When Harry met Sally, not only did their banter-filled friendship begin, but so did a series of iconic fashion moments. The tweed blazers, fisherman knits, and bowler hats commanded (almost) as much attention as Sally did at the deli. It’s 32 years later, and we’re still as obsessed as ever.
In fact, this feels like the most relevant time to dress like we’re in the late ‘80s. High-waisted jeans with a croc belt and loafers? So 2021 of you, Meg Ryan. And it’s not just our rom-com queen whose outfits stole our hearts—some of Harry’s cozy looks landed on our list as well.
Here’s to singing “The Surrey With the Fringe on Top” and acquiring more cable knit sweaters than our closets can handle. Oh, and rewatching this movie for the 200th time.
1. The Central Park stroll look
Source: Metro-Goldwyn-Mayer Studios Inc.
sweater | sweater (plus-size) | blazer | blazer (plus-size) | trousers | trousers (plus-size) | gloves | booties
It’s the season for wearing multiple layers, strolling through Central Park, and ordering Apple Pie a la Mode (heated, with the ice cream on the side)—AKA When Harry Met Sally season. Celebrate the occasion in the instantly recognizable outfit that Sally dons on the movie poster: a pair of pleated trousers, printed pullover, gray blazer, and bowler hat. This color palette features nearly every neutral color in existence, making it the perfect fall-weather uniform.
2. The mom jeans and turtleneck look
Source: Metro-Goldwyn-Mayer Studios Inc.
turtleneck | turtleneck (plus-size) | jeans | jeans (plus-size) | tote | belt | loafers | socks
Mom jeans and a white turtleneck might sound a little boring, but surprise! Meg Ryan turns a simple outfit into something simply adorable. The trick? Tucking in the shirt and incorporating a belt to accentuate the high-waisted look. Loafers and white socks are just the extra bit of charm any main character needs. There’s a reason #megryanfall is trending on TikTok.
3. The loungewear look we want to live in
Source: Metro-Goldwyn-Mayer Studios Inc.
fisherman’s sweater | sweatpants | sweatpants (plus-size) | slippers
If this isn’t a whole mood, we don’t know what is. Harry Burns achieved peak coziness in this scene, and thankfully, we can all emulate it. Just cancel all plans, grab your favorite Stephen King novel, and pair some sweats with a fisherman’s sweater. A monochrome fit that’s as effortless as it looks? That is just like you, Harry. And if you must leave the house, you can always swap your sweats with black leggings and boots.
4. The diner look
Source: Metro-Goldwyn-Mayer Studios Inc.
cardigan | cardigan (plus-size) | button up | button up (plus-size) | belt | shorts | shorts (plus-size) | knee-high socks | chunky loafers
Who knew that a cardigan, bermuda shorts, and knee-high socks would be the perfect attire for transitional weather (or a cross-country road trip with your inevitable soulmate)? Sally did, of course, just like she knew exactly how to order a chef salad.
5. The denim-on-denim look
Source: Metro-Goldwyn-Mayer Studios Inc.
denim shirt | denim shirt (plus-size) | blazer | blazer (plus-size) | belt | jeans | jeans (plus-size) | loafers
Before we address Sally’s impeccable-ness, let’s stop and appreciate Harry’s double denim moment. This is one of those menswear-inspired outfits you can put together with the basics you already own. Denim on denim isn’t always the easiest to pull off, but with a wool blazer, it’s instantly timeless.
6. The corduroy blazer look
Source: Metro-Goldwyn-Mayer Studios Inc.
blazer | cable-knit sweater | sweater (plus-size) | tote | watch | jeans | jeans (plus-size) | booties
Too much pepper in your paprikash may be one thing, but too many blazers in your wardrobe is impossible. Sally sports several throughout the film, and while it’s difficult to choose a favorite, this chocolate corduroy blazer may beat out all the rest. Layered over a red cable knit sweater, it becomes the fall outfit. We’ve said it before and we’ll say it again: We’ll wear what she’s wearing.
