18 Red Carpet Moments That Pushed Fashion Boundaries

Some celebrities play it safe on the red carpet—and then there are the ones who say, “Hold my couture.” From jaw-dropping sheers to architectural wonders that defy gravity (and maybe taste), these 18 red carpet looks didn’t just break the internet—they kicked it in six-inch heels.

1. Lil Nas X in Head-to-Toe Avant-Garde (MTV VMAs)

For the MTV VMAs, he wore a mind-bending creation by Harris Reed that looked like it was spun out of black horsehair and drama. The towering headpiece and tiered hoop skirt brought gender-fluid fashion, camp, and confidence together in one glorious explosion of high fashion.

2. Olivia Rodrigo in Sculptural Black Elegance

Leave it to Olivia Rodrigo to make a “cut-out” look like high art. This sculpted black gown is part dress, part optical illusion, and all drama. It’s serving sultry sculpture with a splash of old-Hollywood lipstick glam. A bold statement from Gen Z’s pop princess.

3. Dove Cameron’s Met Gala Web Fantasy

This webbed, barely-there white masterpiece by Iris van Herpen made Dove Cameron look like an alien queen who crash-landed on Earth to steal fashion week. Delicate, surreal, and somehow futuristic and vintage at the same time—this look belongs in a museum. Or on Mars.

4. Megan Fox’s Spicy MTV Moment

Ah yes, the moment when Megan Fox declared, “Fabric is optional.” She floated down the red carpet in a sheer, shimmering Mugler dress that left little to the imagination and many jaws on the floor. Wet-look hair? Check. Goddess-level confidence? Double-check.

5. Toni Braxton’s Infamous Grammy Slit Dress

Iconic barely begins to cover it. Toni Braxton made headlines at the 2001 Grammys in a white Richard Tyler dress that was 90% side slit and 10% fabric. Sheer nerve, stunning legs, and that Grammy-winning smile made it unforgettable—and pretty much impossible to replicate.

6. Winnie Harlow’s Red Hot Power Statement (Cannes Film Festival)

Model and advocate Winnie Harlow brought the fire in this asymmetrical, high-slit red gown. With a dramatic hood and goddess-like draping, she looked like the final boss in a video game about conquering fashion.