The Sopranos: The Don Wearing Shorts

James Gandolfini as Tony Soprano on The Sopranos (Episode 2.01: “Guy Walks into a Psychiatrist’s Office…”)


James Gandolfini as Tony Soprano, New Jersey mob boss

North Caldwell, New Jersey, Summer 1999

Series: The Sopranos
Episode: “Guy Walks into a Psychiatrist’s Office…” (Episode 2.01)
Air Date: January 16, 2000
Director: Allen Coulter
Creator: David Chase
Costume Designer: Juliet Polcsa


“A Don doesn’t wear shorts.” Yeah, yeah, every fan of The Sopranos knows the story… but after the record-breaking heat last month, I think we can all agree that Tony Soprano would get a pash for that as we head into August.

The second season premiere of The Sopranos begins with the Skip striding out to the end of his driveway as usual, though he comes back not just with The Star-Ledger but also Salvatore “Big Pussy” Bonpensiero (Vincent Pastore). Puss had been one of Tony’s closest friends among his crew before he mysteriously went missing at the end of the previous season, prompting rumors that he became an informant.

Even after the return of the prodigal Pussy, Tony can’t help but to eye his friend with suspicion, even over the flames of his charcoal grill during a backyard barbecue. By that point, Puss is far from Tony’s only problem, as he’s also welcomed back his estranged sister Janice Parvati (Aida Turturro)… and all the conniving baggage that entails. Ever the instigator, Janice tries to start drama by commenting to their sister Barbara (Nicole Burdette) about their mother’s absence: “Some family reunion… the woman that bore them all barred from the premises!”

Upon learning during the cookout that Janice is already trying to block his sale of their mother’s house, Tony complains to Carmela that “I’m still a little fat kid to her!”, though even at his angriest, he still doesn’t seem ready to hear her ask about his plans on returning to therapy. It isn’t until he verges on a panic attack while observing Big Pussy at the party that he again contacts Dr. Melfi (Lorraine Bracco) in the hopes of resuming his treatment.

Of course, just because Tony’s ready again doesn’t mean that Dr. Melfi is. Stewing from the loss of a patient who committing suicide due to her Tony-induced unavailability, the good doctor hits back at her felonious former patient by asking “How many people have to die for your personal growth?”

What’d He Wear?

Aside from his usual assortment of gold jewelry, Tony Soprano’s checked sports shirt, shorts, and boat shoes illustrate more of a typical suburban dad aesthetic, without the bold silk prints or Italian knits that define much of his mafioso style. The attire recalls how Tony had dressed for a similar context toward the end of the first episode during his son’s birthday cookout a year prior.

In “Guy Walks into a Psychiatrist’s Office…”, Tony wears a lightweight puckered cotton short-sleeved shirt with a light stone-gray overcheck against a black-and-gray buffalo-checked ground. The overchecks consist of one triple-striped check that intersects against the lightest gray squares and a white double-striped check that intersects over the black squares.

The shirt has a flat casual collar known as a “camp collar” or “loop collar” (for the self-loop on the left side that presumably connects to a top button under the right collar leaf), a breast pocket, and six smoke-gray plastic buttons up the plain front (no placket), with the top few left undone to show the top of Tony’s usual white ribbed cotton sleeveless undershirt.

James Gandolfini and Vincent Pastore on The Sopranos (Episode 2.01: "Guy Walks into a Psychiatrist's Office...")

Tony’s sisters observe him at the grill, surrounded by his cronies, remarking how much the scene reminds them of their late father.

Tony dresses for the summer cookout in a set of black cotton double-pleated shorts that end above the knees.

An oft-repeated story from the production of The Sopranos involves a late-night call that James Gandolfini received between seasons, during which a mysterious man complimented his work on the series in a gravelly voice but added one piece of advice. “Listen, you’re a great actor, we like what you’re doing, but you got to know one thing: A don never wears shorts,” the actor was told, as later relayed by his co-star Michael Imperioli (per The Daily Mail.)  Although Gandolfini was understandably creeped out by the invasion of privacy, the incident was relayed in the fourth season premiere when New York mob boss Carmine Lupertazzi Sr. (Tony Lip) pulls Tony aside to share the same tip: “John said he went to a cookout at your house… a Don doesn’t wear shorts.”

