Risky Business: Tom Cruise in Donegal Tweed

Tom Cruise and Rebecca De Mornay in Risky Business (1983).

Tom Cruise and Rebecca De Mornay in Risky Business (1983). Photo by Steve Schapiro.


Tom Cruise as Joel Goodson, ambitious high school student-turned-pimp

Chicago, Fall 1983

Film: Risky Business
Release Date: August 5, 1983
Director: Paul Brickman
Costume Designer: Robert De Mora

WARNING! Spoilers ahead!


As we enter “Back to School” season, I want to look at one of the most famous cinematic intersections of style and scholastics, a dark coming-of-age comedy starring a young Tom Cruise as a high school student whose desire to compete in the modern materialistic marketplace leads to his engaging in some perilous pursuits… or Risky Business, if you will.

In addition with providing Cruise with his breakout role, Risky Business pleasantly surprised me with a more darkly satirical tone than many contemporary sex comedies, weaving in criticism of ’80s hyper-materialism and the increased pressure on younger people to succeed. Even the name of Cruise’s character—Joel Goodson—implies the innate demand placed on our teenage hero by his well-intended, if oblivious, parents to follow their own examples: go to Princeton, make money, and raise a family in the affluent suburbs.

Joel’s more laidback pal Miles (Curtis Armstrong) notes his friend running the risk of burning out and offers some advice:

Sometimes you gotta say “What the fuck”, make your move. Joel, every now and then, saying “What the fuck” brings freedom. Freedom brings opportunity, opportunity makes your future. So your parents are going out of town. You got the place all to yourself…

With his parents abroad, Joel has the run of their North Shore house, immediately treating himself to TV dinners, his father’s Scotch (drowned in Coca-Cola), and some Bob Seger tunes. As Joel’s desire to hasten his sense of adult sophistication intensifies, he also retains the services of an escort, Lana (Rebecca De Mornay). The young duo’s financial entanglements evolve into more personal territory as Joel becomes reluctantly engaged in a struggle against Lana’s dangerous pimp, Guido (Joe “Joey Pants” Pantoliano).

Joel’s own stakes soar when he accidentally submerges his father’s prized Porsche 928 into Lake Michigan. Facing astronomical repair costs and armed with a beautiful, well-connected prostitute, Joel lands on the best option available to him: turning his parents’ home into a brothel during an all-night party to raise the funds that will get the car fixed.

What’d He Wear?

Risky Business‘ most iconic costume-related moment would arguably be Cruise sliding across the hardwood floor in red-striped OCBD, whitey-tightys, and tube socks set to Seger’s “Old Time Rock and Roll”, but as far as actual style, I would argue the most significant or memorable fashion moment would be Joel fulfilling his persona as the most celebrated pimp of the suburbs, dressing down his tweed sport jacket with T-shirt, jeans, and—when the moment’s right—his Ray-Ban Wayfarers.

Identifiable as Donegal tweed by the bright flecks of color irregularly woven against the dark gray woolen ground, the single-breasted jacket has notch lapels with sporty welts along the edges, rolling down to a two-button front. The jacket also boasts a welted breast pocket, straight flapped hip pockets, a long single vent and three buttons on the cuff of each sleeve.

Tom Cruise as Joel Goodson in Risky Business (1983)

Ray-Bans, Dairy Queen, and Marlboros: the three ingredients to success as a teenage pimp in early ’80s Chicago.

When we first see Joel’s tweed jacket, he and Miles are anxiously seated in the lobby of Chicago’s Drake Hotel, having tracked down Lana after she lifted the Goodson family’s prized Steuben glass egg in lieu of the $300 that Joel owed her for their night together. Up through this point in the story, Joel’s style has felt like a manifestation of his Princeton ambitions, and he arguably looks the part wearing his tweed jacket with the more traditionally prep rig of a blue oxford-cloth shirt, striped tie, and slacks.

