Kylie Jenner Just Wore A Dress Over Leggings & NGL, I’m Kind Of Into It

Kylie Jenner, Fashion Girl, never shies away from a sartorial risk — especially not for date night with beau Timothée Chalamet. On Saturday, the Khy founder joined the actor in New York following his Saturday Night Live hosting gig for a celebratory dinner with the cast.

Though she wore a low-key all-black ensemble, nothing about her was basic. In fact, Jenner rocked not one, but two typically controversial styling techniques — and absolutely slayed.

Kylie’s Elevated LBD

Playing the role of chic girlfriend, Jenner wore a fitted mini dress to the SNL afterparty. Her LBD featured a saucy asymmetrical neckline that draped off one shoulder. Instead of going the revealing route with a bare leg or tights, however, Jenner wore opaque, shiny black leggings underneath.

The Kylie Cosmetics founder merchandised her all-black ensemble with even more inky accessories, including sunglasses and a simple top-handle handbag. On her feet, the Kardashians star wore heeled sandals with minimal straps over her tights.

She Committed A Fashion Crime & Got Away With It

Back in the chaotic early aughts, dresses were worn with pants consistently (cc: Ashley Tisdale). And much like the rest of the trends from the ’00s, the look was utterly polarizing. It was quickly dubbed a faux pas and hasn’t been touched by the fashion set since.

The recent Y2K renaissance, however, has unleashed questionable styling choices of decades past — including the contentious dresses-over-pants trend. Jenner, however, managed to make the look feel completely modern with a monochromatic color palette and contrasting textures.

Karla Lopez, Bustle Digital Group’s Associate Fashion Editor, confirms that leggings under dresses have historically been considered “taboo,” especially in more formal settings. This attitude, however, is changing.

Embracing Leggings: “The comfort and flexibility offered by leggings appeals to the modern, on-the-go consumer, contributing to their widespread adoption in high fashion. This Spring 2024 season, designers like Phillip Lim, Alaïa, and Blumarine showcased how to give off an aura of classiness while wearing leggings.” — Lopez

It wasn’t the only controversial styling choice of the night, either. Wearing tights with open-toe sandals — her favorite styling trick as of late — was another fashion risk that paid off.

Timothée Went Utterly Casual

Meanwhile, the man of the night slipped into something more colorful and a lot more casual. Chalamet wore a lilac jacket with a shearling lining over a lavender hoodie with an orange block print.

Keeping the rest of his look understated, the Dune star swapped color for grays and blacks. He wore gray jeans, black sneakers, and a matching baseball cap.

Say what you will about this pairing, but you can’t deny: they look good together.