane flats as Annie is at her office or traveling to Seattle, I am most lured in by this undeniably soft-looking loungewear set. At the very end of the scene we get a better glimpse of the top she’s wearing, realizing it may actually be more of an open gray cardigan, but in my world, it’s the perfect cozy crewneck.
Xx,
Amy
Let’s be friends on Instagram! Sharing life from a California beach town, daily style & beauty faves, and never ending Gilmore Girl binge-athons – all with a good dose of adorable toddler content, too.
This is one of my favorite posts you’ve done, thank you! Love Meg Ryan’s style.
This is the best fashion article I have ever read
I love this so much!!!! 😍