Milan Fashion Week: Vote on the best and worst-dressed celebrities, from Dakota Johnson to Charli D’Amelio

It seems like all of the biggest celebrities are in Italy for Milan Fashion Week, with everyone from supermodel Naomi Campbell to Emmy-winning actress Julia Garner stepping out in stylish looks. Showcasing womenswear Spring/Summer 2025 pieces between Sept. 17 to 23, this year’s event wraps up on Monday.

Fashion shows from household names like Prada, Hugo Boss and Gucci have taken over numerous venues in the city, with look after look leaving people’s heads turning in awe and wonder. Even viral influencers like TikTok’s beloved (or infamous?) Nara Smith and Chicken Shop Date host Amelia Dimoldenberg strutted out to make an appearance.

When it comes to the fashion seen on stars off the runway, there’s been numerous outfits that showcase full-on glamour — and others that seem to miss the style mark. So, we’re looking at some of the best and worst-dressed celebrities at Milan Fashion Week, and asking you, Yahoo Canada readers, to vote on each look.

At the Gucci fashion show, stars like Dakota Johnson and Jessica Chastain brought out the florals, while other big-name stars like Carey Mulligan, Pia Wurtzbach and Olivia Palermo turned up the heat in all-black ensembles. On the other hand, celebrities like Ashley Graham, Joey King, Charli D’Amelio, Poppy Delevingne and Irina Shayk played with muted colours — but didn’t necessarily win best dressed at their events.

Who would you vote as the best and worst-dressed celebrities at Milan Fashion Week so far? While more looks are sure to pop up over the weekend, read more about the outfits we’ve seen this week and cast your vote below.

BEST DRESSED: Dakota Johnson

Dakota Johnson sat front row at the Gucci womenswear show — beside BTS member Jin, who made his Milan Fashion Week debut — looking stunning on Friday. The 34-year-old actress wore a white sheer dress that featured an embroidered pattern of daisies. She paired the see-through piece with white underwear and an oversized black leather jacket, accessorizing with a Gucci Jackie mini handbag and slingback heels.

WORST DRESSED: Ashley Graham

Ashley Graham layered up for her arrival at the Tod’s fashion show on Friday, but ultimately looked a bit uncomfortable for the event. The 36-year-old model opted for a menswear-inspired look that featured a long brown coat from the brand over a blue pinstripe shirt and tan trousers. She accessorized with dark brown loafers and the Tod’s Timeless Flap Bag in a brown leather.

BEST DRESSED: Carey Mulligan

Carey Mulligan exuded chic confidence at the Prada show on Thursday, sitting front row next to Maya Hawke. The 39-year-old actress wore a black long blazer paired with a pencil skirt for the event; she accessorized with classic black heels and deep black sunglasses, as well as items from the fashion house including a white belt and a Galleria Saffiano leather bag.

WORST DRESSED: Joey King

Whomever is trying to make wrinkled clothing a fashion trend needs to re-evaluate their decisions. Joey King missed the mark with the grey long-sleeve dress she wore at the Max Mara show on Thursday, as it was in desperate need of a good steam. The piece featured a collared top, a side cut-out and a thigh-high slit. The 25-year-old actress accessorized with black strapped heels and an extra-small black leather clutch from the brand.

BEST DRESSED: Pia Wurtzbach

Pia Wurtzbach opted for a sultry casual all-black look at the Hugo Boss fashion show on Wednesday. The 34-year-old Miss Universe 2015 winner wore an oversized blazer that was left unbuttoned to show off an unbuttoned shirt and a lace bra. She paired the look with tights, pointy heels and sunglasses, along with a silver metallic shoulder bag from the brand.

WORST DRESSED: Charli D’Amelio

Charli D’Amelio played with mixing and matching for the Prada fashion show on Thursday, but her look fell flat when it came to style. The 20-year-old influencer wore a black leather turtleneck jacket, paired with a long grey skirt that exposed a white drawstring at the waist. She accessorized with violet purple sunglasses, matching pointed-toe shoes and a grey Prada Buckle hand bag.

BEST DRESSED: Jessica Chastain

Jessica Chastain shined in florals at the Gucci fashion show on Friday. The 47-year-old actress wore an off-the-shoulder white and green dress that featured a pattern of daisies. She accessorized with black slingback heels, as well as square-framed sunglasses from the fashion house and a Gucci Jackie mini handbag.

WORST DRESSED: Poppy Delevingne

Poppy Delevingne went for a mixture of, well, browns for her outfit at the Philosophy Di Lorenzo Serafini fashion show on Thursday. The 38-year-old sister of famed model Cara Delevingne wore a long-sleeve top tucked into wide-leg trousers. Her ensemble featured a one-shoulder cape, as well as sandals for accessories.

BEST DRESSED: Olivia Palermo

Olivia Palermo looked chic at the Vogue Italia x Martini L’Aperitivo event on Tuesday. The 38-year-old reality TV star wore an all-black ensemble featuring a long sheer and striped dress, high-waisted underwear and a dramatic long feathered coat. She also wore thigh-high boots to accessorize.

WORST DRESSED: Irina Shayk

Irina Shayk also opted for a sheer all-black ensemble, but one that felt a little underwhelming for such a high-profile event. The 38-year-old model, who was dating Tom Brady until reportedly earlier this year, wore a lingerie-like gown for the Vogue Italia 60th Anniversary x Ray Ban event on Tuesday. The goth-inspired Alberta Ferretti gown featured lace detailing throughout.

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