Celebrities With the Wackiest Winter Street Style

Posted by Susy Alexandre on February 6, 2018

This winter, we’ve rounded up the weirdest celebrity street style looks and are bringing you the best of the worst, from downright wacky to just plain tacky. So read on for the must-see fashion blunders from your favourite celebrities, as we scratch our heads and ask – why?

  •  Getty Images
    1 of 15

    Sara Sampaio

    Model Sara Sampaio is stunning in anything she wears, but we just can’t make sense of this chunky knit. Between the extreme cut-outs and bizarre hood-effect, we’re willing to bet this outfit, worn this past January for Paris Fashion Week, was anything but warm. Like so many unusual celebrity trends, we just can’t figure this one out.
  •  Getty Images
    2 of 15

    Jennifer Lopez

    We’re all for the comfy off-duty feels, but this frumpy sweatsuit is doing nothing for the stunning Jennifer Lopez, who looks buried beneath the boxy knits.
  •  Getty Images
    3 of 15

    Bella Thorne

    Getting more eccentric with her fashion choices every day, Bella Thorne was photographed in Utah sporting head to toe red, her small frame overwhelmed by the oversized shaggy red coat she wore over a super-cropped red top, second skin red lace-up pants and snake-effect red booties. It’s no wonder she made it onto our list of the worst celebrity looks of 2017…
  •  Getty Images
    4 of 15

    Gigi Hadid

    Gigi Hadid is one of 32 celebrity kids more famous than their parents, so we can't be too surprised if she's starting to dress like a RHOBH, But with the pinks, yellows, pastels and stripes, this look is all over the place. From Gigi’s sleeping-bag style pink puffer coat to the yellow-striped culottes and pink sneakers, it’s all just too much, and is another one of those trends you should skip this winter.
  •  Getty Images
    5 of 15

    Rita Ora

    Cold weather equals layering, we get it. But why this particular mix of prints and fabrics? That – we don’t get.

    We may not be digging Rita's look, but check out the stars who are nailing it with these photos of the best celebrity winter style to inspire your cold-weather wardrobe.
  •  Getty Images
    6 of 15

    Bella Hadid

    Between the bold cat-eye sunglasses, the red and check print vinyl trench, the bulky boots and baggy jeans, we don’t know where to look! Always a trendsetter, Bella Hadid could easily pull all these trends off – just not all at once.
  •  Getty Images
    7 of 15

    Lady Gaga

    Lady Gaga serves up intergalactic fashion vibes with this electric ensemble. We figure, if anyone can rock this, it’s Lady G – but warning: prolonged exposure to this colour combo may impair your vision! We are loving her pulled back hair and retro glasses, though.

    For more, don't miss 20 style moments that changed everything.
  •  Getty Images
    8 of 15

    Demi Lovato

    We’re all for the cozy oversized knit trend this season, but there’s just nothing flattering about this fuzzy frock. Sorry, we’re not sorry Demi.
  •  Getty Images
    9 of 15

    Haley Bennett

    Haley Bennett is an amazing talent, but this depressingly dark and frumpy outfit is anything but inspirational as she makes her way through JFK.
  •  Getty Images
    10 of 15

    Chloe Sevigny

    Nearly always topping “best-dressed” lists; this one is a rare “fail” from the usual street style star. It may be the overwhelming dose of black against her pale complexion, or the Princess Leia-inspired ‘do – the force was just not with her on this one.
  •  Getty Images
    11 of 15

    Sharon Stone

    The frantic-looking hair, bulky boots, funky scarf and retro shades have Sharon Stone looking completely out of sorts. It’s a lot messier than we’re used to seeing this usually-refined and put together icon.

    Speaking of Sharon Stone, you may also like: 16 celebs with a penchant for younger men.
  •  Getty Images
    12 of 15

    Heidi Klum

    You would think being one of the world’s most famous supermodels, you’d have learned a thing or two about putting together a great “airport outfit.” Not the case for Heidi, who seems tangled up in not only her hair but also her scarf. We’re all for casual attire when travelling, but between Heidi’s bomber jacket and frumpy dress and leggings combo, she just looks sloppy.

    Keep it simple and uncluttered when putting together your own travel-friendly ensemble. And speaking of airports, check out our handy guide on getting through airport security as fast as possible!
  •  Getty Images
    13 of 15

    Christina Hendricks

    More costume than day-wear, this outfit clashes from all directions. There’s fur, mixed prints, bright colours and barely-there pumps that completely wash out her skin tone. From colours to cut, this is all just wrong.
  •  Getty Images
    14 of 15

    Niece Nash

    Niecy, we love you and your bold personality – but this outfit is just too loud! The matching print might have been okay on its own, but teamed up with the long leather gloves, fur scarf and supersized Gucci logo belt? Scale it back, Niecy, scale it wayyy back!
  •  Getty Images
    15 of 15

    Repeat offender: Rita Ora

    The Dr. Seuss look doesn’t quite work in real life, Ora. And we’re afraid to ask how many poor animals went into the making of that ridiculous topper – here’s hoping it’s faux!

    For more, don't miss all the times Kate Middleton and Meghan Markle wore almost the same thing.
  • start over
    Next Gallery

    20 of the Coziest Sweaters for Under $100 in Canada

    More Galleries