The Unbelievable Story of Stephanie Winston Wolkoff and the White House
Stephanie Winston Wolkoff, whose career in the fashion industry had her mingling with high society, found herself in the unexpected role of advising First Lady Melania Trump. Despite her experience and connections, the tumultuous environment of the Trump White House shifted her journey in ways she hadn’t anticipated.

Shortly after the inauguration of President Trump in January 2017, Melania Trump introduced Stephanie Wolkoff as an advisor. This appointment was significant because it happened before filling other key roles like chief of staff or social secretary.

The media buzzed with stories about Wolkoff joining Melania’s team, speculating on how the reserved First Lady might evolve in her new position. Many saw Wolkoff as a crucial player in shaping Melania’s public image.

With both women in their late forties, Wolkoff quickly became a central figure in the East Wing, handling media relations, planning events, and differentiating Melania from the President’s boisterous persona.

Wolkoff had once remarked on Melania’s virtue of silence and quiet confidence during the 2016 campaign, advising not to underestimate the First Lady merely because she was less vocal or visible.

Known as a longtime friend of Melania Trump, Wolkoff also played a pivotal role in organizing Donald Trump’s inauguration, overseeing many key aspects. However, her company’s hefty earnings from the event eventually led to controversy.

The New York Times reported that her firm received substantial payments from the inaugural committee, sparking backlash since the event was less grand than previous inaugurations despite raising twice as much money.

Wolkoff stated that the earnings were divided among her team but could not avoid the fallout. Following the controversy, Melania’s office announced it was ending their professional relationship.

Back in 2000, Wolkoff had what seemed like the perfect life, marrying David Wolkoff, a real estate tycoon. At Vogue, where she spent 11 years, her work greatly influenced the fashion industry’s social events.

Wolkoff and Melania’s friendship flourished over the years, often being seen together at significant events, which included the fashion world’s elite gatherings.

Even when Wolkoff left Vogue for Lincoln Center in 2009, the friendship endured. However, without Vogue’s support, her influence in the fashion industry began to wane, highlighting the reliance on her previous associations.

Despite challenges, Wolkoff was known for her generous spirit, often backing charitable causes. However, as she veered away from her established circles, her attention largely turned to her friendship with Melania.

Many friends cautioned her against aligning with the Trumps, fearing reputational damage. Yet, Wolkoff saw potential in leveraging her role with Melania to revitalize her ties to the fashion elite.

While Melania’s team noted Wolkoff’s past prominence as beneficial during the turbulent transition to the White House, the partnership didn’t last. The fallout brought her back to a world where former Trump associates find themselves overlooked once their usefulness ends.

These events serve as a reminder of the unpredictable and often unforgiving dynamic surrounding the Trump family.