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.
Shop the best leggings and ankle boots
J.Crew
New Stevie Ankle Boots in Leather
H&M
Cotton Jersey Leggings
These leggings are priced under $10, making them the perfect choice to buy multiples of.
Madewell
The Dimes Kitten Heel Boots
“I love love love these boots,” says a happy Nordstrom customer.
Splits59
Airweight 7/8 Leggings
The leggings are incredibly lightweight, making it feel like you’re not wearing anything at all.
The wide-ankle design really flatters the leg.
Marc Fisher LTD
Kolton Kitten Heel Bootie
Marc Fisher creates stylish, high-quality boots for budget-conscious shoppers.
Wolford
Perfect Fit Leggings
They’re called the “Perfect Fit Leggings” for a reason.
Dolce Vita
Azalea Pointed Toe Bootie
The sock-like ankle design seamlessly pairs with leggings.
Fashion people everywhere rave about these leggings.
These are on my fall wish list.
Strut-This
The Luca Ankle Legging
The color block design really elevates the look of these.
AEYDE
Neil Leather Chelsea Boots
The low block heels makes these comfortable for everyday wear.
Norma Kamali
Legging With Footie
The stirrup detail will help keep your leggings tucked into your boots.
KHAITE
Nevada Leather Ankle Boots