14 Ways to Wear Cropped Jeans: Celebrity Outfits That Make Your Shoes the Star

Cropped jeans have transitioned from a seasonal trend into a permanent staple of the modern wardrobe.

Defined by a hemline that hits just above the ankle, this silhouette offers the perfect opportunity to showcase footwear, making shoe choice more critical than ever.

Whether you are styling frayed hems in Los Angeles or structured flares in New York City, the key to mastering the look lies in the proportions between the denim and the ankle.

Below, we look back at some of the most influential celebrity outfits that defined the cropped denim movement, offering timeless styling tricks you can apply to your wardrobe today.

1. Emma Roberts Styles Step-Fray Cropped Jeans With Tabitha Simmons “Hermione” Flats

The “Scream Queens” actress seems to be a massive fan of the cropped jeans trend. She has worn these kinds of jeans multiple times.

Emma Roberts pairs Mother “The Insider” crop step-fray jeans with oxblood Tabitha Simmons “Hermione” flats, styling the ankle-baring denim with a leather jacket and a Proenza Schouler Lunch shoulder bag

She rocked the popular Mother “Insider” crop-step-fray jeans in Not Rough Enough for this look.

Emma Roberts showcases Mother “The Insider” crop step-fray jeans with oxblood Tabitha Simmons “Hermione” flats, highlighting how cropped denim naturally spotlights elegant footwear

The American actress paired them with a plain white shirt, Tabitha Simmons’ oxblood “Hermione” flats, a leather jacket from Tory Burch, and a Proenza Schouler leather lunch shoulder bag.

Emma Roberts carries Proenza Schouler’s Lunch leather shoulder bag while entering a building in Midtown, New York City, New York, on April 29, 2016 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

2. Alessandra Ambrosio Keeps It Effortless in Flared Cropped Jeans and Slip-On Shoes

Cropped jeans seem to be perfect for a sunny day out.

Alessandra Ambrosio pairs flared, cropped Mother Denim jeans with a grey knit Feel The Piece sweater and gold Céline aviator sunglasses, finishing the relaxed California street look with minimalist slip-on shoes

Brazil’s favorite Victoria’s Secret model chose to style her flared, ripped Mother Denim jeans with a grey knit Feel The Piece sweater and a pair of slip-on shoes. It can’t get any more comfortable than this.

Alessandra Ambrosio wears flared ripped Mother Denim jeans in Brentwood on February 29, 2016 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

3. Selena Gomez Elevates Cropped Jeans With Manolo Blahnik Pumps and a Mustard Leather Coat

The pop singer gave this pair of jeans extra class and sass by teaming them with a long mustard-yellow leather coat and Manolo Blahnik shoes.

Selena Gomez elevates high-waisted cropped jeans with a mustard-yellow leather trench coat and tan pointed-toe Manolo Blahnik pumps

This just shows how easily cropped jeans can be elevated from casual to classy chic.

Selena Gomez rocked a The Row trench coat and shirt, Vetements denim, and Manolo Blahnik shoes (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

Selena Gomez wears a silver knot Jennifer Fisher choker at the WE Day California held at The Forum in Los Angeles on April 7, 2016 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

4. Kristen Bell Goes Bohemian in Flared Cutoff Jeans and Isabel Marant Gladiator Sandals

Cropped jeans can also be taken on the bohemian route. Kristen wore an embroidered see-through white top paired with flared cutoff jeans while trying to escape the paparazzi by leaving through the back door of a salon in Los Angeles.

Kristen Bell steps out in Los Angeles wearing flared cutoff jeans with an embroidered white lace top, accessorizing with a Saint Laurent tote and Isabel Marant “Jaeryn” eyelet gladiator sandals (Credit: Michael Wright / WENN)

The American actress wore her casual combination with a Saint Laurent bag and Isabel Marant’s “Jaeryn” eyelet mid-heel gladiator leather sandals.

A close-up of Kristen Bell’s feet in Isabel Marant “Jaeryn” eyelet gladiator sandals, featuring studded leather straps and a chunky block heel

5. Lena Headey Dresses Up High-Waisted Cropped Flare Jeans With Red Sandals

The “Game of Thrones” actress gave cropped jeans a more sophisticated look with red sandals and a classic turtleneck sweater. She rocked high-waisted Rachel Comey Legion flared jeans with slant-front pockets and patch pockets at the back.

Lena Headey in sophisticated high-waisted flared jeans at Jimmy Kimmel Live, Los Angeles on January 25, 2016 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

6. Kendall Jenner Masters Summer Street Style With Cropped Flare Jeans and White Sneakers

The television personality worked an effortlessly cool summery look with cropped jeans and a chic ribbed top.

Kendall Jenner in a ribbed crop top and cropped flared jeans as she returns to her car after dining at Nobu Sushi in Malibu on July 16, 2016

Kendall highlighted her broad shoulders and flat abs, wearing a white Are You Am I off-the-shoulder crop top and Re/Done Levi’s high-rise, cropped, flared jeans.

She elevated her chic casual look with a gray scarf tied around her neck, a pair of sunnies, and Kenneth Cole “Kingvel” white sneakers.

7. Kylie Jenner Keeps It Sporty in Raw-Hem Cropped Jeans and Puma Sneakers

Here’s a sexy take on cropped jeans. The television personality wore light-washed, cropped jeans, a white top, and white sneakers for a casual lunch date with her then-boyfriend, Tyga.

Kylie Jenner in casual glam: cropped jeans and white tank during Beverly Hills outing with Tyga on November 8, 2016 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

Her Good American cropped jeans had raw hems and a curvy fit that perfectly showed off her figure. She styled her jeans with a Topshop ribbed cropped cami, flaunting her midriff and cleavage for a sexy, casual look.

