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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.

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1.

March 30, 1987.
Jim Smeal / Ron Galella Collection

March 30, 1987.

2.

January 1, 1987.
Time Life Pictures/DMI/Time Life Pictures / Getty Images

January 1, 1987.

3.

February 17, 1989.
Ron Galella, Ltd. / WireImage

February 17, 1989.

4.

January 24, 1986.
Ron Galella, Ltd. / WireImage

January 24, 1986.

5.

December 17, 1987.
Jim Smeal / WireImage

December 17, 1987.

6.

November 7, 1986.
Ron Galella, Ltd. / WireImage

November 7, 1986.

7.

June 30, 1987.
Ron Galella, Ltd. / WireImage

June 30, 1987.

8.

October 22, 1988.
Ron Galella, Ltd. / WireImage

October 22, 1988.

9.

June 1, 1988,
Ron Galella, Ltd. / WireImage

June 1, 1988,

10.

June 23, 1992.
Ron Galella, Ltd. / WireImage

June 23, 1992.

11.

June 1, 1993.
Jim Smeal / WireImage

June 1, 1993.

12.

February 1, 1992.
Time Life Pictures/DMI/Time Life Pictures / Getty Images

February 1, 1992.

13.

September 8, 1990.
Jim Smeal / WireImage

September 8, 1990.

14.

April 24, 1987.
Ron Galella, Ltd. / WireImage

April 24, 1987.

15.

January 27, 1993.
Ron Galella, Ltd. / WireImage

January 27, 1993.

16.

March 13, 1986.
Jim Smeal / WireImage

March 13, 1986.

17.

January 23, 1986.
Ron Galella, Ltd. / WireImage

January 23, 1986.

18.

January 1, 1992.
Time Life Pictures/DMI/Time Life Pictures / Getty Images

January 1, 1992.

19.

January 1, 1988.
Time Life Pictures/DMI/Time Life Pictures / Getty Images

January 1, 1988.

20.

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

21.

February 25, 1989.
Ron Galella, Ltd. / WireImage

February 25, 1989.

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