5 Queer Historical Icons and Their Most Influential Tailoring Looks

Yet throughout history, tailoring has also been used to challenge convention. Many LGBTQ+ individuals embraced tailored clothing not for it’s conformity, but as a way to question social expectations and redefine the relationship between dress and gender. By reimagining and adapting traditional tailoring, they demonstrated that tailoring could be every bit as expressive as it was formal.

Pride Month gives us a great opportunity to celebrate some of the figures who expanded the ideas behind traditional tailoring, and an influence that extends far beyond fashion history. Here are a few of our favourites…

Gladys Bentley and the White Tuxedo

Historical Context

Born in Philadelphia in 1907, Gladys Bentley became one of the most recognisable performers of the Harlem Renaissance during the 1920s and 1930s. She was a gifted blues singer and pianist, and rose to prominence in New York's thriving nightlife scene, performing regularly at queer-friendly venues such as Harry Hansberry's Clam House.

Bentley worked during a period when queer visibility was thriving within certain artistic communities in Harlem before anti-LGBT crackdowns became more widespread during the 1940s and 1950s. Racial segregation remained firmly established across the United States, but Gladys performed before racially mixed audiences and refined a public image in the entertainment industry.

The Legacy of Her Tailoring

Evening tailcoat with satin peak lapels, a welted breast pocket and heavily padded shoulders.

Traditional evening tailcoat construction, with the front quarters cut away below the waist and the rear extending into elegant swallowtail skirts.

Matching high-shine single breasted satin waistcoat featuring a deep U-shaped opening.

Stiff detachable wing-collar dress shirt paired with high-waisted trousers finished with a formal satin soldier stripe.

White top hat, dress gloves and walking cane completing the look.

Why It Was Revolutionary

The tuxedo had historically symbolised elite male privilege, but Bentley appropriated these established codes and transformed them into something entirely her own. Bentley stood over six feet tall, and used her tailoring to strengthen her authority on stage. She openly flirted with women and frequently used references to same-sex desire into her performances. Importantly, she did not present herself as a man. Instead, she created a distinctly queer form of masculinity that did not comply with traditional gender expectations.

Her white tuxedo remains one of the earliest and most influential examples of tailoring being used as a definitive form of queer expression.

David Bowie and the Life on Mars? Suit

Historical Context

Bowie’s promotional film for “Life on Mars?” was released in 1973, during his iconic Ziggy Stardust era. The influential Glam rock period actively challenged traditional ideas of masculinity, encouraging experimentation with identity and performance.

Bowie fully embraced this cultural shift, and used clothing as a medium of transformation to blur the boundaries between masculine and feminine aesthetics.

Designer and Creative Team

The suit worn in the Life on Mars? promotional film was designed by Freddie Burretti, an early collaborator of Bowies, as were many of the Ziggy Stardust era looks. Burett drew inspiration from many sources, including traditional British tailoring, Japanese fashion, London street style, theatre costume and glam rock.

The film itself was directed by renowned photographer Mick Rock, often referred to as "The Man Who Shot the Seventies" due to his iconic documentation of the decade's cultural figures.

The Suit

The styling of the suit was surprisingly restrained, despite its theatrical references, allowing the cut and proportions of the garment to take centre focus. 

Single-breasted jacket with a one-button closure.

Exaggerated peak lapels, roped shoulders and a strongly suppressed waist.

Double front darting and jetted hip pockets.

High-rise trousers with extended turn-ups that further enhanced the dramatic proportions.

Powder-blue cloth that defied expectations of traditional suiting colours.

Why It Challenged Convention

The combination of Bowie's vivid red hair, pale complexion and dramatic makeup, created a futuristic and androgynous image. The ambiguous look demonstrated that tailoring could communicate creativity, and colour was just as important a role as cut and construction.

The influence of the Life on Mars? suit continues to be felt throughout contemporary fashion, particularly gender-fluid tailoring collections.

Oscar Wilde and the Smoking Jacket

Historical Context

Oscar Wilde was one of the leading figures of the Aesthetic Movement in Victorian Britain. Wilde was a highly influential author, poet and playwright, he thoroughly advocated for art and beauty over social conventions.

His works include The Picture of Dorian Gray, The Importance of Being Earnest and essays including The Philosophy of Dress. However during his lifetime, he became almost as famous for his personal style as for his literary achievements.

Origins of the Smoking Jacket

The smoking jacket emerged during the mid-nineteenth century as a practical leisure garment, traditionally worn after formal dinners while smoking cigars or pipes. The jacket was designed to absorb tobacco odours and protect evening wear from smoke, primarily for private domestic use rather than public display.

Smoking jackets were often crafted from luxurious fabrics such as velvet, silk, brocade and quilted textiles. The jacket featured details like shawl collars, braided trim, silk facings and rich jewel tones.

Wilde's Interpretation

Wilde transformed the smoking jacket into a public statement, and often wore his jacket for public leisure rather than reserving it for private settings - this soon became part of his aesthetic identity. He often smoked for theatrical effect and was known, like many in the 19th century, not to inhale.

