10 Best & 10 Worst Celeb Looks From Milan Fashion Week 2023

Part of the big four global fashion week events, Milan Fashion Week is always a star-studded event, both on the runway and in the front row. Taking place twice a year in February and September, with designers debuting their upcoming fall/winter collections at the beginning of the year and their spring/summer designs toward the end of the year, Milan Fashion Week is one of the most highly anticipated fashion events on the calendar. In addition to revealing new luxury brand designs and determining the latest fashion trends, fashion week offers a unique opportunity for celebrities to make a public appearance — and many relish the chance to do so, dressing to show off their own fashion sense and favorite labels.

While many famous folks nail the assignment of serving captivating, ultra-stylish ensembles during fashion week, not every celeb look is a hit. With Milan Fashion Week wrapped for the year, we're taking a look at some of the best — and worst — celebrity outfits worn during the semi-annual Italian event in 2023.

For the Fendi show during Milan Fashion Week, Suki Waterhouse chose a workwear-meets-academia-inspired look that felt a little more drab than fab. The "Daisy Jones and The Six" actor's gray mid-length dress combined two distinct designs that didn't come across as entirely cohesive. The top of the frock resembled a jumpsuit that might be worn by a handyman on the job. The long-sleeved, collared bodice was very utilitarian, and the stitching across the bust and single breast pocket added to the workwear vibe. In contrast, the skirt was giving private school teacher. The pleated material was relatively shapeless, as was the top portion of the dress, and the two elements came together to create an ill-fitting silhouette. Perhaps if the bodice of the dress had been more tailored to Waterhouse's form and the waist cinched higher for an empire cut, it would have been more flattering.

For accessories, the actor opted for a mid-sized black handbag with a woven design and cream-colored heeled mules that took on an abstract feel with their lack of a heel. Her honey-toned hair was down in her usual '70s-style shag, and her makeup included winged eyeliner and rosy lips and cheeks.

Pleats were apparently having a moment at Milan Fashion Week, but like Suki Waterhouse, Naomi Watts' pleated skirt was a bit off-putting. For her Fendi fashion show appearance, Watts chose a bronze blazer and skirt combo that was pretty unflattering on her frame. The boxy jacket could have worked with slim-cut pants to balance out the proportions of her silhouette, but the pleated skirt had the same shapeless fit. Additionally, the below-the-knee hem of the garment made the "King Kong" actor's short stature appear even shorter — which was also emphasized by her choice of shoe. Cute on their own but not in conjunction with this look, Watts opted for a chunky pair of black combat boots with gold detailing and a mid-calf-length shaft. She finished the look with an oversized black woven tote bag, large black sunglasses, and gold hoop earrings, wearing her short hair straight and adding a classic pink lip.

If we could edit this outfit, we would suggest cropping the blazer just below the bust, lengthening the skirt's hem to hit Watts' ankles while going for a high-rise waist that bared a strip of the actor's stomach between the two pieces, and switching the boots for a pointed-toe heel. But who do we think we are, luxury fashion designers?

In contrast to Hunter Schafer's enchanting academia-inspired outfit, Rosalía donned a look of the same aesthetic that doesn't have us feeling nearly as excited. For the Prada fashion show, the "Beso" singer went with a demure ensemble that included a white button-down shirt with a gray sweater vest overtop. Though it's a bit boring, the cut of both garments does flatter Rosalía's frame, emphasizing her hips and shoulders. She added a lighter gray maxi skirt to the look, which was, again, leaning on the duller side of the fashion spectrum. It's definitely not the worst outfit we've ever seen; it's just kind of ... blah, compared to the many other gorgeous celebrity looks worn during Milan Fashion Week.

For her all-black accessories, Rosalía chose a Prada bucket bag, pointed-toe heels, and 2000s-style sunglasses. Where the singer really lost us was with the Y2K cloth headband pulling her espresso-colored tresses back from her face. It not only feels like a really random accessory with the rest of the outfit, but it also just doesn't give high fashion. Overall, the look just falls sort of flat — it's certainly not egregious, but it's not one to rave about either.

Demi Moore embraced "The Great Gatsby" of it all for her appearance at the Versace runway show during Milan Fashion Week. Rocking Jay Gatsby on the top and Daisy Buchanan on the bottom, the "Ghost" icon definitely wasn't afraid to go bold, and we commend her for that. But did the 1920s-inspired outfit work? We're not entirely sure. What we do like is Moore's blazer and shoes. She went with a silky black jacket with structured shoulders and opulent gold embellishments sprawling across select portions of the garment. Moore embraced the plunging neckline of the blazer by wearing nothing underneath, showing off her chest without getting too risqué. Her heels — gold pumps with dainty straps — were simple but fashion-forward.

Where Moore really lost us is with her pants. There are a few things we don't quite like about them — first of all, the tiered layers of beaded gold fringe are just ... a lot in general. While this look works beautifully in a flapper dress, it doesn't transition super well in pants. Second of all, the high-waisted cut of the bottoms produced a bulging effect in the lower section of Moore's jacket. Because the fringe layers were so voluminous, they pushed the bottom of the blazer out, which created an unflattering shape at the actor's midline. Points for her stunning silky mane and small dog as an accessory, though!

Miss Blair Waldorf ... What's going on? "Gossip Girl" alum Leighton Meester attended Milan Fashion Week's "Calzedomania: A Legs Celebration" event, and her outfit doesn't feel like one her teen drama character would approve of. Anyone familiar with Blair Waldorf knows this look would likely get her signature sneer of distaste and a comment about waitressing in Brooklyn, let's be honest. It's another one of those looks that isn't horrible, but it just doesn't stand up to the incredible ensembles worn by other celebs. Meester's updo and the halter cut of her mini dress are definitely reminiscent of a diner uniform — but like, make it fashion? We do like the stone color and fit-and-flare silhouette of the garment, but something about the formal vest-style bodice just doesn't work. 

