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!
Today being my wedding day (congratulations to me!) feels like an appropriate time to revisit the style of one of my favorite romantic comedies, When Harry Met Sally. In addition to being a famously great fall movie, Rob Reiner’s chronicle of enemies-becoming-friends-becoming-lovers also demonstrates a surprising parade of great autumnal menswear, from Billy Crystal’s cozy sweaters to military surplus jackets.
For those unfamiliar with the story, we begin in the spring of 1977, when Harry met Sally (Meg Ryan) on a road trip from the University of Chicago to New York City. Both are recent UChi grads who get along like oil and water as he shares his contention that men and women can never be just friends, a point he drives home with a comment that Sally interprets as a misguided pass at her, given that she only knows him because he’s dating her friend.
The two part ways upon reaching New York, only to find themselves on the same flight five years later, both now in serious relationships. A somewhat matured Harry shows a willingness to be friends, but Sally recalls his previous tenet disavowing friendships between men and women and the two once again separate after a short trip.
Yet another five years pass before Harry spies Sally from the personal growth section of Shakespeare & Co. bookshop in the Upper West Side. She’s newly single and he’s recently divorced, sharing their respective miseries and neuroses over coffee.
Sally: At least I got the apartment.
Harry: That’s what everyone says. But, really, what’s so hard about finding an apartment? What you do is look in the obituary section. You see who died, find out where they lived, and tip the doorman. What they could do to make it easier is combine the two. You know, Mr. Kline died yesterday, leaving behind a wife, two children, and a spacious three bedroom apartment with a wood burning fireplace.
Finally, Harry seems willing to move past his half-baked hypothesis of a decade earlier as he and Sally evolve their acquaintanceship into a deep and sincere friendship.
Harry: You know, you may be the first attractive woman I’ve not wanted to sleep with in my entire life.
Sally: That’s wonderful, Harry.
What’d He Wear?
Harry wears what may qualify as “smart casual” while trolling the self-help shelves at Shakespeare & Co., clad in a tweed sports coat layered over a denim-like shirt with jeans and loafers. (To Harry’s credit, the outfit came in second place when Sophia Benoit published in GQ a ranking of all 32 of Billy Crystal’s tracked costume changes.)
Tweed may only come second to corduroy on my short-list of favorite jacket cloths to wear with jeans, as famously exemplified by Robert Redford’s wintry layers in Three Days of the Condor. Harry wears a professorial taupe tic-woven tweed, comprised of lighter multi-colored yarns woven in staggered sequence against the dark taupe woolen tweed ground.
Harry’s single-breasted sports coat is cut in a generally classic style, with straight shoulders and front darts that add shape. The notch lapels roll to two brown woven leather buttons, positioned at a fashionably lower stance, and the jacket is styled with the usual welted breast pocket, straight flapped hip pockets, and single vent. The sleeves are gently roped at the shoulders, with professorial brown suede patches over the elbows and three decorative woven leather buttons on each cuff.
Harry wears a casual shirt made from a rich indigo denim-like cotton, a popular shirting through the late ’80s into the ’90s, though Harry avoids Jay Leno or Jerry Seinfeld cosplay by wearing a darker wash shirt with a trimmer fit… and no tie!
The shirt has a point collar, worn open, with smoke-colored plastic buttons up the front placket. The two chest pockets are each covered with a rounded flap, although the jacket mostly covers them to the extent that we can’t tell if they close with a button or not.
Harry’s favorite jeans are his medium-wash Levi’s, well-chosen here as the blue denim is a shade lighter than his shirt while also providing textural harmony with the coarse finish of his sports coat. He wears a brown leather belt with a shining gold-finished single-prong buckle, the belt leather coordinating neatly with his brown leather moc-toe penny loafers. As the tailored jacket makes this one of Harry’s dressier casual outfits, despite the jeans, his loafers are a smarter complement than his usual Nike sneakers.
Oh, but those white sneakers I was talking about? Harry does briefly wear them with this jacket and jeans during a later vignette depicting his and Sally’s growing friendship. For this instance, he now wears a brown shirt with a button-down collar that restrains it to within the V-neck of his tan Fair Isle-knit sweater vest.
How to Get the Look
While Harry’s reunion with Sally isn’t exactly a romantic encounter, his smart tweed sports coat, casual shirt, loafers, and jeans provides a sophisticated yet versatile template when dressing for a fall date.
- Taupe tic-woven tweed single-breasted 2-button sport jacket with notch lapels, welted breast pocket, straight flapped hip pockets, brown suede elbow patches, 3-button cuffs, and single vent
- Indigo denim cotton shirt with point collar, front placket, two flapped chest pockets, and button cuffs
- Blue denim Levi’s jeans
- Brown leather belt with gold-finished single-prong buckle
- Brown leather moc-toe penny loafers
Do Yourself a Favor and…
Check out the movie.
What’s the statute of limitations on apologies?