Vitals

Billy Crystal as Harry Burns, sarcastic political consultant and recent divorcée

New York City, Fall 1988

Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham

WARNING! Spoilers ahead!

Background

Rob Reiner’s 1989 romantic comedy When Harry Met Sally is often (deservedly) included on lists compiling the greatest fall movies. As tomorrow will be the first day of autumn here, I return to my own frequent celebration of Billy Crystal’s fall wardrobe as Harry—specifically during his fateful visit to comfort Sally (Meg Ryan) at her apartment after she learns that her ex-boyfriend is getting married.

Sally: Why didn’t he want to marry me? What’s the matter with me?
Harry: Nothing.
Sally: I’m difficult.
Harry: You’re challenging.
Sally: I’m too structured, I’m completely closed off.
Harry: But in a good way.
Sally: No, no, no, I drove him away. And, I’m gonna be forty.
Harry (doing the math): When..?
Sally: Someday.
Harry: In eight years.
Sally: But it’s there. It’s just sitting there, like some big dead end. And it’s not the same for men. Charlie Chaplin had babies when he was 73.
Harry: Yeah, but he was too old to pick them up.

Harry and Sally had been there for each other for two years, but tonight the two best friends finally consummate the unspoken attraction during their two years of intense companionship. Sally wakes up content and forward-looking, but the disoriented Harry swiftly re-layers to depart, evidently hoping to salvage their previously platonic dynamic. Before they continue to leave too much uncommunicated in the vulnerable days that follow, Harry and Sally each separately call their respective best friends Jess (Bruno Kirby) and Marie (Carrie Fisher) to debrief… of course, Jess and Marie are married to each other so they take the calls from their shared bed.

After talking Harry and Sally though their romantic confusion, Marie asks Jess for affirmation in what remains one of my favorite exchanges from Nora Ephon’s incredibly quotable screenplay:

Marie: Tell me I’ll never have to be out there again.
Jess: You will never have to be out there again.

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What’d He Wear?

Part of my fondness for Harry Burns’ wardrobe comes from our shared reliance on mil-spec or military-inspired outerwear, from his civilian interpretation of a World War II-era leather AN-J-3 flight jacket to his surplus nylon CWU flight jacket during the New Year’s Eve-set finale. One repeating item from Harry’s wardrobe, most prominently worn during the significant scene where he and Sally finally consummate their attraction, is another martial staple: a drab green four-pocket field jacket.

Like his leather flight jacket, Harry’s field jacket is a purely civilian product though it clearly takes style queues from the iconic M-65 that the U.S. Army first authorized during the Vietnam War. The shell is a sage-green cotton, which appears smoother and lighter-weight than a true M-65’s olive cotton sateen fabric. Despite a somewhat simplified overall appearance, Harry’s jacket also retains the primary characteristics of an M-65: a rounded collar, dual-closure zip-front covered by a snap-up fly, four pockets with pointed flaps (each closing with a concealed snap), snap-down shoulder epaulets, and bi-swing pleats behind the shoulders. Harry keeps the ends of the sleeves self-cuffed over his wrists.

Harry arrives at Sally’s apartment wearing a black wool cable-knit fisherman’s-style sweater that shares many details—including its cozily oversized fit—with his famous cream-colored sweater worn earlier. The Aran-style cable patterns are even the same, with thick rope twist patterns stretching down the sides and center, separated by narrower purl-knit channels. The rounded and raised mock-neck is narrowly ribbed, matching the cuffs.

When a crying Sally gets tears (and likely snot) on the sweater, he nonchalantly jokes that she shouldn’t worry: “Go ahead, it’s not one of my favorites anyway.”

In her retrospetive GQ ranking of all 32 of Billy Crystal’s tracked costume changes, Sophia Benoit calls out the fact that Harry again wears this same striped ringer T-shirt layered under his inside-out sweatshirt on New Year’s Eve: “I can’t be the only one who thinks it might be A Thing that he’s wearing the shirt he wore over to her house when they hooked up because it reminds him of her!” (For what it’s worth, this outfit fares well on Sophia’s ranking at #12, as she notes that “Black doesn’t read well on screen, so you’re just going to have to trust me that this luxurious sweater is a spicy meatball of a look. Harry understands classics and layering like no other leading man in recent memory.”)

This short-sleeved tee is horizontally striped in black and gray, with black ringers around the crew-neck and sleeve-ends.

Harry tucks the T-shirt into his usual mid-blue denim Levi’s jeans, styled with the conventional five-pocket arrangement across the front and back.  He holds them up with a glossy brown braided leather belt that closes through a gold-toned single-prong squared buckle. Especially appropriate given the [initially] casual nature of his visit, Harry wears his usual Nike Rake AC sneakers, crafted with all-white leather uppers save for its blue collar and blue swoosh logos over the top of each heel.

He had first worn this jacket a year earlier at a Giants game, where a then-bearded Harry glumly tells his best friend Jess (Bruno Kirby) the details of his divorce from Helen. Harry is dressed cozily for the fall-to-winter chill of football season, although his black-and-gray crew-neck sweater, burgundy scarf, and black leather gloves may be dressier than many are used to seeing in the stands of an NFL game.

Jess: Marriages don’t break up on account of infidelity. It’s just a symptom that something else is wrong.
Harry: Oh really? Well, that “symptom” is fucking my wife.

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How to Get the Look

This may be a quintessential Harry Burns look, tastefully layering a military-style jacket—in this case a field jacket—over a cozy sweater, paired with his sporty staples of blue jeans and sneakers.

• Sage-green cotton-shell civilian M-65-style field jacket with round collar, zip/snap-closure front, shoulder epaulets, four patch pockets with hidden-snap pointed flaps, and bi-swing shoulder pleats
• Black wool cable-knit mock-neck sweater with ribbed neck and cuffs
• Black-and-gray horizontal-striped cotton short-sleeved ringer T-shirt
• Blue denim Levi’s five-pocket jeans
• Brown braided leather belt with gold-toned single-prong squared buckle
• White leather Nike Rake AC sneakers

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Do Yourself a Favor and…

Check out the movie.