To complete her hot-chic outfit, she carried a croc-embossed Hermès bag and wore a pair of white Puma sneakers.

Kylie Jenner in a white crop tank top and raw hem crop jeans (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

We have to hand it to Kylie for pulling off an effortlessly sexy look.

8. Louise Roe Elevates Casual Cropped Jeans With Bold Red Mules

The English presenter made running errands look chic in a pair of straight-cut cutoff jeans.

Louise Roe in cutoff jeans, beige sweater, and red mules (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

She decided to elevate her laid-back jeans with a pair of red mules, which provided a chic contrast to her beige turtleneck sweater. Known for her big feet, Louise also accessorized with a large black tote bag and round sunglasses.

Louise Roe rocks laid-back jeans in West Hollywood on March 2, 2017 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

9. Chanel Iman Brings Cropped Flare Jeans to the Red Carpet With Baby Blue Ankle Boots

Who says jeans are only for the streets? Definitely not the former Victoria’s Secret Angel.

Chanel Iman flaunts her belly button at the W Las Vegas Grand Opening on March 31, 2017 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

In March 2017, Chanel Iman showed up at a Las Vegas event wearing an unconventional red carpet outfit. She rocked a chic pair of mid-rise cropped flare jeans by SJYP Steve J & Yoni P, which feature frayed edges and front slits.

Chanel Iman shows off her midriff in a white cropped blouse and cropped frayed flare jeans (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

Showing off her model flair, she paired her statement jeans with a white cropped blouse with rolled-up sleeves and baby-blue ankle boots with block heels.

10. Leona Lewis Dresses Up Cropped Flare Jeans With Strappy Ankle-Tie Sandals

If you want to elevate your casual cutoff jeans, check out this chic shopping look by Leona Lewis.

Leona Lewis steps out in flared cropped jeans paired with a striped one-shoulder crop top, completing the chic street look with strappy ankle-tie sandals

The British singer added style to her cropped flare jeans with a gold buckled belt, a one-shoulder ruffled crop top, and a pair of strappy ankle-tie sandals.

Leona Lewis shopping at Planet Blue in Beverly Hills on August 15, 2017 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

She also styled the look with a black bag and a selection of delicate gold jewelry.

11. Bella Hadid Turns Heads in Patchwork Cropped Jeans and Stuart Weitzman Booties

High-waisted jeans and crop tops are a match made in fashion heaven.

Bella Hadid steps out of her hotel during Milan Fashion Week Spring/Summer 2018 on September 23, 2017 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

2016 Model of the Year Bella Hadid dared to reveal more skin than usual in her Esteban Cortazar twist-front crop sweater, paired with high-waisted patchwork cutoff jeans.

Bella Hadid pairs patchwork cropped jeans with a red twist-front crop sweater, completing the bold street-style look with sleek black ankle boots

She added a trendy black Alexander Wang fanny pack to her look, along with a pair of Roberi & Fraud sunglasses and a pair of Stuart Weitzman black booties. This is, without a doubt, a head-turning look.

12. Karlie Kloss Channels Monochrome Cool With Cropped Jeans and Christian Louboutin Flats

The Project Runway host curated an interesting airport look, wearing a pair of black skinny, cropped jeans.

Karlie Kloss channels Michael Jackson in black skinny cropped jeans styled with a white tee, a leather biker jacket, and Christian Louboutin “Montezumo Donna” flats

Channeling the late King of Pop, Michael Jackson, Karlie Kloss teamed her J Brand jeans with monochrome black-and-white pieces.

Her outfit included a white tee by Hanes x Karla, a black leather jacket by Breaking Hearts and Burning Rubber, and a pair of “Montezumo Donna” flats by Christian Louboutin.

Karlie Kloss rocks Christian Louboutin’s Montezumo Donna flats at Los Angeles International Airport (LAX) on December 6, 2017 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

She completed her look with a pair of white ankle socks and black Saint Laurent sunnies.

13. Gigi Hadid Styles Raw-Hem Cropped Jeans With Tabitha Simmons Leopard Boots

The Dutch/Arab supermodel nailed daytime street style in straight-cut jeans with a raw hemline. She styled them with a Vince cashmere pullover worn underneath a Maje x Schott sheepskin jacket in the same butterscotch color.

Gigi Hadid pairs cropped straight-leg jeans with a camel sweater and quilted bomber jacket, finishing the layered street look with Tabitha Simmons “Gigi” leopard-print ankle boots

She then complemented her outfit with animal print Tabitha Simmons “Gigi” ankle boots, black tights, Linda Farrow sunglasses, and a studded Valentino bag.

Gigi Hadid rocks Tabitha Simmons Gigi ankle boots while leaving her apartment in Manhattan on March 19, 2018 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

14. Lucy Hale Makes Errands Chic in Vintage Cropped Jeans and White Booties

The Pretty Little Liars star turned running errands into a head-turning fashion moment. Picking up her dog from doggie daycare, Lucy opted to wear a pair of chic high-rise vintage crop jeans.

Lucy Hale turns errand-running into a fashion moment in high-rise vintage crop jeans while picking up her dog in Los Angeles on January 5, 2019 (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

She simply teamed them with a white crop top and added a furry coat and a pair of white booties, which amp up her casual day look.

Lucy Hale wears a pair of vintage crop jeans with a white tee, coat, and white boots (Credit: TNYF / WENN / Charlie Steffens / Michael Wright)

More Celebrity Outfit Ideas That Prove Cropped Jeans Always Work

From pointed-toe pumps and ankle boots to platform sandals and laid-back sneakers, these celebrity outfits show just how versatile cropped jeans can be across seasons, settings, and personal styles. For more inspiration on how stars style ankle-baring denim with standout shoes, explore these related Your Next Shoes features below.