Chrissy Teigen Wore This Dated Legging Outfit in LA

Chrissy Teigen wears black heeled ankle boots, black leggings, a striped button-down shirt, a black Gucci crossbody bag, a black hat, and a white sports bra.

You can always rely on Chrissy Teigen to make a stylish entrance. Known for her impeccable off-duty fashion sense, she often flaunts a variety of maxi dresses, mini skirts, and knee-high boots. However, during a recent outing in L.A., Teigen surprised everyone by ditching her usual pieces for a combination of leggings and boots.

Yesterday, the model and TV personality was spotted running errands, hauling around a Hulken Bag in a blue striped button-down shirt, a white sports bra, and a Gucci bag, all styled alongside black leggings and heeled ankle boots.

On Chrissy Teigen: Gucci bag; Hulken Bag ($115); Bottega Veneta Canalazzo Booties ($1300)

Throughout the years, leggings have become a casual essential that can be worn for activities other than working out (see Miu Miu’s F/W 23 and Max Mara’s F/W 24 shows for inspiration). However, it was Teigen’s unique styling approach that made the bottoms feel different and noteworthy. In a departure from the current trend of pairing leggings with retro white sneakers or sophisticated pointed-toe kitten heels, Teigen opted for heeled black ankle boots. This unconventional choice, reminiscent of its heyday in the 2010s, surprised many, and will no doubt be met with some resistance. Regardless, with Teigen’s unparalleled influence in the world of style, I wouldn’t be surprised if this pairing started popping up in the next year. It’ll be 2014 all over again (minus the infinity scarves).

On that note, keep scrolling to shop the best leggings and ankle boots on the market right now so that you can recreate her fall-ready look in a modern, 2025-ready way.