Skip To Content
    Posted on Jan 29, 2014

    21 Fantastic Oprah Winfrey Outfits From Her Early Career

    A look back at some fashion moments that should probably remain in the '80s and '90s.

    1.

    Jim Smeal / Ron Galella Collection

    March 30, 1987.

    2.

    Time Life Pictures/DMI/Time Life Pictures / Getty Images

    January 1, 1987.

    3.

    Ron Galella, Ltd. / WireImage

    February 17, 1989.

    4.

    Ron Galella, Ltd. / WireImage

    January 24, 1986.

    5.

    Jim Smeal / WireImage

    December 17, 1987.

    6.

    Ron Galella, Ltd. / WireImage

    November 7, 1986.

    7.

    Ron Galella, Ltd. / WireImage

    June 30, 1987.

    8.

    Ron Galella, Ltd. / WireImage

    October 22, 1988.

    9.

    Ron Galella, Ltd. / WireImage

    June 1, 1988,

    10.

    Ron Galella, Ltd. / WireImage

    June 23, 1992.

    11.

    Jim Smeal / WireImage

    June 1, 1993.

    12.

    Time Life Pictures/DMI/Time Life Pictures / Getty Images

    February 1, 1992.

    13.

    Jim Smeal / WireImage

    September 8, 1990.

    14.

    Ron Galella, Ltd. / WireImage

    April 24, 1987.

    15.

    Ron Galella, Ltd. / WireImage

    January 27, 1993.

    16.

    Jim Smeal / WireImage

    March 13, 1986.

    17.

    Ron Galella, Ltd. / WireImage

    January 23, 1986.

    18.

    Time Life Pictures/DMI/Time Life Pictures / Getty Images

    January 1, 1992.

    19.

    Time Life Pictures/DMI/Time Life Pictures / Getty Images

    January 1, 1988.

    20.

    Ann Clifford/DMI/Time & Life Pictures / Getty Images

    21.

    Ron Galella, Ltd. / WireImage

    February 25, 1989.

    Nostalgia Trip

    Take a trip down memory lane that’ll make you feel nostalgia AF

    Newsletter signup form