Key Takeaways:
- Gordon Gekko's style from Wall Street (1987) continues to influence men's fashion decades later
- Contrast collar shirts paired with braces became signature elements of 1980s power dressing
- The horizontal striped shirt with vertical collar represents Gekko's "new money" approach to style
- Double-breasted sports jackets offer versatile options for sophisticated cocktail attire
- Custom tailoring details like turn-back cuffs and drape cuts defined Gekko's distinctive look
- Modern interpretations of Wall Street style focus on fit, proportion, and selective statement pieces
Introduction: The Lasting Impact of Wall Street's Fashion Legacy
The 1987 Oliver Stone film "Wall Street" didn't just influence financial culture—it fundamentally transformed men's fashion for decades to come. Few films have had such a profound and lasting impact on how men dress in professional settings. The character of Gordon Gekko, masterfully portrayed by Michael Douglas, created what we now recognize as the quintessential power dressing aesthetic of the 1980s. What makes this style so fascinating? Why do we still reference Gordon Gekko's wardrobe choices nearly four decades later when discussing men's tailoring and corporate fashion?
The film's costume choices weren't merely decorative—they communicated status, ambition, and a certain ruthless elegance that defined the era's corporate raiders. From the iconic contrast collar shirts to bold suspenders and impeccably tailored suits, each element was carefully selected to convey the character's new money sensibilities and outsider status within the financial establishment.
Are you curious about how these iconic looks were constructed? Do you wonder which elements of Gordon Gekko style have stood the test of time? This detailed analysis will break down the key components of Wall Street fashion that continue to influence modern menswear, examining how this distinctive 1980s men's fashion approach can be adapted for today's gentleman.
Gordon Gekko's Iconic Power Dressing: The Braces and Contrast Collar Combination
The first meeting between young stockbroker Bud Fox (Charlie Sheen) and corporate raider Gordon Gekko (Michael Douglas) introduces us to what would become one of the most influential looks in men's fashion history. As Gekko strides confidently behind his power desk, several key elements immediately establish his dominant presence and unique style approach.
Most striking are Gekko's exposed braces (suspenders), which became an instant fashion phenomenon following the film's release. These weren't ordinary store-bought varieties—Gekko sports authentic Albert Thurston braces, featuring thick ribbons with bold stripes and proper button-on ends. What's particularly interesting is the practical origin behind this style choice. Michael Douglas's slim physique, particularly his narrow hips, required braces to ensure his trousers draped properly. This practical necessity transformed into perhaps the most recognizable element of 1980s power dressing.
The contrast white collar on a blue shirt body forms another cornerstone of the Gekko look. This style choice was actually on the verge of falling out of fashion when the film premiered, yet Gekko's character revitalized it completely. The stark white collar frames his face while projecting authority and sophistication, distinguishing him from his more conservatively dressed colleagues and subordinates.
His distinctive look is completed with rolled-up sleeves, creating a hands-on impression that suggests Gekko is both a thinker and a doer. The slicked-back hair further frames his face, focusing attention on his expressions and commands. His silk medallion print tie, secured with a slightly angled tie bar positioned lower than was typical, adds another layer of calculated precision to his appearance.
How does Gekko's look contrast with the other Wall Street professionals in the film? While Bud Fox and his colleagues adhere to more conservative corporate American standards—button-down shirts, single cuffs, darker ties, and brownish-gray suits—Gekko's fresh approach sets him apart as someone who follows his own rules rather than conforming to established Wall Street dress codes.
Horizontal Stripes and New Money Style: Analyzing Gekko's Bespoke Shirts
When Gordon Gekko takes Bud Fox to lunch, he wears a distinctive shirt that perfectly expresses his character's complex relationship with wealth and status. What makes this particular shirt so fascinating is its historically informed yet rule-breaking design—featuring a horizontal striped body paired with a vertical striped collar. This unconventional combination serves as a visual metaphor for Gekko's position as a financial world outsider who has forced his way into the establishment.
