3 Chic Ways To Style The Early Aughts’ Most Divisive Trend

Here’s how to put a new spin on the old dress-over-jeans combo.
By Jillian Vieira
3 Chic Ways To Style The Early Aughts’ Most Divisive Trend (Background: iStock)

Katie Holmes recently sent the internet into a sartorial tailspin when she stepped out on the red carpet in a strapless satin mini dress worn over baggy, frayed-hem jeans.

Katie Holmes on the red carpet wearing a mini navy dress over pants. (Photo: Getty Images)

Turns out the Y2K trend of sporting a dress or tunic over pants is just as polarizing as it was two decades ago. Back in the early aughts, Anne Hathaway, Zoe Saldana and Jessica Alba all sported the look, but ultimately it was as fleeting as our penchant for baby tees and low-rise jeans.

The controversial red carpet moment begs the question: Can the layered look be updated for a new decade? The answer is a resounding yes. With a few tweaks and fresh silhouettes, the styling technique can give your wardrobe a whole new feel. Here’s some inspiration on how to try the modern dress-over-pants look with pieces you likely already have in your closet.

3 Chic Ways To Style The Early Aughts’ Most Divisive Trend

Monochromatic mood

The easiest way to sport a dress over pants without veering into Y2K overload? Bet on black. The foolproof hue gives you the green light to get creative with bold silhouettes. Pro tip: Play with textures—here, we’ve paired soft, drapey silk and edgy, shiny faux leather—to add visual interest to a monochrome moment.


(Banana Republic silk dress, $250, Babaton pleated pant, $148, Open Edit slingback pumps, $75, Suetables chain hoops, $35, Lambert vegan handbag, $115,

3 Chic Ways To Style The Early Aughts’ Most Divisive Trend

Easy elegance

If your style is classic and polished, you can still partake in this tricky trend with elevated pieces—and a neutral palette—that feel familiar. Take this 9-to-5-appropriate look, for example: a waist-cinching denim mini paired with flowy ecru trousers deliver just the right amount of contrast to pull it all together. Throw in a trove of accessories and you’re primed for boardroom style success.

(Madewell denim mini dress, $185, Mango flowy trousers, $70, Maguire heeled boot, $245, Pandora chain-link bracelet, $250, Matt & Nat satchel, $150,

3 Chic Ways To Style The Early Aughts’ Most Divisive Trend

Great lengths

If you’re still not sold on the dress-over-jeans combo, take a cue from this chic combo and experiment with proportions. To ease into the trend with just a peek of pants, opt for a flowy dress that features a long, ankle-length cut and a side slit, and slip on a pair of dark-wash denim underneath (a straight cut will balance out the volume up top).

(H&M voluminous satin dress, $38, Everlane jeans, $153, La Daje oversized statement ring, $95, Aldo ankle boot, $130, Simons slouchy bag, $175,


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