Devil Wears Prada Realness: Anna Wintour’s Former Assistants Share the Ultimate Fashion Career Blueprint

If you’ve watched The Devil Wears Prada more times than you’ve had hot dinners (guilty!), you’ve definitely wondered: what is it actually like to be the right hand of the nuclear Wintour herself? Is it all flying across the globe in a private jet and throwing coats on desks, or is it more about survival, grit, and very high-end coffee runs?

With the massive hype surrounding the release of The Devil Wears Prada 2, the timing couldn’t be more perfect. Two of Anna Wintour’s real-life former assistants—Sammi Tapper (now Director of Operations at Vogue) and Marley Marius (Senior Editor at Vogue)—recently sat down to spill the tea. They’ve traded their “assistant” titles for major masthead roles, and they’re sharing the kind of career advice you won’t find in a textbook.

At D-Muse Magz, we’re obsessed with the “Office Core” aesthetic and the high-stakes world of fashion media. Whether you’re dreaming of the front row at Paris Fashion Week or just trying to navigate your first internship, here is the wisdom from the women who survived—and thrived—under the most famous bob in fashion.

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1. Mistakes Aren’t the End of the World (Promise!)

When you’re working for someone like Anna Wintour, a typo or a misplaced handbag can feel like a national emergency. Sammi Tapper’s biggest tip? Learn to separate yourself from the moment.

“You will likely make a handful of trivial mistakes. Sometimes, you can be made to feel like they are the end of the world,” Sammi explains. She suggests asking yourself: “Is this going to matter in a week? Is it going to matter in two months?” If the answer is no, move on. In 2026, where digital news moves at the speed of light—much like the flurry around Sabrina Carpenter’s missing Madonna costumes—dwelling on a small slip-up is just wasted energy.

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2. Find Your “Cabal” of Peers

Fashion can be an isolating industry, especially when you’re at the entry level. Marley Marius credits her survival to the two other assistants in the office. Even if they weren’t best friends, they were a team that trusted each other.

Having people who “get it” makes the long hours and high-pressure meetings at Coachella 2026 or the Cannes Film Festival bearable. If you like your team, your quality of life skyrockets. It’s the “parasocial” bond turned into a real-life support system.

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3. Lean Into the Scars (and the Scary Meetings)

Marley admits that she is constantly presented with tasks where her first thought is, “I cannot do this.” But after surviving the “bootcamp” that is Anna Wintour’s office, she realized that most things won’t actually kill you.

Whether it’s walking up to an intimidating celebrity like Anya Taylor-Joy for an interview or presenting in a high-stakes meeting with Jonathan Anderson, the only way to build the skill set is to do it. As Sammi puts it: “You’re not supposed to have all the answers when you start.” Be gentle with yourself—everyone was a 22-year-old beginner once.

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4. Ask the “Smart” Questions

There’s a huge temptation in fashion to “fake it ’til you make it.” Don’t. Marley learned the hard way that risking a moment of embarrassment by asking a question is way better than causing a massive mistake later because you pretended to know what was going on.

“I quickly learned that you just need to risk embarrassing yourself to avoid embarrassing yourself even more,” Marley says. People are usually happy to help because it saves them work later on. Even Anna Wintour knows you’re young—she’s had dozens of assistants; you aren’t the first one to be confused by a seating chart!

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5. Persistence Over “Bylines”

If you want to be a writer or a stylist, don’t wait for a fancy magazine to give you permission. Marley’s advice for the 2026 creator is simple: just start. Make a Substack, submit to small zines, or create your own digital “muse” media.

Luck and privilege (knowing the right people) definitely play a part in the industry, but there is no substitute for building your skill set on your own time. Much like No Na worked their way up through 88rising, you have to hone your craft before you hit the big stage.

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6. Plant Your Seeds (The LinkedIn Strategy)

Sammi Tapper uses a beautiful metaphor: plant as many seeds as you can. Today’s LinkedIn message or coffee date might not pay off for seven years, but eventually, things come full circle.

She reached out to people as a sophomore in college for 15-minute Zoom calls, and years later, those people became her colleagues. It’s about patience. You never know when a seed you planted during your “Bieberchella” era will sprout into a major career opportunity.

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7. Don’t Compare Your Timeline

In a world where we see Blue Ivy Carter or Rosé achieving global icon status at a young age, it’s easy to feel like you’re behind. But Sammi and Marley are proof that the assistant life is just a stepping stone. Your timeline is yours alone. Whether you’re a “Sad Prince” like in Perfect Crown or a rising star, your path is unique.

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The D-Muse Final Verdict

Working for Anna Wintour isn’t just about the prestige; it’s a masterclass in resilience. The advice from Sammi and Marley boils down to one thing: be kinder to yourself. You’re allowed to be scared, you’re allowed to ask questions, and you’re definitely allowed to make mistakes.

As we move into the summer of 2026, take these lessons with you. Whether you’re heading to the American Music Awards red carpet or just starting your first day at a local boutique, remember that even the most powerful women in fashion started exactly where you are.

Which piece of ‘Devil Wears Prada’ advice resonates most with you? Are you a chronic procrastinator when you’re scared, or are you ready to start “planting seeds” on LinkedIn? Let us know in the comments—and tell us, who is your ultimate “Boss Muse” in the fashion world!

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