The Best Flat Boots to Keep You Grounded This Winter

Finding the perfect flat boot can transform not only your outfit but also your mood—practical and grounding, a more masculine boot style is the perfect piece to carry you from day to night. I always turn to a flat boot to toughen up a feminine silhouette: a tip I learned from stylist and shoe designer extraordinaire Tabitha Simmons, who styled Kendall Jenner for the November issue in a stunning Marc Jacobs coat and voluminous dress paired with lug-sole boots by Alexander McQueen. “The contrast between the feminine, vibrant colors in the dress and the tough, structured silhouette of the boots gave the look a bit of an unexpected edge,” Simmons says. On her personal boot style, she adds: “I love to style boots with a daintier heel with a sleek pair of trousers or jeans for a more relaxed look that can also take you from day to night.”

From the streets of New York to slopeside in Aspen, these are the best boots to ground you through the holiday season—and beyond.