Horizontal striped shirts have historical precedence dating back to Edwardian times, when detachable collars were common. However, Gekko's version takes this concept further with its contrasting vertical stripes on the collar that align perfectly with the collar's shape. This deliberate style choice speaks volumes about his character's psychology and social positioning.
As a self-made man with what modern observers might call "new money," Gekko embodies someone eager to broadcast his financial success. His shirt practically announces: "I can afford bespoke clothing, and I want everyone to know it." This ostentatious approach to custom tailoring reveals his character's inner conflict—simultaneously desiring acceptance from the old-money establishment while defiantly asserting his outsider status.
The shirt represents Gekko's approach to wealth display—slightly overdoing it, perhaps trying too hard by traditional standards, but carrying it off through sheer confidence and charisma. Unlike the subtle signals of old-money dressing, where quality is recognized only by those "in the know," Gekko's style choices are bold declarations of his financial power.
This tension between wanting to appear established while simultaneously rejecting establishment norms defines not just Gekko's shirts but his entire wardrobe philosophy. His clothing choices consistently walk this line between traditional tailoring and statement-making modifications that announce his presence in any room.
The Double-Breasted Sports Jacket: Gordon Gekko's Sophisticated Cocktail Attire
One of Gordon Gekko's most relevant and timeless looks appears during the beach house cocktail party scene, where he faces off with Sir Larry Wildman (Terence Stamp). His double-breasted sports jacket represents a perfect solution to the challenging middle ground between business attire and formal evening wear.
This bluish-gray jacket—likely crafted from a luxurious silk-wool gaberdine blend—features distinctive white buttons and a Kent-style roll to the bottom. Gekko pairs it with a fine-gauge navy blue polo shirt, creating an ensemble that communicates sophisticated ease while maintaining an air of authority. This combination demonstrates how to look appropriately dressed for a social occasion without resorting to black tie formality.
What makes this particular outfit so remarkable is how contemporary it feels despite being designed for a film set in the 1980s. The concept of a "third wardrobe" specifically for cocktail gatherings—beyond business suits and formal attire—was forward-thinking then and remains relevant today. Modern men continue to search for this perfect balance: clothing that signals effort and respect for the occasion without appearing overdressed.
The jacket's construction deserves special attention. Its generous cut through the chest creates what tailors call "drape," providing comfort while maintaining a structured silhouette. This approach to tailoring accommodates movement without sacrificing shape—essential for social settings where one might be standing for extended periods.
The decision to pair this sophisticated jacket with a polo shirt rather than a traditional dress shirt shows Gekko's confidence in breaking conventions while understanding the fundamental principles of elegant dressing. The fine-gauge polo adds texture and interest while softening the formality just enough for a beach house setting.
This outfit exemplifies how Gekko's character navigates social situations—always appropriate yet distinctive, commanding attention without appearing to try too hard. It's precisely this balance that makes the look feel more relevant today than when it first appeared on screen in 1987.
Masterful Tailoring: Gekko's Prince of Wales Check Suit and Peak Lapel Details
In the scene where Gordon Gekko meets with Darien Taylor (Daryl Hannah), he showcases perhaps his most technically impressive suit—a double-breasted Prince of Wales check with a subtle pinkish-red overcheck. This exquisite piece of tailoring demonstrates Gekko's sophisticated understanding of pattern, proportion, and personal style.
The suit features what tailors call a "drape cut," characterized by fullness through the chest that creates an athletic silhouette regardless of the wearer's actual physique. Michael Douglas's naturally slim frame provides the perfect canvas for this tailoring approach, allowing the fabric to hang with elegant precision. The six-button, Kent-style double-breasted configuration—where the suit fastens at the lower button—creates a longer line that enhances Douglas's height while allowing greater freedom of movement.
Complementing this remarkable suit is a bold red and white striped shirt with a white contrast collar. This combination perfectly illustrates a practical style principle that remains valuable today: when wearing shirts with bold patterns, a white collar helps frame the face and prevents the pattern from becoming visually overwhelming. This thoughtful detail allows Gekko to incorporate color and pattern while maintaining a composed, authoritative presence.
