Barbra Streisand’s fashion choices have sparked debate over the years. Critics argue she sometimes crosses the line of appropriateness, but the iconic star defends her bold style. She reflects on her fashion journey, reminding us that true icons don’t follow trends—they set them.
Barbra Streisand’s journey from the humble kitchens of Brooklyn to the pinnacle of global superstardom is a tale of resilience, talent, and an unerring sense of style. Born in the heart of New York, Streisand’s early life was marred by tragedy and familial challenges.
Losing her father at just 15 months old and enduring a cold relationship with her stepfather, Streisand’s formative years were far from the glitz and glamour she would later be synonymous with. Despite her mother’s discouragement from pursuing an acting career, Streisand’s spirit saw her cling to her dreams with unwavering tenacity.
Even in her teenage years, Streisand’s flair for fashion was evident. This innate sense of style, coupled with her burgeoning talent, set her on a path to stardom and sartorial acclaim. Twice named to the best-dressed list, Streisand proved that her fashion sense was as captivating as her performances.
Streisand’s early memories of singing in the stairwells of her apartment block are not just nostalgic recollections but a testament to her passion for music. The acoustics of those stairwells were her first stages, where she honed the voice that would one day echo around the world. Leaving home at 16, she juggled menial jobs while keeping a close eye on Broadway, nurturing her dream in the heart of New York’s theater district.
The turning point came in 1960, at a Manhattan gay bar’s talent competition. Her rendition of “A Sleepin’ Bee” not only captivated the audience but also marked the beginning of her meteoric rise. From that moment, Streisand’s journey from a struggling artist to a household name was set in motion.
Growing up without a father, Streisand admits in her memoir that the absence impacted her self-esteem, making her feel incomplete. But confidence came with time and experience. Streisand’s fashion evolution, chronicled in her book, reveals a woman who has always expressed herself through clothing.
From her early days wearing sweaters to her savvy thrift store shopping, she embraced a style that stood out. Her unorthodox fashion choices, like the outfit at President Bill Clinton’s inaugural gala, were not just about making a statement but challenging stereotypes about women’s multifaceted nature.
Acknowledged by Vogue editor Diana Vreeland as a fashion icon, Streisand’s wardrobe choices were ahead of their time. Her preference for high-waisted outfits and flowing fabrics wasn’t just about aesthetics, but also comfort, especially during performances.
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Growing up as a girl coming from the neighborhood of Brooklyn, Streisand was keenly aware of her “differences.” In her memoir, she reflects on this, acknowledging that she didn’t fit the conventional image of a movie star. She describes herself as having a small head, a crooked nose, a mouth that felt too big, and eyes that seemed too small, even questioning her own sex appeal.
But as Streisand aged, her views on fashion and sensuality underwent a transformation. Before celebrity stylists became a thing, Barbra Streisand had already figured out her unique style. She believed that even if she didn’t fit the typical glamorous look, she could still stand out with her own kind of cool and different style. She explained that she didn’t simply follow the prevailing fashions but was instead inspired by classic films, and artwork in museums, during her teenage years, a testament to it is Streisand’s private collection of vintage clothes, film costumes, and antique dolls.
However, Streisand chose not to hide these unique features, but rather to embrace and highlight them. In her early career, she deliberately downplayed her sexuality. Her performance attire consisted of
a blend of masculine and feminine styles, combining men’s tweeds with delicate, tie-front blouses. This distinctive approach to fashion became a part of her signature style, setting her apart in the entertainment industry.
As she became more famous, she also grew more polished and confident, along with having a bold personality. However, there were some slip-ups, like the time her glittery outfit turned see-through under the bright lights at the 1969 Oscars, which embarrassed her. She also faced some criticism for her fashion choices. For example, at an inaugural gala, she wore a pinstripe suit with a vest that showed her bosom and a skirt with a high slit. One writer didn’t like the outfit, saying it sent mixed messages.
Streisand, still bothered by this, said in an email that she thought the writer was over-analyzing her outfit. She believes it says more about the writer than she does. “Why can’t women be accomplished and attractive, strong and sensitive, intelligent and sensual?” she wondered at the time.
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Although Streisand’s career has been centered around singing and acting, her influence in the fashion world has arguably been just as integral to her success.
In a recent interview, Barbra Streisand recalled a bold idea she had pitched several years back—posing for a W magazine cover wearing just a white shirt, no pants, and showcasing her legs. Back in the early days of her career, she hesitated to express her sensuality so openly, fearing judgment.
However, with the passage of time, Streisand has adopted a more carefree attitude, stating, “Now I’m too old to care.” She expressed the idea that everyone should feel comfortable expressing themselves through their clothing, emphasizing that age shouldn’t limit or dictate what people choose to wear on any given day.
Barbra found a supportive partner in James Brolin. It all started with Streisand’s bold comment about Brolin’s shaved head at their first meeting, a moment that perfectly captures the essence of their bond. Barbra Streisand’s story about her first date with James Brolin, shared on The Tonight Show in 2021, paints a really down-to-earth picture of their relationship.
It was a blind date, and Streisand was so shy she initially hung out with the kids at the house to avoid the awkwardness. Then there’s the funny bit about Brolin’s hair. Streisand was expecting someone who looked like a rugged “mountain man” and was totally thrown off by Brolin’s clean-shaven head. Her reaction was just so Streisand — she straight up asked him, “Who ‘ruined’ your hair?”
This story really highlights how their relationship is grounded in being real and comfortable with each other. Streisand being upfront and Brolin taking it in stride set the tone for a relationship that’s not about pretense, but about being genuinely themselves. “I can’t tell you how lucky I am that this would happen to me so late in life,” Brolin said in his wedding speech. “Every night is a new adventure. Sleeping is a waste of time. I can’t wait to see her again in the morning.”
Streisand, already known at the time for her distinctive and sometimes daring fashion choices, finds a solid ally in Brolin. He’s not just the guy by her side; he’s her biggest fan, no matter how unconventional her outfit might be. Whether she’s rocking a vintage look or a modern designer piece, Brolin’s support is unwavering.
Together, Streisand and Brolin defy the usual celebrity relationship narrative, showing the world that a little peculiarity, mixed with mutual support and respect for each other’s individuality, can make for an intriguing and enduring love story.
Barbra’s love story with her husband is more than just this; it even inspired a famous love song.
Preview photo credit CBS/Ferrari Press/East News, CBS/Ferrari Press/East News
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