Meester paired sheer black pantyhose and black patent leather pumps with the look, which are nice together but create a bottom-heavy effect in combination with the pale dress and the actor's mostly bare upper body. She accessorized with a mini red handbag and matching manicure, which we do like, and she rocked a classic "your skin but better" makeup look. A cherry red lip would have been a nice touch with her red accessories, but Meester opted for a glossy pink instead.

Julia Fox is never boring during fashion week, that's for sure. Curating a look as bizarre as her's tend to be, the model gave the stacked belt concept a try in Milan — but in comparison to Kim Kardashian's high-fashion look, Fox's leaves much to be desired. Her disjointed outfit had three distinct elements, one of which was her thigh-high denim boots. The pointed-toe shoes featured a slouchy fit and, all things considered, aren't the worst denim boots we've ever seen. The second element of Fox's ensemble was her leather belt skirt. Where Kardashian's skirt was modern and sleek, Fox's was chunky and clunky with brown leather belts your grandpa probably wore in the 1980s. The makeshift skirt was also ultra-low-waisted, which made Fox's legs look really short in combination with her boots.

Lastly, the model went with a monochromatic white vibe for the top half of her outfit. She started with what looked like an upside-down cami with lace trim lining the hem (the neckline?) and unfastened garter belt clips in place of spaghetti straps. Fox topped the confusing shirt with a leather moto jacket, which featured an undone belt around the hem and a fastened belt around the neck. She finished the look with a lunchbox-style crossbody bag and went with avant-garde pink makeup to match her magenta-colored hair. Julia Fox nailed her signature outrageous outfit aesthetic, we'll give her that!

Noah Cyrus attended Fendi's runway show during Milan Fashion Week, and she debuted a style that was much more experimental than anything she'd previously worn — mostly due to her alien-esque look. The "July" singer's outfit for the fashion event wasn't the worst ever, but in comparison to other celebrity styles, it was a bit of a flop. In fact, German blogger Leonie Hanne wore the same dress in a different color at the show, and the tailoring and styling of her look were much more fashionable than Cyrus' rendition. The musician chose a blush-colored single-shoulder gown, and she opted to leave the hem long enough to drag on the floor. The sateen fabric was slightly ruched around the bodice and hips, then transitioned to a cascading A-line skirt. A river of fabric flowed down the center of the dress, extending from the single halter-style strap wrapped around one side of Cyrus' neck. 

The singer accessorized with a small white handbag, and she left her arms bare to display her tattooed skin. Cyrus' raven mane hung long and straight, and her makeup had an extraterrestrial effect. Her brows were shaved off, and her cheeks and eyes were heavily dusted with pale pink blush. Cyrus' eyes were mascara-free but lightly lined, giving her a slightly off-putting Mona Lisa-esque look.

Uma Thurman is an absolute icon, but her Milan Fashion Week look at the Ferragamo show was not the stuff of fashion legends. The "Kill Bill" actor chose to wear a matching set made of pale mustard-colored suede. The silhouette of the monochromatic top and bottom is nice-ish — we like the way it hugs Thurman's frame without being tight — but some of the tailoring looked a little awkward. For starters, the skinny fit of the pants is dated, and not in a cool retro way, at least at the moment. The ankle-length hem with the slit up the inside of the leg is flattering, but the crotch area of the trousers makes us cringe. The high-waisted pants were bunching around Thurman's groin, which is never a desired effect, and it made the seamless fabric take on a diaper-like look. We have a similar hangup with the top: the cut is okay and we like the turtleneck, but the bust appears deflated due to the flat shadow beneath the actor's chest.

Thurman's accessories, hairstyle, and makeup were a win though. Her strappy black heels are gorgeous, her tiny black handbag is on-trend, and we love her Twiggy-inspired hair swoop. The movie star's chunky gold earrings are stunning as well, and we love her understated yellow eyeshadow.

Ashley Graham's dress for the Moschino show during Milan Fashion Week was nothing if not unique. The supermodel wore a ballroom-style gown that seemed to take heavy inspiration from the life of a chef. Yes, you read that right. While the skirt was giving classic princess vibes thanks to its tiered layers of ruffled tulle, the top made us giggle and scratch our heads. The bodice and top-most layer of the dress look like a chef's coat. Not only is the silhouette uncannily similar, but lining both sides of the bodice are 10 pieces of gold cutlery. Cutlery, as in spoons, forks, and knives. 

While there's likely a fascinating story behind the unusual design, it doesn't have us praising Graham as a fashion icon. The model finished the look with gold chandelier earrings, a Cinderella-style updo, and makeup that included a metallic winged eyeshadow and a '90s-inspired lip.

We usually love Jodie Turner-Smith's outfits, but the ensemble she wore to Milan Fashion Week's Gucci show was a miss for us. The busy look included a variety of statement pieces, and while they all matched in a way, they also clashed by fighting one another for attention. The "Murder Mystery 2" actress wore a metallic gold and black tiger print button-up that featured utility pockets and an oversized fit. Turner-Smith's waist was cinched with a patent black wide-band belt fastened with a huge acrylic buckle. She swapped pants for nearly hip-high black leather boots that had a pointed toe, stiletto heel, and laces from the upper to the very top of the shoes.

Turner-Smith accessorized with a studded black handbag, a diamond-encrusted Cuban link necklace, a variety of rings and earrings, and a black Kufi hat. The actor finished the look with makeup featuring rose and terracotta tones, as well as thick winged eyeliner.