8 of the Most Questionable Celebrity Street Style Outfits of 2025 (So Far)

Sydney’s year has unravelled with an uneasy equilibrium between triumph and self-sabotage. Her Hollywood ascendancy continues unabated, but she has found herself at the center of a cultural tempest over her partnership with Dr Sqautch to hawk her “bathwater” to thirst (male) fans online — a move critics slammed as setting feminism back decades by reinforcing problematic stereotypes about women as commodities.

Her fashion game this year has been equally erratic. At the 2025 Met Gala, her Miu Miu look had everyone talking. But during her later promotional appearance for her forthcoming Christy Martin film, she stepped out in a tragic graphic tee that could have been pulled from the clearance rack at Forever 21. What’s more, it was complete with a dowdy fit that did her figure zero favors. A cropped baby tee could have salvaged the look, but instead, the whole basic ensemble stripped away her movie star mystique.

It’s undeniably one of the Sydney Sweeney outfits that totally missed the mark, as it left her looking more like someone’s suburban cousin than Hollywood royalty. The girl who can command millions per film somehow managed to look like she got dressed in the dark at Target. Talk about a missed opportunity. 

Is the queen of awkward-chic bitten off more than she can chew? Amelia Dimoldenberg has, for years, modeled herself on as a practitioner of conversational anti-charisma. But irony is difficult to wear — especially when the proportions are off. Deadpan dressing only works when the clothes are in on the joke.

Pictured here at Stormzy’s House Party in Soho, London, Dimoldenberg wears an ensemble that suggests she may be having trouble seasoning her looks. There’s no anchoring piece to carry the look; instead, it hovers indecisively between references. A worn-in graphic tee tucked into cropped capri leggings breaks up the body line at all the wrong places, whilst the oversized bomber — shiny, shrugging — adds bulk without counterbalance. The monochromatic darkness of it all, too, drained her complexion, rendering the outfit less wry than weary.

The shoes deliver the final punchline — and not a good one. There was a time when Maison Margiela Tabis marked their wearer as fashion-literature – someone locked into the avant-garde. But like all once-cult objects absorbed by the Instagram feed, their meaning has curdled. This cult item now signals a try-hard irony, especially in East London, where they’ve become a meme unto themselves. Celebrities are meant to steer the trend cycle, not arrive late recycling what the fashion crowd has already worn to death.

With so much conversation swirling about how the Kardashian-Jenner empire is no longer the cultural force it once was, one might expect a pivot to the more cutting edge. And yet here we are: Kylie Jenner, pictured in head-to-toe neon yellow sweats, offering visual proof that she might still be stuck in her 2010s heyday.

The matching set — a cropped tank, oversized joggers, and an optional hoodie thrown in for good measure — might have passed in 2020, when comfort-core reigned as everyone was dressing for the end times. But in 2025, it’s lazy and dated. The color doesn’t help: neon yellow was already a hard sell in the 2010s, and here it looks straight-up tacky. Loud for no reason and oddly juvenile, it lacks any sophistication or edge.

We’re baffled, too, by the shoes. They’re inexplicably orthopaedic-looking. Taken as a whole, this look confirms what the discourse has already suggested: she embodies a bygone idea right down to the last soulless slipper.

Is Molly-Mae staging a one-woman revival of early-aughts boardroom-to-nightclub fashion? The evidence suggests an unfortunate yes.

Her beige-toned suit is all volume and no balance. The oversized jacket practically swallows her whole, whilst the palazzo pants puddle around her ankles with enough extra fabric to curtain a small apartment. That she managed to move anywhere without tripping over the hem and dragging half the bar with her speaks either to remarkable coordination or sheer dumb luck.

The monochrome palette could have been sleek, striking even. But this time, it washes her out. Without any sharp tailoring to interrupt the fabric’s relentless flow, or a pop of color to break up the monotony, the whole look melts into itself flatly. Her unstyled hair, all too similar in shade to the outfit, didn’t help matters — adding to the impression that the look was assembled without a clear perspective.

It’s been a tough PR year for Blake Lively so far. The rollout of, “It Ends With Us” has been mired in controversy from the start, with fans questioning everything from casting, to tone, to costuming — as well as the messy fallout of the on-set feud between Lively and co-star Justin Baldoni.

This outfit, intentionally or otherwise, seems to absorb some of that tension. The sheen of the leather picks up every paparazzi flash, giving off an unseemly bin-bag glare. The cinched waist of the leather top creates awkward volume, and the wide-leg trousers offer only more mass. It’s an overly heavy look – visually, physically, symbolically.

The “Gossip Girl” star famously (or perhaps infamously) curates her own looks. But it’s safe to say we can bank this one as one of the many outfits that prove Blake Lively needs a legit stylist.

Kourtney delivered the bare minimum on an outing in New Orleans — and not in a cool, satisfying minimalist way. As proved with Kylie before her, the Kardashian-Jenners have always been adopters of casual. But in 2025, the formula is just wearing thin. Pictured here in an black long-sleeved top, black leggings, and black sneakers, Kourtney gives us yet another reminder that the family’s style playbook hasn’t turned a page in years.

It’s not that black can’t be chic. It’s that this particular take on it isn’t even trying. The silhouette is shapeless, the styling nonexistent, the energy entirely fizzled. For someone who’s spent the past few years redefining her brand — wellness guru, rock wife, Lemme mogul — this outfit doesn’t align with any of it.

One can’t help but recall Kim’s withering assessment that Kourtney is “the least exciting to look at.” Suddenly, the aspersion doesn’t seem so harsh.

Remember when Cara Delevingne felt like the future of fashion? Her presence on a runway once implied a certain excitement and irreverence. That time feels distant.

Coachella 2025 was a fashion disaster for everyone there. But few felt the slip more acutely than the “Looking for Alaska” star. Delevingne appeared in a knit tank top the color of oatmeal, brown suede shorts, and rubber platform fisherman sandals. For 2025, the fisherman aesthetic trend was deemed the laidback, coastal vibe your wardrobe needs, but her interpretation of it here sinks with surprising efficiency.

There’s nothing inherently offensive about the pieces individually, but together, they do little more than confirm her inertia. Neutral on neutral, beige on beige, dulling every texture as the entire look blurs. It’s just basic. So, so basic. Where’s that eyebrow-raising supermodel swagger gone?

We return to Coachella, this time via Emma Roberts. There’s an unspoken contract between California’s most performative weekend and its attendees — a promise, however contrived, that fashion will rise to the occasion. The clothes are meant to shimmer, sway, provoke, or at the very least, suggest that someone thought about them. Roberts, however, added nothing to the myth of the modern festival muse.

Her sleeveless white top was stiff and buttoned to the heights. Clinically corporate in tone, it echoed the kind of silhouette often favored by Karoline Leavitt — whose own wardrobe leans heavily on frumpy work outfits that don’t flatter her. Worn with a plain black mini skirt and modest mid-calf boots, the outfit checks the box for function, but offers none of the playfulness the setting calls for.

Should this outfit — along with these other 2025 missteps — prompt a closer look at why celebrity fashion feels increasingly hollow and automated? Possibly. It might be time to ask why the spectacle has dulled.