How Much Is Anna Wintour’s Social Security Check?
Written by
Laura Beck
Edited by
Molly Sullivan
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After 37 years as editor-in-chief of Vogue, Anna Wintour just announced she’s stepping down from the role. While everyone’s talking about who’ll replace the fashion icon who inspired “The Devil Wears Prada,” we got curious about something totally different: What’s her Social Security check look like?
Here’s the thing that might surprise you: At 75, Wintour is probably getting one of the biggest Social Security checks the government sends out each month. (And yes, even fashion icons have to deal with Social Security just like everyone else.)
Here’s how much Anna Wintour’s Social Security check is each month.
Social Security 101
If you work in America and pay taxes, you’re paying into Social Security whether you’re flipping burgers or running Vogue. Even if you’re worth an estimated $50 million like Wintour, you still get those Social Security taxes taken out of your paycheck.
The catch? Social Security wasn’t designed to make rich people richer. It was created to keep older Americans from living in poverty. But if you’ve been paying in for decades, you’re entitled to get something back.
Why Being 75 Actually Helps Her
Most people think you retire at 65, but Social Security is way more complicated than that. You can start collecting at 62 if you want, but your monthly check will be smaller than if you waited.
For someone born in 1949 like Wintour, “full retirement age” was 66. That means if she waited until 66, she’d get 100% of whatever the government calculated she deserved. But if she was really smart (and let’s be honest, she probably was), she waited until 70 to start collecting. Why? Because for every year you wait past your full retirement age, your monthly check gets bigger — up to 32% bigger.
Since Wintour kept working at Vogue way past when most people retire, she probably waited until 70 to start collecting Social Security. That decision alone could have made her monthly check over $1,000 bigger.
The Math Behind the Money
Here’s where it gets interesting. Social Security looks at your highest-earning 35 years, adjusts them for inflation, and then uses a formula to figure out your monthly payment. The formula is designed so that people who didn’t make much money get a higher percentage of their income replaced, while high earners get a smaller percentage but still a decent amount.
But there’s a cap. In 2025, you only pay Social Security taxes on the first $176,100 you earn each year. Anything above that? No Social Security taxes. This means whether you make $200,000 or $4 million (like Wintour reportedly did), you’re only paying Social Security taxes on that first $176,100.
This might seem unfair, but it also means there’s a limit to how much you can get back. The maximum Social Security check in 2025 is $5,108 per month if you waited until 70 to start collecting.
What Wintour Probably Gets
Given that Wintour has been making serious money in fashion, she almost certainly qualifies for that maximum benefit. Her estimated monthly Social Security check? Around $5,100.
That might sound like a lot but think about it this way: That’s about $61,000 per year. For someone who was making $4 million annually at Vogue, that Social Security check represents about 1.5% of her former salary. It’s nice to have, but it’s not exactly life-changing money for someone with her wealth.
Putting It in Perspective
To put this in perspective, Wintour’s Social Security check is probably less than what she spends on her monthly electric bill for her $11.5 million townhouse in Greenwich Village. She also owns a massive estate in Long Island worth somewhere between $10 million and $15 million. Her Social Security is basically pocket change compared to her overall wealth.
That said, she gets the exact same maximum amount as a construction worker or teacher who also maxed out their Social Security contributions for 35 years and waited until 70 to retire. The government doesn’t care that she’s Anna Wintour; the formula is the same for everyone.
Why This Matters
This whole situation shows something interesting about how America handles retirement. Even the most successful people participate in the same Social Security system as everyone else. The difference is that for most people, Social Security replaces a much bigger chunk of their working income. For the average retiree, Social Security might replace 40% of their pre-retirement income. For Wintour, it’s more like 1.5%.
The system is designed to provide a safety net for everyone, but it’s not supposed to maintain your exact lifestyle if you were already super wealthy.
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