Figuring out what to wear with leggings is a key part of the millennial existence. If you’re over the age of 30, the athleisure staple has likely carried you through every stage of your life, from high school to working from home. Even as your tastes changed, your favorite leggings remained a constant. The way we style them, however, has evolved. They’ve gone from something to wear to the gym or around the house to a street-style hero—with the right high heels and gold accessories, of course.
While the critical eyes of Gen Z might have briefly made us question our lifelong allegiance to the wardrobe staple, that was a blessing in disguise: Now, in 2026, we’re much better at wearing leggings. Whether you’re dressing for the gym, the office, or a dressy evening, it’s easier than ever before to make leggings look downright chic. (Even Zoomers will approve of the formulas below.) Read on for insider-approved outfit ideas to help settle what to wear with leggings—and keep you right on trend for fall 2026.
With a dramatic jacket for a night out
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