The Devil Wears Prada vs Working Girl: Two Generations of Women Climbing the Ladder

 

When The Devil Wears Prada premiered in 2006, audiences immediately recognised its glossy depiction of ambition and sacrifice. It was witty, infinitely quotable, and unapologetically stylish—a film that turned fashion into both armour and prison. But beneath its couture surface lay a story as old as work itself: a young woman trying to make it in a world built by and for the powerful, wondering if the cost of entry might be her soul.

Nearly two decades earlier, Working Girl (1988) told a remarkably similar tale. Tess McGill, the Staten Island secretary with a business degree, big dreams, and an even bigger accent, also fought to be taken seriously in a corporate world ruled by men—and occasionally by women who had learned to play by their rules. Her weapon wasn’t a designer wardrobe but sheer determination wrapped in shoulder pads the size of Delaware.

Viewed together, these films offer a fascinating masterclass in how stories of female ambition have evolved. They speak to radically different ideas about work, class, and the price of success, while revealing how certain compromises—the ones we make with ourselves—never quite go out of style. One film ends with a woman claiming her rightful place in the system. The other ends with a woman walking away from it entirely.

Let’s talk about why both endings matter.

Two Entrances, Same Revolving Door

Both Andy Sachs (The Devil Wears Prada) and Tess McGill (Working Girl) begin their journeys at the bottom floor of power, noses pressed against the glass ceiling. Andy, a fresh Northwestern graduate with journalistic dreams and sensible shoes, stumbles into the fashion magazine Runway and becomes assistant to Miranda Priestly, the terrifyingly composed editor-in-chief who can destroy careers with a whisper. Tess, meanwhile, works as a secretary in the testosterone-soaked world of Wall Street mergers, her intelligence constantly underestimated because of her working-class background and outer-borough accent.

Each woman’s entrance scene tells us everything we need to know. Andy, awkward in her clashing sweater and boots, walks through the polished glass doors of Runway while sleek assistants watch with the disdain usually reserved for tourists wearing fanny packs in Milan. Tess, in her teased hair and boxy suit with linebacker shoulders, rides the Staten Island Ferry while Carly Simon’s “Let the River Run” swells triumphantly and her voiceover plays snippets of motivational radio. Both are dreamers perched on the edge of reinvention, about to discover what transformation actually costs.

But here’s where they diverge. Working Girl makes class its central battlefield—Tess’s “head for business and bod for sin” (her words, not ours) versus the elite polish of her boss Katharine Parker. The Devil Wears Prada shifts the focus to culture and identity. Andy isn’t from another social class exactly, but from another planet entirely. She values intellect over appearance, principle over prestige, The New Yorker over Vogue. Her clash with Miranda isn’t about money or education—it’s philosophical warfare. What kind of work deserves your life? And when does dedication become self-destruction?

The Bosses: Elegant Predators in Designer Armour

If Tess and Andy are our entry points, their bosses define the battlefield’s bloodiest terrain. Sigourney Weaver’s Katharine Parker and Meryl Streep’s Miranda Priestly are two of cinema’s most unforgettable women in power—elegant, poised, and ruthless in utterly different ways that reveal how power rewrites personality.

Katharine in Working Girl is the archetype of the “fake mentor,” the woman who learned all the right progressive language but none of the ethics. She presents herself as a champion of other women, warmly encouraging Tess’s ideas while quietly stealing them like a corporate pickpocket. When she takes credit for Tess’s brilliant merger pitch, it’s not just betrayal—it’s a damning commentary on how women in male-dominated spaces sometimes adopt the worst masculine behaviours to survive. She’s proof that feminism without solidarity is just careerism in lipstick.

Miranda, in contrast, is no impostor. She is power incarnate, distilled into a white bob and impeccable posture. Her cruelty is refined, her authority absolute, her whisper more terrifying than anyone else’s scream. She doesn’t pretend to be anyone’s friend or mentor. Streep plays her not as a villain but as a tragic monument to control—someone who sacrificed warmth, vulnerability, and perhaps her entire humanity to maintain her throne in an industry that would happily replace her with someone younger, prettier, more grateful.

Unlike Katharine, Miranda doesn’t steal ideas; she appropriates entire lives. She doesn’t need to take credit because everyone already knows: nothing happens at Runway without her blessing. Her power is so complete it’s become her prison.

Both characters reveal how power distorts female identity in patriarchal systems that reward aggression but punish women for displaying it. Katharine weaponizes charm and social grace, playing the game with a smile. Miranda weaponizes silence and ice, ruling through fear so refined it looks like elegance. One seeks validation; the other demands worship. Yet both are, in their own way, punished by the world they mastered. Katharine loses everything when Tess exposes her deceit in a glorious boardroom showdown. Miranda loses something quieter but deeper: intimacy, authenticity, the ability to be vulnerable without it being weaponized against her.