Joel’s shirt is constructed in a blue and white woven oxford cotton that presents a rich light blue finish, detailed with the button-down collar that had been an Ivy favorite since the early days of the 20th century when then-Brooks Brothers president John E. Brooks introduced his “Polo” shirt, inspired by the fastened-down collars of English polo players. The shirt also has a front placket and rounded barrel cuffs, each closing with the mother-of-pearl buttons matching those on the collar.

Tom Cruise as Joel Goodson in Risky Business (1983)

Joel dresses in his trad finest when flagging down Lana at the Drake Hotel.

Joel’s red silk tie has closely spaced shadowed beige, dark navy, and pale blue stripes, following the American “downhill” direction of right shoulder-to-left hip.

His gray wool flat front trousers are held up by a dark leather belt, with plain-hemmed bottoms that break cleanly over his dark brown leather lace-up shoes.

Tom Cruise as Joel Goodson in Risky Business (1983)

Joel and Miles are each clad in gray sports coats for their “mission” to the Drake, though Joel would soon appropriate Mr. “What the Fuck”‘s more laidback approach that pairs the jacket with a dark T-shirt and jeans rather than the traditional shirt, tie, and slacks.

Tom Cruise as Joel Goodson in Risky Business (1983)

Promotional shot of Tom Cruise for Risky Business, photographed by Steve Schapiro.

Considerably later, Joel and Miles have aligned with Lana, who agrees to recruit her fellow filles de joie for the bacchanal to raise money for the totaled Porsche. Joel breaks from his usual Ivy-inspired wardrobe for the party, which itself deviates in unexpected directions from his impromptu interview with a Princeton recruiter to his late-night tryst with Lana on the L train.

By swapping out his usual button-down, polo shirt, or sweater for the plain black T-shirt and jeans that recalls James Dean more than Dean Acheson, Joel indicates that he’s aware of how much his image correlates to his ambitions. Tonight, he’s not the overachieving student with an Ivy League future, he’s a cool, successful entrepreneur in a dangerous field.

Of course, we see Joel’s posturing for what it is, and we grow increasingly aware of his attempts to project this new “bad boy” image that submerges his layers of desperation and insecurity. His Joel the Pimp persona—complete with those famous Ray-Bans worn at night, and inside!—acts aloof during his conversation with the Princeton recruiter… but his almost immediate regret reminds us that this swaggering, shades-wearing wannabe lothario is all just an act. The next day, Joel slowly starts rebuilding his image with a tame sweater and boat shoes, working his way back to the checked OCBD, dark Shetland, and corduroys as he resumes his preordained path toward the suburban ideal of success.

Tom Cruise as Joel Goodson in Risky Business (1983)

With his change of wardrobe (and Lana’s influence), Joel transforms from the “good son” too nervous to call an escort into a rebellious “bad boy” who has sex on public transportation.

Joel leaves his OCBDs, Shetland sweaters, and Princeton sweatshirts in the closet for the party, dressing the part of a ’50s-era rebel in his plain black cotton T-shirt. He wears the crew-neck, short-sleeved pocket T tucked into his jeans.

Tom Cruise as Joel Goodson in Risky Business (1983)

Promotional shot of Tom Cruise for Risky Business, photographed by Steve Schapiro.

He also establishes a clear departure from his clean-cut preppy image by completing his look with a set of black acetate-framed Ray-Ban Wayfarer sunglasses which instantly recall Risky Business for many, even almost 40 years later.

Ray-Ban launched the Wayfarer in 1952, its bold trapezoidal frame becoming quickly emblematic in an era that celebrated sharp tail fins. Initially embraced by celebrities, Wayfarers gradually fell out of fashion by the ’70s. Perhaps noticing the small but positive impression made on sales after they were featured in The Blues Brothers, Ray-Ban launched a major product placement deal to feature their eyewear across the most stylish productions of the ’80s.

Risky Business was the first of Tom Cruise’s unofficial “Ray-Ban trilogy” through the ’80s, as Joel Goodson’s Wayfarers—featured in the first shot of the movie as well as significant placement on promotional art—revitalized interest in the then-retro style, resulting in a 50% increase in Wayfarer sales, according to Brands & Films.

