Jenner stomped out in New York City wearing eye-catching white booties but found a much edgier style statement to make by going braless under a delicate white lace-up corset dress.
Unfortunately she suffered a slight wardrobe malfunction when the semi-sheer fabric around the bodice partially exposed her body.
That same day she made an appearance at the Veuve Clicquot Polo Classic wearing the same boots teamed with an off-the-shoulder Dolce & Gabbana dress.
The green velvet mules feature faux fur puff embellishments and retail for $650 on Barneys.com.
Meanwhile, the no-bra look was in full effect for Alessandra Ambrosio on Friday when she helped launch Spanish footwear brand XTI’s new line in Madrid.
The Victoria’s Secret Angel donned a white halter-top blouse with green trousers and XTI’s gold sandals. The shoes incorporate a chunky block heel and a glittery band across the toe. They’re available on xtistore.es for around $45.
Click through the gallery to view more celebrity wardrobe malfunctions.