Fashion as Language, Costume as Armour

Clothes are not just decoration in these films—they’re the primary language, the grammar of power. In Working Girl, fashion is pure aspiration, the 1980s fantasy that women could literally “dress for the job they want” and somehow conjure it into existence. Tess’s shoulder pads, teased hair, and pastel suits symbolize an era that believed transformation was mostly a matter of will and the right wardrobe. When she cuts her hair, changes into Katharine’s stolen clothes, and borrows her boss’s office to pitch her merger idea, she’s performing a version of herself that corporate America will actually listen to. Her transformation is literal and social: the right outfit grants access to the room where decisions get made.

By 2006, The Devil Wears Prada takes that same trope and turns it deliciously inside out. Fashion isn’t a disguise that helps you succeed; it’s a test of loyalty, a uniform that marks how deeply you’ve surrendered. Andy’s makeover—her Chanel boots, tailored coats, and glossy blowouts—is her golden ticket into Miranda’s inner circle, but also the beginning of her moral drift. The more beautiful she looks, the further she strays from her sense of self. She becomes the thing she once dismissed, and the film makes us complicit in admiring her transformation.

In one of the film’s most brilliant scenes, Nigel explains fashion’s hidden power to Andy after she dismisses it as trivial: “You think this has nothing to do with you.” He traces her “lumpy blue sweater” back through department stores, designers, and ultimately to a cerulean-blue runway collection from years prior, reminding her that even rebellion is part of the system. It’s a speech that exposes the invisible web of power behind every choice we think is personal, sartorial or otherwise. Nothing is neutral. Everything is political.

Where Tess uses fashion to rise—costume as rocket fuel—Andy uses it to disappear into someone else’s vision. And she must eventually undress her ambition completely to find herself again.

Love, Sacrifice, and the Impossible Balancing Act

Romance, in both films, serves as mirror and measure of what success actually costs. Tess’s relationship with Jack Trainer is presented as the ultimate reward for persistence: she wins both the deal and the man. He respects her mind, supports her ambitions, and helps her navigate a system designed to chew her up. Their partnership feels like a hopeful late 80s dream that personal and professional success could coexist without one consuming the other.

Andy’s relationship with Nate offers a more complicated, modern realism. He loves her, or at least he loves the version of her that had time for his birthday and didn’t cancel dinner seventeen times. Their breakup feels inevitable, not tragic—the natural result of incompatible priorities. When he accuses her of becoming what she despised, he’s not entirely wrong, but he’s also not entirely innocent. His resentment reeks of male entitlement to female attention.

By the time Andy throws her phone into a Parisian fountain—one of cinema’s most satisfying symbolic gestures—she’s not choosing Nate over work. She’s choosing herself over the machine that nearly ground her into something unrecognizable. The film understands that sometimes the bravest thing a woman can do isn’t lean in—it’s walk away.

This evolution in storytelling reflects broader cultural shifts. Working Girl was born in an era of Reagan-era optimism, when “having it all” still sounded achievable if you just worked hard enough and wanted it badly enough. The Devil Wears Prada, made in the shadow of burnout culture, global capitalism, and the realization that meritocracy was always partly mythology, knows better. It understands that ambition in toxic systems often demands a kind of self-erasure—and that walking away can be the most powerful move on the board.

The City as Character: Promise vs. Predator

Both films treat New York as far more than a backdrop—it’s practically a third protagonist. In Working Girl, the skyline glows with possibility. The ferry rides, crowded subways, and soaring skyline montages are infused with Capra-esque hope. The city may be tough, competitive, exhausting, but it rewards the brave and the brilliant. The score swells; the camera lingers lovingly on Tess’s smile as she looks out over Manhattan. It’s a hymn to upward mobility, American Dream propaganda shot through with genuine affection.

By contrast, The Devil Wears Prada presents New York as an elegantly designed pressure cooker. The city’s lights glare rather than shine. Its offices are cold temples of minimalism, its cafés sterile, its apartments shrinking by the minute despite astronomical rents. Andy’s story unfolds against a relentless background of deadlines and red lights, where glamour is just exhaustion in better lighting. Even Paris—Paris!—becomes another workplace, another test, another opportunity to lose yourself in someone else’s vision.

In short, Working Girl makes New York a dream to conquer through determination and moxie. The Devil Wears Prada makes it a system to survive through compromise and calculation. Same city, radically different mythology.

Feminism: Then and Now, Here and There

The feminist subtext in Working Girl is wonderfully explicit, almost didactic. Tess is fighting visible, nameable sexism in a man’s world—sexual harassment, intellectual theft, class prejudice. Her triumph—claiming her idea, her job, and her corner office with a view—is presented as a victory for working women everywhere. The film’s final shot, pulling slowly back from her new window desk overlooking Manhattan, celebrates her success as both personal achievement and collective progress. She has risen. Roll credits on hope.

The Devil Wears Prada is trickier, more ambivalent, more interested in uncomfortable questions than satisfying answers. It’s less about breaking glass ceilings than questioning what’s actually on the other side of all that broken glass. Andy already has access to a prestigious workplace. Her challenge is moral and existential, not institutional. She must decide whether success defined by others is worth the loss of her integrity, relationships, and sense of self. The feminist question here isn’t “Can women succeed in male spaces?” but rather “What does success even mean in systems designed to extract everything from us?”