While popular culture often reduces "Wall Street style" to double-breasted suits and red braces, true fashion enthusiasts recognize that Gekko frequently wore single-breasted suits with peak lapels. This variation offers the commanding presence of wider lapels while providing the openness and versatility of a single-breasted jacket—a sophisticated compromise that suits many modern men better than fully double-breasted designs.
Perhaps most telling about Gekko's character are the turn-back cuffs (also called "gauntlet cuffs") on his suit jacket. This archaic detail, rarely seen in contemporary ready-to-wear clothing, broadcasts his commitment to custom tailoring. Like the horizontal striped shirts discussed earlier, these cuffs announce "this is bespoke" to anyone knowledgeable enough to recognize them. They represent Gekko's desire to signal that he can afford the very best—a subtle yet unmistakable status symbol.
The finishing touches include a fine pink gingham shirt with a rounded white collar, worn with a tie pin or slide—details that would not look out of place on Savile Row today. This ensemble demonstrates how thoughtful tailoring transcends trends, remaining relevant decades after its creation.
How to Incorporate Wall Street Style into Modern Men's Fashion
The enduring appeal of Gordon Gekko's style lies in its confidence and attention to detail. But how can today's man integrate elements of this iconic 1980s power dressing without looking costumey or dated? The key is selecting specific components that complement contemporary sensibilities while honoring the original spirit of the look.
Start with the foundation: properly tailored suits. The most timeless aspect of Wall Street style is its emphasis on fit and proportion. Whether you opt for a Prince of Wales check pattern or a solid navy, ensure your suit features strong shoulders and a defined waist. Modern interpretations might slim down the silhouette slightly, but maintain the structured shape that communicates authority.
Contrast collar shirts offer perhaps the easiest entry point into Gekko-inspired style. This distinctive detail works particularly well in business settings, creating visual interest while remaining professional. For a contemporary approach, consider more subtle color combinations—a light blue shirt with white collar rather than bold stripes—and pair with a simple knot tie in a muted pattern or solid color.
Braces (suspenders) remain the most recognizable element of the Wall Street look. If you're bold enough to embrace them, follow Gekko's example by investing in quality. Button-on styles provide both functionality and authenticity. Remember that braces work best with trousers specifically cut for them—slightly higher-waisted with side adjusters rather than belt loops.
For less formal occasions, the double-breasted sports jacket offers tremendous versatility. Modern iterations often feature softer construction and lighter fabrics than their 1980s counterparts, making them more comfortable while retaining the commanding presence. Pair with dark trousers and a fine-gauge polo or lightweight sweater for a sophisticated yet relaxed impression.
Peak lapels on single-breasted suits provide another way to reference the Gekko aesthetic without fully committing to double-breasted styles. This subtle detail adds character to otherwise conservative business attire and creates a stronger shoulder line for most body types.
When adopting elements of this style, maintain balance by limiting yourself to one or two signature pieces rather than recreating entire outfits. A modern suit with a contrast collar shirt makes a strong impression without the need for additional 1980s references. Similarly, a contemporary business suit worn with quality braces keeps the look grounded in the present while nodding to the past.
The most important aspect to capture isn't specific garments but the underlying confidence they represent. Gordon Gekko's clothing worked because it expressed his character's absolute certainty in his own judgment—even when that judgment defied convention.
Custom Tailoring Touches That Defined the Gordon Gekko Look
The true sophistication of Gordon Gekko's wardrobe lies in its bespoke details—subtle elements that distinguish custom tailoring from off-the-rack alternatives. Understanding these refinements provides insight into how the character used clothing to project power and exclusivity.
Turn-back cuffs (or gauntlet cuffs) represent one of the most distinctive custom details in Gekko's suits. These decorative sleeve endings, featuring a small flap that appears to fold back on itself, originated in functional military uniforms but evolved into purely aesthetic elements in civilian tailoring. In the context of 1980s Wall Street, they served as a clear signal that Gekko's suits weren't purchased but commissioned—a subtle indication of wealth that only those "in the know" would recognize.
