The 3 Best Dressed & 3 Worst Dressed Nepo Babies In Hollywood

Once upon a time in Hollywood, it was just possible enough to ascend with raw talent and audacity (and maybe a little luck). That version of the industry hasn't vanished entirely, but these days, the odds aren't quite so democratic. In 2025, the path into showbiz tends to be smoother if you emerge from the right gene pool. Nepotism is hardly new, but it's never been more concentrated and conspicuous. For those without a famous surname to break through, the climb is more brutally difficult than ever.

What remains stubbornly immune to inheritance, however, is style. You can be born with your father's jawline and have your mother's fashion house on speed dial, but lineage is no guarantee of taste, which is proving harder to outsource. It takes more than nepo babies just wearing their celeb mom's iconic dresses to stake a claim to fashion legitimacy. And while some second-gen heirs to the spotlight lean in with a sharpened sense of style identity, others appear trapped in a revolving door of loaned looks and ill-advised experimentation.

Hailey Bieber's infamous "nepo baby" t-shirt attempted to reclaim the term as a wry fashion statement in itself. But irony only gets you so far on the red carpet. For every well-dressed progeny, there's another whose style rarely rises above the realm of well-funded misjudgement. So, who is carrying the family torch, and who's singed it beyond repair?

Kaia Gerber may have inherited one of the most symmetrical faces in modeling history, courtesy of Cindy Crawford, but her style is no carbon copy. Among the current nepo baby crop, she's one of the few whose fashion sense feels consciously developed with real taste. She gravitates towards soft, retro-inflected tailoring, ballet flats, and ingénue dresses, contributing to looks that suggest an Upper West Side intellectual raised on Joan Didion, just relocated to Silver Lake.

She's frequently ahead of the fashion curve, as evidenced by her take on the party dress from the early aughts staging a 2025 comeback. She certainly knows how to make nostalgia feel directional. But her sartorial savvy extends well beyond red carpets. The baby tees sold for Kaia Gerber's book club are routinely ever so popular, proving she knows what Gen Z wants to wear. Overall, she dresses like someone who grew up backstage, but never lost the cool curiosity of the girl watching from the wings.

Brooklyn Beckham, son of footballer David Beckham and Spice Girl Victoria, is perhaps the nepo baby most visibly in identity crisis. His style, much like his résumé, suggests a man desperately trying things on to see what might fit. First came the photography book, panned for its blurry compositions and mystifying captions. Then a foray into cooking, which mostly involved plating pre-cooked meat and squirting ketchup on a sandwich like it was a culinary breakthrough. In one cringe-inducing photo, he posed moodily over a saucepan — having accidentally dropped a wine cork into it, thinking we wouldn't notice.

But fashion might be his most telling misstep. Brooklyn's default uniform is backwards baseball cap, scruffy tee, and trousers. But when Vogue profiled him and wife Nicola (with the weirdest parts of their marriage being hard to ignore), commenters were quick to point out the obvious. "He has no business looking like this as David Beckham's son," wrote one. Another simply observed, "He looks like the guy who comes to fix your boiler."

He often dresses to match with Nicola, which might be classed as romantic if it didn't so often land them both on worst-dressed lists. It only reinforces the notion that he's still figuring out who he really is, stylistically and otherwise. If he had a clearer sense of self, maybe his wardrobe would reflect it. And with access to his parents' bank account, there's really no excuse.

Bill and Melinda Gates' daughter Phoebe is so stylish, she's turned her wardrobe into a business model. In 2025, she co-launched Phia, a fashion-tech app developed with her former Stanford roommate and designed to do for secondhand shopping what Bloomberg Terminals did for Wall Street. It uses AI to track market trends and compare prices of designer labels across millions of listings, promising you the best cost for your couture.

