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90s Boots or booties : These, especially short lace up boots, were the trendiest winter footwear

While combining these elements can create a stylish, casual look, context matters

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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