Billy Crystal and Meg Ryan in When Harry Met Sally (1989)
Vitals
Billy Crystal as Harry Burns, sarcastic political consultant and recent divorcée
New York City, Fall 1987
Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham
WARNING! Spoilers ahead!
Background
One of the most aesthetically pleasing fall movies, Rob Reiner’s romantic comedy When Harry Met Sally celebrated its 35th anniversary earlier this year. Billy Crystal and Meg Ryan—who celebrates her 63rd birthday today—star as the titular enemies-turned-friends-turned lovers.
What’d He Wear?
Harry Burns’ wardrobe blends typical ’80s tailoring, civilian twists on military staples, and cozy sweaters that have invited both analysis and admiration, including Sophia Benoit ranking all of Harry’s 32 costume changes for a GQ feature published ahead of the film’s 30th anniversary in 2019.
For the famous sequence following the two friends walking through Central Park during its autumnal peak and doing funny voices at the museum (“I would be proud to partake of your pecan pie”), Harry wears a civilian variation of the brown leather AN-J-3 flight jacket. The U.S. military authorized the AN-J-3 in 1943 to standardize its flight jackets across branches, combining elements of the Army’s iconic A-2 and the Navy’s mouton fur-collared M-422A.
Essentially an M-422A with the A-2’s plain cllar, the AN-J-3 features a straight zip front, two flapped hip pockets, ribbed-knit cuffs and hem, a storm flap, button-down pocket flaps, and bi-swing pleats. Though it was only issued through World War II, the AN-J-3’s iconic design lived on through the decades as civilian outfitters paid tribute to it with contemporary recreations like Harry wears.
Now firmly friends, Harry and Sally are coordinated in their busy dark-gray sweaters with red knitted patterns.
Benoit ranked the outfit at #13, praising the jacket’s cool factor as “if Karamo Brown and Paul Newman had a fashion baby” but criticizes what she calls “that horrendous sweater”:
It looks like something a guy in a band that’s almost famous dug out of a bin at Goodwill and now wears ironically. The sweater looks like what a printer spits out to test ink levels. It almost undoes any of Harry’s raw sexual power that he brings to the film. If only God would deliver us from that sweater.
The sweater in question does defy a simple description, patterned with horizontal stripes in alternating widths—red across the chest and light-gray below it, always alternating with dark-gray stripes. While each stripe is marled between its main color and black threads, the stripes are also overlaid with knitting that presents jagged black lines staggering down the body of the sweater. The high neckline is a scalloped V-neck, trimmed in black and both shades of gray with a single button left undone. Harry layers the sweater over a black polo shirt, though little can be seen except two mixed beige 4-hole buttons at the top.
Rather than his typical Levi’s jeans and Nike sneakers, Harry wears surprisingly formal slacks and oxfords—all black. The reverse-pleated trousers have side pockets and plain-hemmed bottoms, which break over the tops of his black leather cap-toe oxford shoes. He avoids disruption between the trouser and shoe by wearing plain black socks.
Though Harry only wears the AN-J-3-style flight jacket on screen with the aforementioned outfit, it does appear to be slung over the back of his chair during the famous “I’ll have what she’s having” scene at Katz’s Delicatessen on East Houston Street.
While Harry now wears his usual mid-blue denim jeans, he wears yet another chunky gray patterned sweater—this one a hefty crew-neck pullover with a busy white, yellow, and taupe overcheck against the charcoal-and-gray horizontal-striped ground. (For what it’s worth, Benoit ranked this ensemble two positions lower, likening Harry’s appearance to “a ’90s divorced dad who takes his kids to Bob Evans on the weekends because all he has in the fridge is Coors Banquet and Hungry-Man frozen dinners.”)
Harry layers this sweater over an indigo denim button-up shirt, possibly the same shirt that he earlier wore with a tweed sports coat and jeans when he and Sally first rekindled their acquaintanceship at Shakespeare & Co. bookstore.
How to Get the Look
Billy Crystal in When Harry Met Sally (1989)
Harry dresses down a cozy sweater and black slacks and oxfords with a worn-in flight jacket that pays tribute to a decades-old military pedigree, finding a comfortable balance between form and function during a casual fall day out with a friend.
- Brown leather AN-J-3-inspired flight jacket with shirt-style collar, straight-zip front with storm flap, bi-swing back pleats, patch pockets with single-button rectangular flaps, and ribbed-knit cuffs and hem
- Black polo shirt
- Black, red, and two-toned gray marled knit long-sleeved sweater with single-button scalloped V-neck
- Black reverse-pleated trousers with side pockets and plain-hemmed bottoms
- Black leather cap-toe oxford shoes
- Black socks
Do Yourself a Favor and…
Check out the movie.
The Quote
I had my dream again where I’m making love, and the Olympic judges are watching. I’d nailed the compulsories, so this is it—the finals. I got a 9.8 from the Canadian, a perfect 10 from the American, and my mother—disguised as an East German judge—gave me a 5.6. Must have been the dismount.
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