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As a rule of thumb, sleeker shoes go better with slimmer jeans, and chunkier boots pair better with baggier jeans

L: Oscar de la Renta Asymmetric Wool-Blend Dress, $1,120.50

The V-neckline is one of the most universally flattering necklines out there, especially over 50, because it lengthens the neckline and draws attention upward

Stuff the neck cavity loosely and either skewer or sew the skin over the stuffing

Cropped pants, full-length slacks, and skirts in solids or muted patterns

Transitional Casual Autumn Outfit With Sweater Vest And Sandals Sandals with a block heel with trousers or jeans transition for casual outfits (I saw this in Rome, too)