Tony Soprano’s Nautical Vacation Shirt in “Remember When”

James Gandolfini as Tony Soprano on The Sopranos

James Gandolfini as Tony Soprano on The Sopranos, Episode 6.15: “Remember When”


James Gandolfini as Tony Soprano, New Jersey mob boss

Miami Beach, Fall 2007

Series: The Sopranos
Episode: “Remember When” (Episode 6.15)
Air Date: April 22, 2007
Director: Phil Abraham
Creator: David Chase
Costume Designer: Juliet Polcsa


Even gangsters get to go on spring break! Of course, being gangsters, Tony Soprano’s trip to Florida with Paulie Walnuts (Tony Sirico) is less about tequila shots on the beach and more about laying low to avoid the heat after an old murder resurfaces from 1982… but the two wiseguys still get plenty of time to relax in the sun while the remaining arm of the DeMeo crime family scrambles to control any potential damage.

With their toothbrushes and respective tropical-printed shirts and white loafers packed, Tony and Paulie pile into a rented minivan for the thousand-mile road trip from Jersey to the southern tip of the Sunshine State, with a brief stop at a chain motel in Virginia that marks one of The Sopranos‘ many “before-they-were-stars” bit parts as a pre-Hamilton Lin-Manuel Miranda appears as a befuddled bellboy.

Lin-Manuel Miranda on The Sopranos

“I dunno…”

Arriving in Miami Beach, Tony and Paulie take luxurious refuge with “Beansie” Gaeta (Paul Herman), the erstwhile pizza parlor owner now using a wheelchair after he was run over by Richie Aprile (David Proval) during the second season. Even considering his mobility issues, Beansie may be the only character not enticed by the “remember when” conversations, having happily moved on to a brighter life on the beach with his wife and goomars.

Throughout it all, we see Tony’s growing frustration with the idiosyncratic Paulie Walnuts to the point where the aging capo’s carefree cackling watching a rerun of Three’s Company is enough to have the Skip considering homicide… a petty near-breaking point many can relate to, especially after spending two days in the car with someone who insists on peppering the air with inane memories, observations, and questions. (“Chevy Chase… fuck ever happened to him?”)

The tension comes to a head the following day when Tony and Paulie rent a sport fishing boat, ostensibly for a pleasure outing to celebrate Tony’s freedom after the Willie Overall hit was attributed to the late Jackie Aprile Sr., but Paulie’s personal game of “remember when” turns dark as he silently recalls the similarly set execution of their pal Pussy Bonpensiero (Vincent Pastore) at sea, not long after Beansie got an uncomfortably close look at Richie Aprile’s borrowed Ford Explorer.

James Gandolfini and Tony Sirico on The Sopranos

No longer oblivious to the dirty looks from his boss—which can often have more dire consequences than in other workplaces—Paulie works hard to overcome his anxiety stay in the Skip’s good graces aboard the Sea Vous Play, such as cooking up a rigatoni lunch for them. But Tony, despite having just hypocritically chiding that “‘remember when’ is the lowest form of conversation,” can’t help but to needle Paulie over old grievances, such as spreading the notorious Ginny Sack joke that had almost resulted in yet another Florida mob hit years earlier. The whole time, Tony can’t help but to eye the various instruments aboard the boat that he could use to rid himself of this potential threat… or mere annoyance.

The title “Remember When” suggests the reflections on the past that permeate the episode, from the obvious references to Tony’s first hit that drives their getaway to the nostalgia of our gangsters recalling foregone days: Tony waxing poetic about the days a hotel could send up steak and Scotch before the sanitized takeovers of impersonal corporate hospitality chains, Paulie’s constant reminiscing as the aging gangster clings to the glory days of his youth, and Junior’s decline into dementia as he struggles to remember much of anything.

“To face the past is to face one’s essential nature, and ask how much one has grown or changed, or will change, and the extent to which one even can,” contextualize Matt Zoller Seitz and Alan Sepinwall in The Soprano Sessions. “It seems Tony and everyone else are destined to suffer a fate worse than jail or even death: being forced to confront who they really are.”

What’d He Wear?

Tony Soprano’s daily wardrobe includes many boldly patterned shirts which could arguably qualify as “vacation shirts” for most, so we know that even a fugitive getaway to Miami Beach will likely see even louder prints. In a testament to The Sopranos‘ detail-oriented production, we see Carmela (Edie Falco) actually packing the shirt that Tony would wear on the boat with Paulie, recognizable for its unmistakable and colorful design.

Edie Falco as Carmela Soprano on The Sopranos

As Carmela packs Tony’s shirt, we get a glimpse of the Harbor Bay label—branded in white letters against a black-embroidered “HB” set against a low-contrast navy background.

My friend Gabe’s Instagram account @TonySopranoStyle identified the shirt as a product of the big-and-tall brand Harbor Bay, made of 100% rayon like many classic aloha shirts. The design is built on a multi blue-toned ground reflecting the sea and sky, broken up over the chest and under the short sleeves with the illustration of a sunset that adds warmth via the orange sky, golden sun, and brown water. The rest of the shirt is covered in an all-over print of nautical motifs like white ship’s wheels, dark blue shark fins breaking through white-tipped waves, and a dark blue large-scaled floral print down the center of the front and back.

James Gandolfini as Tony Soprano on The Sopranos

“Old Ironsides!”

