black dress with white hearts Paris Georgia Heart A sharper vintage mood Allegra K Women's Heart Mesh

On this day in fashion.com

Though Winfrey has gravitated toward mature, ladylike looks for most of her career, one of my all-time favorite Winfrey looks is the kind of thing I can easily imagine an arty twenty-something in Brooklyn donning for a poetry reading

Complete the look with black heels and gold jewelry for a stunning and sophisticated outfit perfect for any formal occasion

With its western-style crown and 2 town-friendly brim, the Open Road Straw easily transitions from country to city, and looks equally sharp on a woman or a man

Winged liner and matte red lips are both bold choices, but they somehow work perfectly together without being too much