Despite the shadowy suggestions of a real-life wiseguy and Carmine’s in-universe comments, Tony remains undeterred and continues to wear shorts for his at-home cookouts as seen in later episodes like “Marco Polo” (Episode 5.08), proving that a Don wears whatever the hell he wants.

James Gandolfini as Tony Soprano on The Sopranos (Episode 2.01: "Guy Walks into a Psychiatrist's Office...")

Though he’s not at the helm of the Stugots, Tony benefits from the casual comfort of boat shoes. Also known as “deck shoes”, this design emerged from outdoorsman Paul A. Sperry’s development of siped soles in the 1930s, inspired by his dogs’ grooved paws. With their herringbone-cut non-skid soles, Sperry Top-Siders became the must-have shoes for 20th century boatsmen before they strolled inland as a “crucial element” of 1980s yuppie style, according to the cover of The Official Preppy Handbook. By the start of the 21st century, boat shoes were standardized as a staple for men (and, to some extent, women) seeking comfortable yet presentable footwear in warm weather.

Tony’s deck shoes have brown leather uppers, styled with the requisite moc-toe and 360-degree lacing system.

James Gandolfini as Tony Soprano on The Sopranos (Episode 2.01: "Guy Walks into a Psychiatrist's Office...")

Tony’s usual gold jewelry includes a necklace, a bracelet, a pair of rings, and his classic Rolex Day-Date “President”, ref. 18238. This luxury chronometer has an 18-karat yellow gold case, champagne colored-dial with day of the week across the top and a 3:00 date window, and the distinctive semi-circular three-piece “President” or “Presidential” link bracelet introduced in tandem with the Day-Date model in 1956.

James Gandolfini as Tony Soprano on The Sopranos (Episode 2.01: "Guy Walks into a Psychiatrist's Office...")

Promotional photo of James Gandolfini on set.

Suspended from Tony’s thin gold necklace is a round pendant depicting Saint Anthony, the patron saint of lost items to Catholics like the Soprano family and evidently his namesake. He wears his gold wedding band on the ring finger of his left hand and a diamond-and-ruby bypass gold pinky ring on his right hand. Tony’s yellow-gold bracelet over his right wrist has been described by @tonysopranostyle as “a Cuban curbed link chain and an Italian Figaro link chain with a twist.”

James Gandolfini as Tony Soprano on The Sopranos (Episode 2.01: "Guy Walks into a Psychiatrist's Office...")

Is it truly a family reunion if no one has you howling with rage in the kitchen?

How to Get the Look

James Gandolfini as Tony Soprano on The Sopranos (Episode 2.01: “Guy Walks into a Psychiatrist’s Office…”)

Tony Soprano saves the bowling shirts, bold prints, and knitwear for mobbed-up functions, instead dressing for his backyard barbecue in a checked sports shirt, pleated shorts, and boat shoes that could have been found in any dad’s closet in the ’90s… unlike much of the gold jewelry.

  • Gray-and-black buffalo-check (with light stone-gray overcheck) puckered cotton short-sleeved camp shirt with loop collar, breast pocket, and plain front
  • Black cotton double-pleated knee-length shorts
  • Brown leather boat shoes
  • White ribbed cotton sleeveless undershirt
  • Rolex Day-Date “President” 18238 self-winding chronometer watch in 18-karat yellow gold with champagne-colored dial and Presidential link bracelet
  • Gold curb-chain link bracelet
  • Gold pinky ring with bypassing ruby and diamond stones
  • Gold wedding ring
  • Gold open-link chain necklace with round St. Anthony pendant

Do Yourself a Favor and…

Check out the entire series.

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