The precise fit of Gekko's clothing demonstrates another hallmark of bespoke tailoring. Notice how his jackets drape cleanly across the shoulders without bunching or stretching, while providing fullness through the chest. This "drape cut" creates an athletic silhouette regardless of the wearer's actual build—a technique pioneered by London tailors in the early 20th century. Michael Douglas's naturally slim physique allows these suits to hang perfectly, with trouser breaks that just touch the shoe without excessive fabric pooling.
Pattern matching represents yet another sign of quality tailoring throughout Gekko's wardrobe. On his checked and striped suits, patterns align precisely at the seams—a labor-intensive detail impossible to achieve in mass production. This attention to pattern continuity across pockets, lapels, and shoulders demonstrates the hours of handwork invested in each garment.
Button stance—the position where jackets fasten across the torso—plays a crucial role in Gekko's silhouette. His suits typically feature slightly lower button positioning than was standard, creating a longer lapel line that enhances his stature and provides greater lapel display. This seemingly minor adjustment significantly impacts the overall impression of his suits.
Hand-stitched details appear throughout Gekko's clothing, from the pick stitching along lapel edges to the hand-sewn buttonholes. These subtleties broadcast quality workmanship while providing practical benefits—hand-attached linings move more naturally with the body, while hand-finished edges maintain their shape longer than machine-finished alternatives.
The relationship between Gekko's shirts and suits reveals another custom tailoring advantage. His collar shapes and proportions perfectly complement his face and harmonize with his jacket lapels. This balance of elements is nearly impossible to achieve with separate off-the-rack purchases, highlighting the cohesive nature of a fully bespoke wardrobe.
Understanding these details helps explain why Gordon Gekko's style continues to fascinate fashion enthusiasts decades later. Beyond mere flashiness, his wardrobe demonstrates an understanding of tailoring traditions while simultaneously subverting them to create something distinctive and personal.
Westwood Hart's Modern Take on 1980s Power Dressing
At Westwood Hart, we understand the enduring appeal of Wall Street's power dressing aesthetic while recognizing how contemporary gentlemen can adapt these principles for today's professional environments. Our approach honors the confidence and precision of Gordon Gekko's style while refining it for modern sensibilities.
Our custom tailoring process begins with the same foundation that made Gekko's wardrobe so impactful—exceptional fit and proportion. We create suits with strong, defined shoulders and a shaped waist that creates a commanding presence without the exaggerated silhouettes of the 1980s. This balance between structure and comfort allows our clients to project authority while maintaining freedom of movement throughout demanding workdays.
The double-breasted suit, so iconic in Wall Street's fashion legacy, remains a cornerstone of our business suits collection. Our contemporary interpretation features slightly narrower lapels and a more moderate button stance than their 1980s counterparts, creating a timeless silhouette that works equally well in boardrooms and social settings. For clients seeking a more versatile option, our single-breasted suits with peak lapels offer the same authoritative presence with additional versatility.
Pattern selection provides another way we reference Wall Street's influence while keeping designs firmly in the present. Our Prince of Wales check suits offer subtle complexity and visual interest without overwhelming the wearer, while our pinstripe collection includes options ranging from bold statements to barely-there shadow stripes, allowing clients to calibrate precisely how much "power" they wish to project.
Contrast collar shirts feature prominently in our collection, offering perhaps the most accessible entry point into Gekko-inspired style. Our designs pair white collars with bodies in various colors and patterns, from classic blue to more contemporary options. This detail frames the face effectively while providing a perfect backdrop for our selection of printed and woven silk ties.
For those bold enough to embrace the most recognizable element of Wall Street style, we offer guidance on incorporating quality braces into a modern wardrobe. Our trousers can be crafted with proper brace buttons and a higher rise that complements this traditional accessory. Many clients find that braces not only create a distinctive look but also provide superior comfort compared to belts.
We particularly pride ourselves on our "third wardrobe" options—sophisticated yet relaxed attire for situations between business and formal occasions. Our sports jacket collection includes double-breasted options in lightweight fabrics that pair beautifully with fine-gauge knitwear or casual shirting, creating the perfect balance for cocktail gatherings and upscale social events.
