Does Anna Wintour Wear A Wig?

Born in London in 1949, Anna Wintour wore her signature blunt bob and oversized sunglasses as early as age 14—back when she was just a fashion-obsessed teenager. Her teenage years mark the genesis of her style icons: the bob was perfect for Tory Burch-style silhouettes, and the sunglasses gave her an air of mystery.

Today we will explore:The evolution of Anna Wintour’s hairstyle—from her early days to the iconic bob (and wig rumors). Why she never takes off her sunglasses—the theories and rare sightings without them. Let’s unravel the mystery behind Anna Wintour’s enduring image.

1.The Iconic Bob Hairstyle: Does Anna Wintour Wear A Wig?

Source:DW

For nearly 50 years, Anna Wintour’s bob has stayed almost frozen in time. She first adopted it in her mid-teens and has never strayed—only fine-tuning its tone and sleekness along the way. Rumors have swirled about whether it's a wig, but those are unfounded.

She does not wear a wig. Her regular hairstylist, Andreas Anastasis, cuts, colors, blow-dries, and spray-fixes the bob at her home every morning at 8 AM. During the pandemic, he even showed up in a hazmat suit to keep her hairstyle flawless. There's no wig—just meticulously maintained natural hair.

2.Why Does Anna Wintour Always Wear Sunglasses?

Source:Forbes

Wintour is almost never photographed without her signature black shades. They’re more than a style statement—they’re strategic. In multiple interviews, she admitted that sunglasses help her conceal her thoughts, hide fatigue, and shield herself when she’s under the weather or recovering from eye surgery.

She once told CNN:“I find them incredibly useful… they help when I’m feeling a bit tired or sleepy.” In 2009 on 60 Minutes, she described them as "armor"—a tool for both psychological defense and anonymity.

A calmer 2024 BBC interview offered a more nuanced insight: “They help me see and they help me not see. They help me be seen and not be seen… They are a prop.”

Some insiders suggest that her sunglasses also house corrective lenses—she’s inherited poor eyesight from her father.

Still, she's shown the rare vulnerability—easing into conversation without shades during personal appearances, like her Damehood or at the 2023 Met Gala.

3.Rare Sightings: Anna Wintour Without Glasses

Source:Los Angeles Times

Despite her strict image, there have been a few instances where she’s been photographed without sunglasses: At Wimbledon (where she occasionally removes them in the shade). In rare interviews where she’s in softer lighting. Fans are always shocked to see her eyes—proof of how ingrained the sunglasses are in her persona.

4.Off-Duty Anna: Joggers, Casual Looks, and Unexpected Style

Source:Daily Mail

While Anna Wintour is known for her sharp tailoring and designer coats, she occasionally steps out in surprisingly relaxed outfits.

Anna Wintour in Joggers?

Yes, It Happens. Paparazzi have caught her wearing athleisure, including joggers and sneakers, while out in New York. Even in casual wear, she maintains an air of elegance—often pairing them with a chic coat or designer bag. It’s a reminder that even the most powerful figures in fashion have their off-duty moments.

5.The Trump Ban at the Met Gala

Source:Pinterest

Since becoming co-chair of the Met Gala in 1995, Wintour has steered the event toward fashion and away from overt politics. In 2017, she made headlines for one of her strictest fashion moves: banning Donald Trump from future Met Galas following his takeover of the US presidency. She’s remained resolute in these decisions ever since—maintaining that the Met Gala is a fashion event, not a political platform. 

Met Gala Appearances: Style Through the Decades

Source:Women&Home

As co-chair, Wintour isn’t just attending the Met Gala—she’s directing it. Her personal looks have consistently reflected the evening’s themes with polished reverence:

2023 – “Karl Lagerfeld: A Line of Beauty”: Chanel tribute in couture form. 

2024 – “Garden of Time”: A Loewe jacket paying homage to Charles Frederick Worth—with an all-black twist that broke her unwritten “no black” rule.

2025 – “Superfine: Tailoring Black Style”: A custom Louis Vuitton satin gown adorned with subtle floral embroidery—elegant tailoring with depth, true to her clean-yet-bold aesthetic.

Through it all, she’s remained far more invested in artistic direction and guest selection than public persona. 

6.Final Thoughts: The Iron Lady of Fashion

Anna Wintour built an image that transcends mere trend following—it's strategy, storytelling, and consistency. The bob is not a fad; it’s a personal signature. The sunglasses are not vanity; they’re privacy, protection, and purpose. 

From teenage style to Vogue’s global reign, Wintour has mastered the art of projecting power through minimalism and restraint. It’s no surprise she’s often called “the Iron Lady of fashion.” The aura she maintains is less about impenetrability, more about the clarity of her vision—fashion as language, and self-presentation as part of the message. 

7.FAQs About Anna Wintour

1.Is Anna Wintour married?

No, Anna Wintour is currently unmarried. She divorced her second husband, Shelby Bryan, after 16 years of marriage (2004–2020). Their relationship had been strained since 2013 due to financial scandals and rumors of Bryan rekindling ties with his ex-wife. Her first marriage was to psychiatrist David Shaffer (1984–1999), with whom she has two children. 

2. Where does Anna Wintour live?

She resides in New York City, primarily in a $11.4 million Greenwich Village townhouse and a Hampton estate with a tennis court and waterfront access. She is also frequently seen in London for work and events. 

3. Is Anna Wintour Jewish?

No, she is not Jewish. Born in London to Charles Wintour (a British newspaper editor) and Eleanor "Nonie" Trego Baker (an American), her family background is Anglican/Protestant.

4. Why does Anna Wintour wear the same necklace?

The signature purple amethyst necklace she often wears has royal ties: Originally owned by Queen Mary (grandmother of King Charles III), it was a wedding gift in 1893. Anna acquired it at a 1993 auction and wears it for its historical significance and as a nod to her British heritage during high-profile events.

5. How much is Anna Wintour worth?

Her estimated net worth is $50 million, primarily from her 37-year tenure at Vogue and roles as Condé Nast’s Global Editorial Director. Earlier reports of "$50 billion" were likely exaggerated.

6. Is Anna Wintour British?

Yes, she holds British citizenship (born in London, 1949) but has lived in the U.S. since the 1970s. She retains strong ties to the UK, evidenced by honors like the Dame Commander of the Order of the British Empire (DBE).

7. Who is Anna Wintour dating?

As of 2025, there are no confirmed reports of her dating anyone. After her divorce from Shelby Bryan, she has kept her personal life private.

8. Why is Anna Wintour so powerful?

Her influence stems from: Fashion Authority: Leading Vogue since 1988, shaping trends and launching designers like Marc Jacobs. Cultural Impact: The Met Gala’s transformation into a global event under her direction. Political Connections: Fundraising for Obama and Clinton, with rumored ambassadorial prospects. Media Portrayal: The Devil Wears Prada cemented her reputation as a formidable icon.