The dress-over-pants trend has recently made a major comeback. However, don’t worry. The look has evolved significantly from its early 2000s roots. Forget the era of embellished halternecks paired with bell-bottoms and ballet flats, or tight minidresses with skinny jeans and knee-high boots. Today, the style set is prioritizing a more sophisticated, timeless take on the look and emphasizing that elevated sandals are the shoe trend that looks best with the outfit formula. Take Olivia Munn’s recent ensemble, for example.

Spotted in New York this week, Munn showed the most chic way to pull off a dress-over-pants outfit in 2026. She wore an off-the-shoulder, asymmetrical ivory maxi dress that draped and moved effortlessly, paired with tailored black pants with the right amount of slouch. The dress, the modern component, juxtaposed nicely with the pants, the timeless element. To maintain the outfit’s understated elegance, she accessorized with retro shades and open-toe heeled mules.