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Meet the Woman Aiming to Surpass Anna Wintour from Small-town Oregon
- TheSwishCompany
- Jul 2
- 6 min read
By all modern accounts, Taylor Bennett shouldn't be the one redefining women's media. She doesn't operate from a major city. She doesn't follow trend cycles. She isn't mimicking celebrity culture. But from her small town life, she is setting a new standard, one that is marked by intentional glamour, quiet confidence, and a belief that elegance is a decision available to any woman who wants it.
Her magazine, Vesper, launched this year without a corporate strategy but instead a deep conviction that women are looking for something different. Her conviction that femininity is not outdated but waiting to be reclaimed, inspires women worldwide to see that real elegance is not restricted by geography, social status, or cultural fashion. Rather, Taylor shows her growing audience that elegance is formed through habit, family, memory, and a little bit of star power.
Taylor’s Roots
Taylor Bennett's definition of elegance did not come from social media, film, or fashion school. It came from her grandmother. Raised in Hollywood, her grandmother once lived among marble floors, cocktail parties, and designer gowns. But when the family was robbed and the city began to shift, they moved to rural Oregon and a life with dirt driveways and livestock.
Rather than mourn her past, Taylor’s grandmother adapted. Yes, she became a ranch wife, but she still hosted elegant dinners with music, candlelight, fresh food, and warmth. Her manner, voice, and posture remained dignified. What changed was not her character, but only her environment. Taylor grew up watching her grandmother bring beauty into even the most rustic of places.
That influence continued through Taylor’s mother, who, despite her more tomboyish lifestyle, saw the spark of femininity in her daughter. Taylor was encouraged to play dress-up, to parade in tiny gloves and sequin-covered dresses and to delight in being a “lovely lady”, as her mother called her. The Vesper editor-in-chief recalls a childhood full of fashion shows in her living room and homemade illustrations of glamorous women. It was never about being rich or famous but about carrying herself with dignity, grace, and strong imagination.
Audrey and Taylor, The Start of It All
At age eighteen, Taylor experienced a moment that would unexpectedly shape her future. While traveling in Europe, she was mistaken by a stranger for Audrey Hepburn.
At first, the comparison was humorous, but it sent Taylor on a deeper journey to understand who Audrey really was. She read biographies, watched films and found not just aesthetic inspiration, but a model of strength and integrity lost in modern celebrity culture.
Audrey had survived hardship and loss during the war. She pursued beauty with restraint and lived with compassion.
Her life was not perfect, but it was consistent with her values. The golden-age icon spoke softly, lived intentionally, and valued simplicity. This balance of grace and grit became a blueprint for Taylor’s own understanding of what femininity could look like.
A Need for New Media
Vesper began unintentionally. While Taylor had written fiction, published a nonfiction book, and was preparing to return to fiction, her publishers kept asking her to build a bigger platform. To do so, she began writing articles for other women’s publications and at first, it worked. Her pieces performed well, but the deeper she went, the more disillusioned she became.
She noticed that even the more traditional publications were beginning to glamorize styles of femininity she didn’t agree with. They celebrated overt sensuality, superficial charm, and trashy celebrity culture, that was even dressed up in conservative language. When Taylor tried to pitch a piece critiquing pop singer Sabrina Carpenter’s brand of suggestive femininity, she was told the magazine would not run it. That moment confirmed what had been building for months. She no longer wanted to place her voice in outlets that diluted or contradicted her convictions.
She wanted to create a space that would represent a different kind of woman.
Taylor wanted to build a place for the woman who believes beauty and virtue belong together. A woman who dresses with care, not to attract attention but to honor herself and others. A woman who does not see herself as less valuable because she is not famous, wealthy, or widely followed. A woman who sees the act of living well as a kind of quiet protest against chaos, noise, and moral confusion. The same type of woman, might we add, that reads The Swish!
Vesper was born in a matter of days. First an idea, then a name, and then an Instagram account. Taylor told herself if she reached one hundred followers she would buy the domain. She reached it in three days. Then, the website followed and subscribers signed up and within two months, Vesper had momentum.
One of the strongest convictions behind Vesper is that femininity is not a partisan issue. It is not a matter of political allegiance. It is older than voting blocs and talking points. Taylor believes modern media often pushes women to adopt either hyper-politicized personas or consumerist identities. The result is a divided and, frankly, disoriented landscape.
Vesper is different. Its editorial voice is rooted in tradition without being preachy and its vision is aspirational without being unrealistic. And its goal is not to build a cult of personality, but to remind women they already have what they need to live with elegance, dignity, and grace– no need to give in to the latest influencer trends and hauls.
Taylor is not interested in adding noise to the current cultural conversation, but rather she offers clarity to women worldwide with frameworks and analyses that are actually helpful. Rather than spending time debating the latest political issue, she prefers to provide tools, stories, and recommendations that help women take ownership of their daily choices-- from how they dress to how they host a meal, with every detail mattering.
Taylor’s most important message is that glamour is not about spectacle, but about attention; attention to detail, to values and to the life you are already living, reminding her audience what being a "main character" is all about.
This is why her morning walks matter so much, she tells me. Every day, she gets outside, regardless of weather, and reconnects with the natural world. She believes that when women observe nature, they begin to see their own beauty more clearly, not as something curated or airbrushed, but as something authentic and dignified. She doesn’t walk to exercise but to think, to listen, and to be reminded that beauty is in the details.
What’s Next for Vesper?
Vesper will release its first official issue on September 2nd, followed by a quarterly publishing schedule. While the publication is still new, Taylor has already begun interviews and features with women she’s long admired. Despite building this rising empire, Taylor is also pursuing her MBA– not for the title, but to learn how to grow the magazine with excellent acumen.
She no longer sees herself as just a writer, but building something much bigger that might reshape how women see themselves in the years ahead.
After Anna Wintour announced in June that she is stepping down after more than thirty years at the helm of the famous and influential Vogue, Taylor shared a bold personal and professional goal with her audience: she wants to surpass Anna Wintour. Not in aesthetic shock value, celebrity status, or runway dominance, but in cultural impact. She wants to help redefine and reframe what women’s media can look like for the next generation.
In a time when so much women’s media relies on shock value, there is a choice to speak with gentleness and conviction. Through Vesper, Taylor is offering a countercultural platform built not on angry rebellion, but the quiet truth. She is inviting women to remember the strength of softness, the power of tradition, and the joy of living a life that is lovely not because it’s big, but because it’s intentional.
If the future of women’s media looks more like Vesper and less like celebrity tabloids, it will not be because of a marketing campaign. It will be because women like us at The Swish supported a network of outlets celebrating true and rooted femininity. We have growing alternatives to mainstream media narratives, all because women like Taylor and outlets like Vesper, believed it was possible.
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