Three years later, Cruise was again tapped as Ray-Ban’s cinematic ambassador when Pete “Maverick” Mitchell and his fellow Navy fliers fulfilled their need for speed while sporting Ray-Ban Aviators in Top Gun. After a brief foray into Persol territory in Cocktail, Cruise once again represented Ray-Ban when he wore their browline-framed Clubmaster model during his road trip with Dustin Hoffman in Rain Man. (Interestingly, Hoffman’s performance as Benjamin Braddock in The Graduate could arguably be called a spiritual predecessor of Joel Goodson.)

Described in the Heritage Auctions listing as “possibly the most famous sunglasses ever to appear on the big screen,” Cruise’s screen-worn Wayfarers from Risky Business were sold at auction in December 2019. The classic Wayfarer style can also be purchased new via Amazon or Ray-Ban.

Tom Cruise as Joel Goodson in Risky Business (1983)

What do you notice first, the Ray-Bans or the physics-defying degree of Tom Cruise’s chortle?

To some, tailored jackets like sports coats and blazers have no business being worn with denim, but I appreciate how Joel appropriates his tweed jacket to add a touch of class to his T-shirt and jeans. The jeans are his usual blue denim Levi’s, with a button fly that suggests the classic 501 Original Fit. (My most significant criticism would be that, with his T-shirt tucked in, the jeans worn sans belt looks incomplete.)

Tom Cruise as Joel Goodson in Risky Business (1983)

Miles and Joel evidently adopted gray sport jackets, crew-neck shirts, and jeans as their unofficial uniform as party hosts.

Joel wears his favorite white leather Nike Cortez sneakers, detailed with blue “swoosh” sides and flat white laces through the seven sets of eyelets. Designed by Nike co-founder and Olympian track coach Bill Bowerman, the Cortez debuted in 1972 and quickly gained notice as the favored running shoe for many American athletes competing in that year’s Summer Olympics. The Cortez quickly earned a reputation for balancing comfort, durability, and performance, contributing greatly to Nike’s early success and undergoing several redesigns—including the current Cortez model—in the nearly 50 years since its introduction.

Tom Cruise as Joel Goodson in Risky Business (1983)

A similar approach to dressing would reappear nearly 25 years later on Californication as David Duchovny’s Hank Moody—interestingly, an avowed Tom Cruise hater—sports a pair of Nike Cortez sneakers with his everyday sports coat, black T-shirt, and jeans in the first season episode “Absinthe Makes the Heart Grow Fonder”.

How to Get the Look

Tom Cruise as Joel Goodson in Risky Business (1983)

Tom Cruise as Joel Goodson in Risky Business (1983)

Sunglasses at night—even iconic frames like Ray-Ban Wayfarers—may be pushing it, but students returning to school and looking to up their style game could take a few pointers from Joel Goodson’s party night attire, keeping things youthful in his plain dark T-shirt, jeans, and classic sneakers but layering with a sophisticated sports coat that doesn’t threaten to age its wearer, especially one that feels the need… the need for tweed.

  • Dark gray mixed Donegal tweed single-breasted 2-button sport jacket with swelled-edge notch lapels, welted breast pocket, straight flapped hip pockets, 3-button cuffs, and long single vent
  • Black cotton crew-neck short-sleeve T-shirt with pocket
    • Similar available via Amazon
  • Blue denim Levi’s 501 Original Fit button-fly jeans
  • White leather Nike Cortez sneakers with navy “swoosh” logos
  • Black acetate-framed Ray-Ban Wayfarer sunglasses

Do Yourself a Favor and…

Check out the movie.

As one of the biggest hits of the ’80s, it would have made aspiring businessmen Joel and Miles proud of its $63.5 million box office figures, nearly a 1,000% increase over its mere $6.5 million budget.

The Quote

All I’m saying is… walk like a man.


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