By wearing smoking jackets outside of their traditional context, Wilde made a practical leisure garment into his own symbol of individuality. Wilde frequently wore velvet jackets, decorative waistcoats, silk cravats and neckties, embracing clothing as a form of artistic expression. On the opening night of Lady Windermere's Fan (1892), Wilde popularised the green carnation - this then became a discreet symbol of homosexuality and dandyism. 

Frida Kahlo's 1927 Suit Portrait

Historical Context

Frida Kahlo is widely regarded as one of the most influential artists of the twentieth century. Best known for her self-portraits, she explored themes of identity, gender, disability and cultural heritage throughout her work.

An image of her early life in a family portrait taken in 1927, was taken when she was only nineteen years old. This image was influential in the fact that it was captured before her international recognition, and after the bus accident that would permanently affect her health.

The Photographer

The image was taken by her father, Guillermo Kahlo, a professional photographer who emigrated from Germany to Mexico. Photography was significant within the Kahlo household, and Guillermo encouraged Frida's intellectual curiosity and independence from an early age. His influence remained an important part of her life and artistic development.

The Outfit

While her sisters appear in conventional dresses, Frida chose to wear a tailored three-piece suit.

A tailored jacket, waistcoat, and trousers that created a traditionally masculine silhouette.

Minimal padding and classic notch lapels gave the jacket a relaxed yet distinctly menswear-inspired appearance.

A three-button jacket and high-closing waistcoat, period-correct tailoring details that created a conservative look.

A narrow tie, and high waisted trousers, establishing a longer leg line.

A straight silhouette, minimising emphasis on the bust and waist.

Why This Matters

The photograph's significance lies partly in its intimate setting, and was not worn for public image.The image reflects Frida's strong identification with her father, while providing early evidence of her willingness to experiment with both masculine and feminine modes of dress. It also demonstrates that the Tehuana-inspired clothing, for which she later became famous, represented only one aspect of her personal style.

Throughout her life, Kahlo moved fluidly between different forms of self-presentation. This exploration of gender through clothing resurfaced in her 1940 painting Self-Portrait with Cropped Hair, where she again depicted herself wearing a suit.

Marlene Dietrich and the 'Morocco' Tuxedo

Historical Context

Dietrich was a German-born actress and singer, and became one of Hollywood's biggest stars during the 1930s. Alongside her success on screen, she developed a reputation for challenging social conventions through her approach to dress.Her influence on tailoring remains profound, particularly in relation to women's adoption of traditionally masculine clothing.

Key Moment: Morocco (1930)

Dietrich's most famous tailoring moment arrived in Morocco (1930), directed by Josef von Sternberg, (1930) is a romantic drama about a cabaret singer who falls in love with a French Legionnaire. In a memorable scene, she appears on stage wearing a tuxedo and silk top hat,  before famously kissing a female audience member. The sequence remains one of the most iconic queer moments of early Hollywood history.

Her Tuxedo Style

A silk top hat, worn slightly at the back of the head, producing a relaxed and elegant finish.

A tailcoat featuring strong shoulders, broad proportions, and deeply cut front quarters that swept away from the waist.

Suppressed waist and long tails, creating a dramatic and elongated silhouette.

Peak lapels, a bib-front shirt and wing collar - traditional white-tie details that reinforced the outfit's connection to classic menswear tailoring.

Beyond the Film

Dietrich's commitment to her tailoring extended far beyond Morocco. She regularly wore tuxedos at film premieres, in publicity photographs, during nightclub performances, as well as at social engagements. Unlike many performers who treated menswear as a costume, Dietrich incorporated tailoring into her everyday public image.

Why It Was Revolutionary

Women wearing trousers remained controversial throughout much of the early twentieth century, with some cities actively discouraging or restricting women from wearing trousers in public. Dietrich reportedly refused requests to change her clothing while visiting Paris, supporting her reputation for independence.

Perhaps most importantly, she demonstrated that tailoring could be both glamorous and assertive on women. Dietrich treated the tuxedo as serious dress rather than novelty attire, and in-turn helped to redefine the possibilities of womenswear.

Fashion historians frequently identify Dietrich as a direct predecessor to Yves Saint Laurent's revolutionary Le Smoking suit of 1966, securing her place in the history of tailoring.

The Power of Tailoring as Self-Expression

Although these figures are separated by different generations and backgrounds, they shared a common belief in the power of clothing to communicate self expression,

Gladys Bentley challenged the conventions of race, gender and sexuality through her public persona and masculine aligned tailoring. 

David Bowie used tailoring as a tool for transformation and gender ambiguity. 

Oscar Wilde rejected conventional Victorian dress norms, and embraced the ideals of the Aesthetic Movement.


Frida Kahlo challenged expectations surrounding gender, femininity, and identity through her personal style.

Marlene Dietrich blurred the boundaries between menswear and womenswear, also helping make women's tailoring glamorous and desirable.

Together, they expanded ideas about who could wear tailored clothing and what it could communicate. The influence of these figures reminds us that tailoring has never been solely about status or tradition, and offers an opportunity for personal expression and self-expression. 

Pride Month provides an opportunity to recognise these contributions to LGBTQ+ history,  as well as fashion itself. Their legacy has continued into modern tailoring,and  encourages  a more inclusive understanding of style.