September has always been a month of transition. It is the moment when fashion resets, when new beginnings are imagined, and when magazines release their most ambitious issues of the year. In 1999, as the century came to a close, ESSENCE gave its readers a September to remember.
The cover featured Halle Berry styled in a hooded catsuit with marine-blue eyeshadow that shimmered like the future itself. Beneath the playful description of the shot as “hot, hot, hot” was something deeper: a declaration that Black women belonged at the center of fashion’s biggest conversation.
This was not just another glossy portrait. It was a cultural statement. Halle Berry’s September 1999 cover arrived at the threshold of the new millennium, symbolizing both the beauty of the moment and the promise of what was to come. To understand its power, we need to revisit what was happening in fashion, in culture, and in the lives of Black women at the time.
The late 1990s were saturated with what we now call Y2K aesthetics. Metallic fabrics, bold makeup choices, high-shine textures, and futuristic silhouettes dominated runways. Designers like Jean Paul Gaultier, Thierry Mugler, and Dolce & Gabbana were experimenting with sculptural, body-conscious fashion that felt like a preview of the new millennium.
Against this backdrop, Halle Berry’s catsuit cover made perfect sense. It spoke directly to the trends of the moment while elevating them through her own charisma. Her blue eyeshadow, often cited as a makeup risk at the time, mirrored the iridescent, cyber-inspired palettes that would define the early 2000s.
For Black women readers, the cover was an invitation to imagine themselves as part of this futuristic vision. Too often, fashion magazines presented a very narrow idea of beauty. ESSENCE, by contrast, consistently placed Black women in glamorous, trendsetting roles. In September 1999, the choice to dress Halle Berry in a look that could have come straight off a Paris runway underscored that Black women were not only part of the story of fashion, they were leading it.
By 1999, Halle Berry had already proven herself in Hollywood, but her career was about to reach another level. She had delivered memorable performances in films like Boomerang (1992), The Flintstones (1994), and Bulworth (1998). She had also earned respect for taking on the television role of Dorothy Dandridge in an HBO biopic that same year, a performance that would win her both an Emmy and a Golden Globe.
The ESSENCE cover arrived at a moment of convergence. Berry was not only recognized as one of the most beautiful women in the world, she was also showing that she had the acting talent to take on serious, history-making roles. Within two years, she would win the Academy Award for Monster’s Ball, becoming the first Black woman to win Best Actress.
In this sense, the September 1999 cover was prophetic. It captured her right before the world caught up with her full power. For ESSENCE readers, many of whom had supported her since her earliest days, the cover validated their pride. It told them: this woman is ours, and she is about to change the game.
It is important to remember how different the media landscape was in 1999. Black women did not see themselves reflected widely across magazine covers. Vogue, Elle, and Harper’s Bazaar occasionally featured Black models or celebrities, but it was far from the norm.
ESSENCE held a unique position. It was one of the few national publications where Black women were the default. The editors did not have to justify putting Halle Berry on the cover. They did not have to ask if readers would “relate” to her. They knew she was already beloved.
This distinction matters. For decades, ESSENCE operated as a corrective to the exclusions of mainstream media. When the September issue of Vogue was crowned the “fashion bible,” ESSENCE created its own equivalent, speaking directly to women who were not being served elsewhere. The September 1999 cover is part of that tradition.
Halle Berry was not alone in this cultural moment. She was part of a wider constellation of Black women who were commanding attention and reshaping industries. Angela Bassett was redefining what it meant to be a dramatic actress with gravitas. Lauryn Hill had just won five Grammys for The Miseducation of Lauryn Hill (1998). Naomi Campbell was still a dominant force in modeling. Whitney Houston was touring globally and starring in blockbuster films.
What connected these women was not just talent but visibility. The 1990s were marked by an unprecedented, though still limited, number of Black women gaining space in fashion, music, and film. ESSENCE magazine documented this cultural rise issue by issue. By giving Halle Berry the coveted September slot, the magazine acknowledged her place in this broader movement.
Though ESSENCE’s letters-to-the-editor sections from that year are not widely archived, it is easy to imagine how readers reacted. Halle Berry’s cover likely inspired admiration and validation. Here was a woman whose beauty was undeniable, styled in a way that spoke to the most cutting-edge trends of the time.
But there may also have been layered conversations. Some readers may have felt a disconnect between Halle’s futuristic styling and their own day-to-day lives. Others may have celebrated the aspirational quality of the image. ESSENCE always balanced between aspiration and relatability, and the September 1999 cover leaned heavily into the former.
In retrospect, it shows how ESSENCE was willing to push boundaries. Instead of a safe glamour portrait, the magazine gave readers a vision of a Black woman occupying a fashion-forward, almost sci-fi space. That choice, bold at the time, resonates even more now.
The hooded catsuit was more than fabric. It symbolized transformation. To put a Black woman in such a striking, almost superhero-like look in 1999 was to declare that she belonged in every space: Hollywood, fashion, even futurism.
Clothing in ESSENCE covers often carried symbolic weight. Angela Bassett’s regal styling in 1992 communicated strength. Naomi Campbell’s appearance in the early 1990s emphasized Black beauty in high fashion. Halle Berry’s 1999 cover sent a message about what the next century could hold.
It was not just about fall fashion. It was about forecasting power.
Looking beyond fashion, the fall of 1999 was a time of anticipation and anxiety. The new millennium was approaching. Y2K fears filled headlines. Technology was advancing at a rapid pace. For Black communities, the decade had seen both triumphs and setbacks: greater visibility in pop culture but ongoing structural inequalities.
ESSENCE, by choosing Halle Berry in this futuristic styling, aligned itself with the excitement of the era rather than its anxieties. The cover did not show fear of the millennium but confidence that Black women would thrive in it.
The September 1999 ESSENCE cover with Halle Berry is more than a nostalgic image. It is a cultural time capsule that captures the optimism, style, and ambition of its moment. It shows a woman on the verge of groundbreaking achievements. It shows a magazine willing to place Black women at the center of fashion’s most influential season.
Two decades later, the image remains striking. The blue eyeshadow still feels daring. The catsuit still feels ahead of its time. And Halle Berry herself remains a figure of resilience and reinvention.
When we look back at this cover, we are reminded of how far representation has come and how visionary ESSENCE was in presenting a Black woman not only as glamorous but as futuristic. In 1999, the question was whether Black women would be seen in the fashion world of the new millennium. In 2025, we know the answer.
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