In this way, Prada feels distinctly contemporary. It recognizes the hollow center of achievement in a capitalist society that measures worth by productivity, visibility, and image. It also resists easy labels or simple heroines. Miranda is simultaneously monster and role model, victim and perpetrator. Andy is both exploited assistant and willing accomplice. No one escapes cleanly, and that moral complexity is precisely the point.

Men in the Margins (Where They Belong)

It’s striking how secondary men are in both films—a refreshing reversal of cinematic norms. In Working Girl, they represent the old order: crude bosses who hit on secretaries, clueless colleagues who can’t imagine women having ideas, or, in Jack’s case, a decent man awkwardly learning to share professional space with a woman’s ambition. They’re obstacles, allies, or romantic rewards, but rarely the main event.

In The Devil Wears Prada, men orbit the female sphere like decorative satellites. Nate, Nigel, and Christian all serve primarily as reflections of Andy’s evolving choices. They don’t drive the story; they expose its stakes through their reactions. This female-centric framing is part of what makes both films enduring. They acknowledge that women’s professional journeys often unfold in relation to other women—mentors, rivals, allies, cautionary figures—far more than to men. The real relationships are between women who understand the game’s actual rules.

The Mirror Effect: Reflection as Revelation

Both stories end with mirrors—literal or symbolic—because that’s where identity lives. Tess sits in her new office with its wall of windows, looking out at the world she’s earned through intelligence and guts. Her reflection in that glass confirms she belongs, that she’s arrived, that the system can accommodate her if she fights hard enough.

Andy catches her reflection in a shop window after her final encounter with Miranda, smiling at her former boss’s subtle nod of approval before walking confidently away. Her reflection reminds her that belonging isn’t everything, that approval from the wrong people is its own trap. She’s choosing uncertainty over security, self-definition over external validation.

Together, these mirror moments chart a cultural arc from arrival to awareness, from breaking in to breaking free. The first film believes passionately in transformation through assimilation—become what they need, claim your seat. The second believes in transformation through rejection—recognize the trap, walk away with your humanity intact.

Why They Still Electrify Us

Despite being products of radically different eras—one born of 80s optimism, one of millennial disillusionment—Working Girl and The Devil Wears Prada remain in vital conversation because they speak to ongoing tensions in women’s lives: ambition versus authenticity, independence versus belonging, empathy versus control, success versus sanity.

Tess McGill kicked open the door for women to imagine themselves in power, to believe that intelligence and determination could overcome class barriers. Andy Sachs walked through that opened door—and then asked whether the room on the other side was worth staying in, whether the view justified the claustrophobia.

Both films also endure because they’re supremely, unapologetically watchable. Melanie Griffith’s warm resilience, Harrison Ford’s easy charm, Sigourney Weaver’s controlled menace, Streep’s volcanic restraint, Anne Hathaway’s expressive vulnerability, and Stanley Tucci’s scene-stealing wisdom all make their respective journeys believable and compelling. Each film reflects the aesthetics of its decade—Working Girl’s neon confidence and power ballads, Prada’s minimalist polish and cutting wit—while exposing the anxieties pulsing underneath the surface.

From Shoulder Pads to Smartphones: What Has Changed (And What Hasn’t)

If Working Girl were remade today, Tess might be a tech startup founder pitching venture capitalists instead of proposing corporate mergers. If Prada premiered now, Andy’s world would unfold on Slack and Instagram, where ambition is measured in followers and personal brands, where you’re never truly off the clock because your phone is your office.

But strip away the technology and aesthetics, and the emotional core remains devastatingly the same. Women still navigate systems that reward appearance, emotional labour, and strategic silence differently than they do competence. The wardrobe has evolved from shoulder pads to athleisure, but the fundamental rules of the game—who gets heard, who gets promoted, who gets believed—haven’t changed nearly as much as we’d like to think.

Conclusion: The View from the Top (And the Exit)

In the end, The Devil Wears Prada and Working Girl aren’t opposites but consecutive chapters in the same long, complicated story about women, work, and the perpetually moving goalposts of success. Tess fought brilliantly to enter the building, to claim her chair at the table. Andy learned intimately how much the climb can cost once you’re inside, how success can hollow you out if you’re not vigilant about protecting what makes you you.

Both films ask the same essential question in different keys: what does it take for a woman to be seen, heard, valued—and at what price?

Perhaps the answer lies somewhere between their endings—between Tess’s triumphant smile in her corner office and Andy’s quiet exit from the system entirely. Success, after all, isn’t always about getting the corner office with the killer view. Sometimes, it’s about having the courage to decide which tower you’d rather not climb, which view isn’t worth the vertigo.

Both women win, in their own ways. Both women also lose something in the victory. And that tension—between what we gain and what we sacrifice, between who we become and who we leave behind—is why these films still speak to us across decades and shifting cultural landscapes.

Because the question isn’t really whether women can succeed in systems designed without them in mind. We know they can. The question is whether those systems deserve their brilliance at all.