Through our online configurator, you can design custom suits, sports coats, and trousers that incorporate these Wall Street-inspired elements while remaining thoroughly modern. Whether you're drawn to the authoritative presence of peak lapels, the sophisticated detail of turn-back cuffs, or the distinctive look of contrast collars, we can help you create garments that command attention while expressing your personal style.
Frequently Asked Questions about Wall Street Fashion
What made Gordon Gekko's style in Wall Street so influential?
Gordon Gekko's style combined traditional tailoring principles with bold statement pieces that projected power and confidence. The character arrived at a pivotal cultural moment when business attire was evolving, and his distinctive wardrobe—featuring contrast collar shirts, exposed braces, and impeccably tailored suits—provided a template for ambitious professionals. Unlike the conservative corporate uniform of the time, Gekko's clothing communicated individuality and success while remaining within the bounds of business appropriateness.
Were Gordon Gekko's fashion choices historically accurate for 1980s Wall Street?
While somewhat exaggerated for dramatic effect, Gekko's wardrobe captured genuine elements of 1980s financial district style. The film's costume designers incorporated authentic period details like contrast collars and bold accessories while emphasizing the character's nouveau riche sensibilities through slightly ostentatious custom details. Real Wall Street professionals of the era did embrace power dressing, though perhaps with more restraint than Gekko's character displayed.
What is the difference between Gordon Gekko's style and Bud Fox's style in the film?
Bud Fox (Charlie Sheen) initially dresses in conservative corporate American style—button-down shirts, single cuffs, darker ties, and brownish-gray suits. His clothing represents traditional corporate conformity. As Fox falls under Gekko's influence, his wardrobe evolves to incorporate elements of his mentor's style, symbolizing his transformation. Gekko's clothing consistently breaks conventions while Fox's reflects his journey from establishment conformity to ambitious individualism.
How did Michael Douglas's physical build influence Gordon Gekko's wardrobe?
Michael Douglas's naturally slim frame, particularly his narrow hips, necessitated design choices that became signature elements of the Gekko look. The character's famous braces (suspenders) were initially incorporated for the practical purpose of helping trousers hang properly on Douglas's slim physique. Similarly, the drape cut of his suits—featuring fullness through the chest—enhanced his frame while creating the powerful silhouette that became synonymous with 1980s power dressing.
Which elements of Gordon Gekko's style are most adaptable for today's professional men?
The most timeless aspects of Gekko's style include his emphasis on precise tailoring, contrast collar shirts, and peak lapels. Modern men can incorporate these elements without appearing dated by choosing contemporary proportions and more subtle patterns. Single-breasted suits with peak lapels offer the commanding presence of Gekko's style with greater versatility, while contrast collar shirts remain a distinctive yet appropriate choice for business settings.
What fabrics and patterns were most associated with Gordon Gekko's wardrobe?
Gekko frequently wore Prince of Wales check patterns with subtle overplaid, pinstripes, and solid fabrics in blues and grays. His shirts featured bold horizontal stripes, gingham checks, and contrast white collars. These choices reflected both traditional business attire and the character's desire to stand out within the financial world, combining established patterns with distinctive color combinations and proportions.
How important were accessories to completing the Gordon Gekko look?
Accessories played a crucial role in Gekko's style, with his signature items including Albert Thurston braces, printed silk ties, and tie slides or pins. These details communicated attention to quality and a willingness to invest in the finest available options. For modern interpretations, focusing on one or two quality accessories provides a nod to the Gekko aesthetic without appearing costume-like.
What is the "third wardrobe" concept mentioned in relation to Gordon Gekko's style?
The "third wardrobe" refers to clothing appropriate for occasions between business formal and black tie—particularly cocktail gatherings and upscale social events. Gekko's double-breasted sports jacket worn at his beach house exemplifies this concept, offering sophistication without the formality of a full suit. This approach to occasional dressing remains highly relevant for today's professionals navigating various social and semi-formal events.