From ill-fitting frocks to mismatched accessories, we break down the week’s worst celebrity looks every Friday.
We’re in the dog days of summer and these stars are in the doghouse of fashion.
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1 / 20
Ariel Winter
This is like a cross between Kim Kardashian and Jessica Simpson, circa 2008. You would've only been 10 then so maybe that's why you didn't know any better?

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2 / 20
Ansel Elgort
We're not sure if the fault lies with him or his stylist but it's like he was dared to wear this clusterf*ck of rejects and Ansel would never turn down a dare.

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3 / 20
Peyton List
Mid-thigh up, it's kind of cute. Everything below that, however? Nothing but net. In the worst way possible.

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4 / 20
Jaden Smith
No amount of flowers on this jacket could cheer this dude up. That's right, even he's saddened by this ensemble.

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5 / 20
Kristina Kane
The boldly patterned pants aren't cropped short enough to go with those strappy flat mom sandals. All we want to do is hack off three inches from them OR put her in flip flops.

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6 / 20
Andra Day
The wide-leg romper made from material found in the Fabricland clearance bin is only made worse by the clay-coloured lipstick she chose.

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7 / 20
Chris Pine
Not since 90210 have we seen a 'do this pouffy or a look this smoldering. Sadly, his look doesn't get any better once you pan down to the wannabe-but-not-quite Hammer pants.

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8 / 20
Ariel Winter
Those are a lot of stripes, though we admit that's not all we're seeing. Guess she's flaunting it now that she's got it? Still, not as bad as that earlier outfit.

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9 / 20
Yolanda Ross
The colour is gorgeous but the weird draping and unstoppable linen-like wrinkling is too annoying to ignore.

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10 / 20
Rosie Perez
Girlfriend is drowning in this thing. Next time, Rosie, an LBD — emphasis on the L.

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11 / 20
Debbie Harry
Oh, Debbie, your choice in bra was not ideal. And paired with pink mules (shudder), a cheetah print sweater and a hat that only belongs on a beach? NO.

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12 / 20
Jaden Smith
What is with this kid and his penchant for shopping in the big and tall section of the big boys' department? But three sizes smaller and this still wouldn't work.

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13 / 20
Jenna Coleman
She's set to play Queen Victoria in an upcoming miniseries but there's nothing royal about this mess of a dress.

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14 / 20
Jessica Szohr
Her shoe game is on point (heh, see what we did there?) but there's something off about the rest of the look. Plus, all we want to do is run our fingers through those tightly wound curls. That 'do is too ... done.

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15 / 20
Ashley Smith
A flowy skirt with that top OR a flowy top with those shorts. Together, it's not enough.

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16 / 20
Bradley Cooper
It's literally like he rolled out of bed. LITERALLY. No excuses for this rumpled disaster.

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17 / 20
Tia Mowry
We don't get it.

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18 / 20
Ally Hilfiger
Try as she might but that book isn't big enough to hide what's going on with her homage to Elvira.

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19 / 20
Christie Brinkley
This giant doily is anything but beautiful.

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20 / 20
Anna Wintour
Yep, we're saying it: not good, Ms. Wintour. Especially the shoes. We're shocked and, not gonna lie, a little disappointed.
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