The shirt has a camp collar traditionally associated with leisure-oriented casual attire, with six dark blue buttons up the plain front (no placket), which Tony wears unbuttoned at the top to show that he’s wearing one of his usual white ribbed cotton sleeveless undershirts.

James Gandolfini as Tony Soprano on The Sopranos

Tony contemplates whether or not Paulie will make it back to shore with him.

By this season, Tony had established his regular seaside kit of an aloha-style shirt with swim trunks and boat shoes, as seen when celebrating his birthday two episodes earlier in “Soprano Home Movies” (Episode 6.13). For his maritime outing with Paulie, he wears the same Nautica swimming trunks, made of dark navy polyester with wide blue and slate-gray stripes down each side. The embroidered text just ahead of the left stripes leaves no doubt to the manufacturer, branded “NAUTICA SURF” with the first word in white and the second in a low-contrasting blue. The trunks have a blue drawstring to tighten the fit at the waist and the inseam extends to mid-thigh.

James Gandolfini and Tony Sirico on The Sopranos

“You know, no offense, but you ever had yourself checked for Tourette’s? … Seriously. ‘Heh-heh, heh-heh.’ It’s like you got a tic or something.”

When Paul A. Sperry took inspiration from his dog’s paws to develop herringbone-siped soles back in the 1930s, it was expressly for the purpose to develop non-slip footwear that could keep wearers upright on wet and slippery boat decks. Over the decades to follow, Sperry Top-Siders found a substantial following both on both sea and shore, particularly among the collegiate set though they prevailed as a predominant shoe of ’80s yuppie culture, as reflected by their prominence on the cover of Lisa Birnbach’s tongue-in-cheek 1980 volume The Official Preppy Handbook.

Leave it to Tony Soprano to reserve his boat shoes—alternately known as deck shoes—to be worn only when on the deck of a boat, stepping aboard the Sea Vous Play in the same tan top-siders that he’d worn during his birthday weekend with the Bacalas. The uppers are a hybrid of full-grain leather and perforated side panels that enhance breathability—similar to the current Sperry Billfish model—following the usual moccasin-style construction with three-eyelet derby lacing and the deck shoe’s characteristic side-lacing system.

James Gandolfini as Tony Soprano on The Sopranos

Tony climbs to the Sea Vous Play‘s helm.

Rather than paring down his jewelry as he’s occasionally done at the past when he’s had maritime violence on his mind, Tony wears his full complement of gold jewelry and accessories. Around his neck, he wears his usual thin gold open-link necklace with a gold pendant depicting St. Anthony. (Note that I’d previously identified this as a St. Jerome pendant before I received a correction from BAMF Style reader Dylan Singh explaining that Tony wears the more common—and more name-appropriate—St. Anthony.)

From his right hand, his father’s gold ring with the diamond and ruby bypass-set stones shines from his pinky while his wrist is dressed with a gold bracelet that @tonysopranostyle describes as resembling “a Cuban curbed link chain and an Italian Figaro link chain with a twist.” He wears his gold wedding band on the ring finger of his left hand.

Finally, the Skip signals his leadership with an 18-karat yellow gold Rolex Day-Date “President”, so named for the signature three-piece semi-rounded link “Presidential” bracelet that was introduced in tandem with the Day-Date in the late 1950s and has been associated with the U.S. executive branch thanks to famous wearers like Lyndon Johnson. Tony wears a ref. 18238 Day-Date with a champagne gold dial, marked with the model’s signature curved day-of-the-week window across the top and a date window at the 3:00 position. (As of March 2022, you can pick up your own Rolex Day-Date President from 1999, the same year The Sopranos debuted, at FarFetch.)

James Gandolfini as Tony Soprano on The Sopranos

Rigatoni alla Paulie!

What to Imbibe

What goes better with a seagoing meal of rigatoni alla Paulie than beer? Tony’s beer remains covered by a koozie, but context clues via the contents of his and Paulie’s packed cooler suggests that he’s drinking a Heineken, as those are the only cans among the bottles of Corona and Stewart’s root beer… the latter of which was Paulie’s request.

The Sopranos

A cooler full of beer… and root beer, for Paulie, though Tony considers whether that baseball bat or knife would better serve his ultimate purposes for Paulie.

How to Get the Look

James Gandolfini as Tony Soprano on The Sopranos

James Gandolfini as Tony Soprano on The Sopranos, Episode 6.15: “Remember When”

Tony Soprano’s style may be considered too loud or gauche for some readers—particularly the vast majority of whom have no connection to organized crime—but the colorful nature and motifs of this rayon shirt in “Remember When” are appropriate for a celebratory day spent on the water, especially when worn with the decidedly functional swim trunks and deck shoes that happen to coordinate with the otherwise chaotic blues and browns of his shirt, respectively.

  • Blue multi-tone maritime-motif and orange sunset-print rayon short-sleeve shirt with camp collar, plain front, and side vents
  • Dark navy polyester swim trunks with blue and slate side stripes
  • Tan leather 3-eyelet moc-toe boat shoes with perforated side panels
  • White ribbed cotton sleeveless undershirt
  • Rolex Day-Date “President” ref. 18238 self-winding chronometer watch in 18-karat yellow gold with champagne-colored dial and Presidential link bracelet
  • Gold open-link chain bracelet
  • Gold pinky ring with ruby and diamond bypass stones
  • Gold open-link chain necklace with round St. Anthony pendant

Do Yourself a Favor and…

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