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With Matt Lauer as Jerry Senfield, Al Roker as "Family Matters" own Steve Urkel, Savannah Guthrie as Demi Moore's iconic Vanity Fair cover, Dylan Dryer as Baby Spice, Tamron Hall as Julia Roberts in "Pretty Woman" and Jenna Bush Hager as none other than her grandmother, Barbara Bush, there were lots of throwbacks on the Plaza

When choosing your hue, consider your skin tone and the venue lighting

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Case in point: she donned this slinky sheer number for the 17th Annual CFDA Awards in 1998

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