The AFL WAG struggled to contain her ample assets inside the slashed neckline and repeatedly rearranged the fabric as she posed for the cameras.
Seeing the funny side of her fashion faux pas, the 27-year-old giggled as she held her hands over her chest.
The former David Jones model wore her graduated blonde locks in an edgy, cropped style and paired the simple ivory gown with nude, perspex heels.
Supermodel Kendall jetted into Sydney as Tiffany's guest of honour and stood out from the genetically blessed crowd in a bizarre baby pink mini dress by Ingie Paris.
The unusual satin ensemble was adorned with wide tiered sleeves and a neckline of bubblegum coloured feathers.
Watch Kendall strut her supermodel stuff at the Tiffany launch below!
The Keeping Up With the Kardashians star relies on internationally renowned stylist Marni Senofonte who also works with Beyoncé, and is known for her quirky choice of looks.
She was accompanied on her trip Down Under by hair stylist Jen Atkin and makeup artist Mary Phillips.
According to The Daily Telegraph, the brunette beauty banked a staggering $500,000 AUD for her 24 hour stop in Sydney.