Heidi Klum, 49, and her daughter Leni, 18, attend Harper's Bazaar ICONS event in NYC

Kendall Jenner enjoys night out with on/off beau Devin Booker in NYC

Kendall Jenner Holds Hands With Devin Booker at a Friend's Birthday Party in NYC

Irina Shayk & Daughter Lea, 5, In NYC Amid Romance Rumors With Ex Bradley Cooper