Jessica Stam

Jessica Stam. Photos: Astrid Stawiarz/Getty Images | Jemal Countess/Getty Images

Uptown: Tommy Hilfiger Prep World NYC Pop-Up House
Look: The 25-year-old print and runway model, who's known for her piercing blue-gray eyes, embodies all-American beauty with a fresh face, natural brows, straight strands and bubblegum pink pout.

Downtown: Summer With Off Duty Party 2011
Look: Stam appears lit-from-within in illuminating eye makeup, dewy skin, rose lip gloss and naturally wavy hair accentuated with a braid at the crown.