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.

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