"Reunion on ice with Trey Phillips," Conrad, 26, captioned a shot of her and Phillips smiling for the camera. In another photo of a skating rink and Christmas tree in NYC, she wrote, "Ice skating in the park . . ."
The always-fashionable Conrad dressed up in a cute winter hat and scarf for the outing, but suffered an unfortunate wardrobe mishap along the way.
"Just left my new favorite hat in a cab," she tweeted. "It will be missed."