Lindsay Lohan’s Confusing Y2K Look Featured the Pants I’m Living in for the Next 6 Months

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What’s your take on dresses over pants?

For the most part, we’ve moved on from the nostalgic Y2K trend, swapping it for the coquette aesthetic or something a bit more quiet luxury, but there’s one niche staple of the 2000s that’s still going strong, and I kind of, sort of, love it.

The dress-over-pants look was not something I ever expected to come around to. When Katie Holmes first stepped out in a mini dress she layered over a pair of vintage-inspired jeans, I thought, “Is nothing off limits?” But the more celebrities rocked the combo — from Priyanka Chopra to Kylie Jenner — the more I started to warm up to it. And, as of yesterday, I can officially say I’ve been converted all thanks to Lindsay Lohan.

When the actress stepped out in New York on March 7, she made me do a double take because her look was rather confusing. Rocking a beige overcoat and a flowing, drapey all-white ensemble, her outfit leaned so breezy and light, it almost made me forget it’s still technically winter. But, upon further inspection, I realized this wasn’t just an oversized top and pants; she was wearing what looked to be a mid-length dress over her wide-leg trousers.

Veronica Beard Octavia Stretch-Linen Wrap Dress

$598 at veronicabeard.com

$598 at neimanmarcus.com

Everlane the Way-High Drape Pant

$90 at everlane.com

Never did I expect an intersection of the quiet luxury trend with Y2K fashion, but here we are, and I’ll be the first to say, I love it. Lohan’s dress-over-pants outfit veered away from the rigid, tight stylings we’ve seen before, and instead, offered elegant draping and movement. The top, which featured elements of a wrap dress and what looked like a button-down tied around the waist, was casually fastened, creating a relaxed V-neck and a front slit at the legs. Then, perfectly tailored trousers poked out underneath, which were put on full display as she walked and her dress swayed in the wind. The entire look was truly seamless — it’s not really clear where one piece ends and the other begins, but that’s part of its appeal.

While I love the entire set, I’m obsessed with Lohan’s easy, breezy white trousers. They’re just the right amount of oversized — roomy without being baggy — with tailoring and pleats that elevate the style, and are bottoms I could see myself living in this spring and summer. With a simple white T-shirt, you get that same cohesion of Lohan’s look in a more casual way. However, you can just as easily dress them up with your favorite blouse or structured blazer. Plus, they’re versatile enough for the office, dinner dates, and even beach vacations. I don’t own a pair yet, but I’m fully prepared to never take them off.

Lohan has convinced me luxe, flowy white trousers are the item every spring wardrobe needs (better yet if you style them with a dress on top). Shop more pants inspired by her all-white look, below.

Get the Look:

Madewell the Harlow Linen Wide-Leg Pants
Shop now: $88; madewell.com

Hoover Wide-Leg Linen-Blend Pants
Shop now: $30 with coupon (Originally $33); amazon.com

Banana Republic Carmel Pleated Wide-Leg Pants
Shop now: $78 (Originally $130); bananarepublic.gap.com

Good American Good Skate Pants
Shop now: $169; nordstrom.com

Funyyzo Wide-Leg Pants
Shop now: $41; amazon.com

Gap 365 High-Rise Linen-Cotton Trousers
Shop now: $90; gap.com

J.Crew Sydney Linen-Blend Pants
Shop now: $115 (Originally $148); jcrew.com

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