As both a tech heiress and a tech founder in her own right, she's certainly dressing for the part. Her Instagram offers a wardrobe that pulls references from the boardroom: clean limes, minimalist jewelry, flattering knitwear, and sharp ponytails (yes, she's nailed the office siren aesthetic). But there's also a clear Gen Z sensibility at work — a playfulness in proportion, unexpected color pairings, and contrast. On the red carpet, she shows a strong appreciation for couture eveningwear, with the occasional high-drama moment.

These days, Blake Lively tends to keep her nepo baby credentials tucked discreetly behind the curtain, but let's not pretend the path wasn't pre-saved. In fact, it's the kind of leg-up you'd expect to see on "Gossip Girl." She's the daughter of actor-director Ernie Lively, who happened to play her onscreen father in her breakout role in "The Sisterhood of the Traveling Pants," back in 2005. She made her actual debut even earlier, in "Sandman," a film directed by her dad. Her mother, Elaine, worked as both a talent agent and actor, and her older brother's agent reportedly helped her land those all-important early auditions.

Still, whilst her Hollywood entry may have been smoothed by family ties, her fashion choices have taken a bumpier route. For better or (usually) worse, she dresses herself, but there is an abundance of outfits that prove Lively needs a legit stylist. Her 2025 appearances have landed among the worst-dressed celebrity street style outfits of the year. As one Reddit user surmised, "I've literally never seen anyone in my life–especially not anyone with money–have such a bafflingly awful sense of 'style.' It's brutal."

Romy Mars is a relative newcomer to the nepo baby circuit, but she made quite the entrance. Born in 2006 to director Sofia Coppola and Phoenix frontman Thomas Mars, she was largely raised out of the public eye — until a TikTok in 2023 catapulted her straight into the spotlight. In the video (quickly deleted), Romy casually confessed she's been grounded for attempting to charter a helicopter using her dad's credit card to go have dinner with a camp friend. It was so outrageous, so unbothered, so perfectly nepo-core, that it became instantly iconic. A teen too rich to function — but charmingly self-aware.

Her style runs on that same low-key, dreamy frequency. She relies heavily on girl-next-door basics, often looking like she's wandered out of a modern-day "Virgin Suicides" wardrobe department (it's in her DNA, after all). She mixes textures and keeps her silhouettes easy, channeling a Tumblr blog from 2016 in the best way.

Nepo babies become their most insufferable when they try to argue the term shouldn't apply to them. Lily-Rose Depp did exactly that in her widely-mocked Elle interview, dismissing the idea that her famous surname had anything to do with her career. "It's weird to reduce somebody to the idea that they're only there because it's a generational thing," she mused, before adding "If somebody's mom or dad is a doctor, and then the kid becomes a doctor, you're not going to be like, 'Well, you're only a doctor because your parent is a doctor. It's like she forgot that modeling Chanel and going to medical school are, in fact, very different pipelines.

Speaking of Chanel, her 2025 Paris Fashion Week appearance saw an ensemble so aging, it sparked genuine confusion, raising fresh questions about her taste level and whether her style reputation is truly earned. Of course, when your outfits become meme fodder (TikTok users will remember her curious "trench coat buttoned to the top" look), it's difficult to argue that the critiques are unfounded. Granted, she does sometimes get it right (like her celeb castlecore look to influence your medieval-inspired 'fits). But even when this is the case, the effect can oftentimes fall flat because she lacks charisma. As the ever-discerning followers of the Fauxmoi subreddit pointed out, Lily-Rose "never would have booked that Chanel deal without her parents influence." Ostensibly expensive clothes can only do so much if the person wearing them looks like they'd rather be anywhere else.

Compiling a list of the best and worst dressed nepo babies meant looking beyond the designer tags and famous surnames. We assessed selfies, street style, press tour looks, campaign outfits, and red carpet appearances, picking out originality, influence, polish, and a sense of informed, personal flair.

We paid close attention to how their outfits were styled across the board. Were the references consistently thoughtful? Did their looks suggest individuality, or read like a publicist-approved project? Could we cut through the noise of privilege and platform to find actual taste? Social media reactions were factored in, too; if a look sparked memes, backlash, or breathless praise, that mattered.