Pictures of Oprah Winfrey Fashion and Style Throughout Her Career

While Vogue's Anna Wintour famously suggested she "lose a little bit of weight" for her October 1998 cover shoot, it didn't stop Oprah Winfrey from experimenting with fashion trends. The kinks in her personal style have been ironed out in recent times, as the queen of daytime television has left the shoulder pads, gaudy prints and metallic suiting in favour of chic separates in block colours. A keen jzusher, her jewelled (ok, ok, diamond) accessories vamp up her understated outfits. To bid a fond farewell to The Oprah Winfrey Show after 25 years, take a trip down memory lane with Oprah’s most memorable fashion moments.