Fashion-Face Off: Ariana Grande vs. Kylie Jenner

Published on September 13, 2019. Updated December 1, 2022

When it comes to style, Ariana Grande and Kylie Jenner are some of the world’s most influential icons. While Ariana’s style is sweet, flirty and filled with oversized pieces, Kylie’s style is more simple with many sheer and bodycon dresses. It’s clear their style differs quite a bit, but that’s not to say they haven’t had a moment or two where they’ve dressed similarly, especially in their younger years. Follow along for our ultimate Ariana Grande and Kylie Jenner fashion faceoff and be sure to vote on which look is your favorite!

Want exclusive celebrity fashion content delivered straight to your inbox? Sign up for our newsletter and get all of the latest celebrity fashion news, red carpet pics, fashion face-offs and more!

20. The Two-Piece Black Look

A simple two-piece set can work for multiple occasions, which is clear by both Ariana and Kylie’s looks here! While Ariana opted for a sparkling two-piece set with translucent detailing on the skirt while on tour, Kylie Jenner opted for a more tame version of this look while attending an event. Whose black two-piece look do you like better — Ariana’s concert look or Kylie’s event look?

Photo by Jamie McCarthy/Getty Images for Mercedes-Benz | Photo by Larry Busacca/Getty Images

19. The Oversized Shirt Dress

Oversized shirts and sweaters are a classic Ariana Grande look in recent years, but Kylie’s definitely a huge fan of the trend as well! Whose oversized shirt dress do you like better? Ariana’s grey sweater and over-the-knee boot combo or Kylie Jenner’s oversized white tee paired with bright purple boots? Be sure to vote below!

Photo by Kevin Mazur/Getty Images for March For Our Lives

18. The White Skater Dress

Skater skirts and dresses were a huge trend around the time Ariana and Kylie’s careers began taking off. They both wore similar lace dresses on different occasions during these years! Ariana stepped out at the MTV Movie Awards wearing a white dress that was covered in pink beading and lace at the top. Kylie wore a similar look but hers was cinched at the waist with a metallic silver belt. Whose look do you prefer?

Photo by Jason Merritt/Getty Images | Shutterstock

17. The Pastel Coat

Pastel-colored coats are a popular trend among many celebrities, Ariana Grande and Kylie Jenner included! While Ariana favored a light lavender coat which she paired on top of a black jumpsuit, Kylie wore a cape-style blush pink coat with white lapels. Whose pastel coat look do you like better?

Photo by Stuart C. Wilson/Getty Images | Photo by Craig Barritt/Getty Images

16. The Purple Ruffled Look

Despite their differing styles, it’s clear that both Ariana and Kylie won’t hesitate to put on a girly purple dress with ruffles! While Ariana’s look is a structured lavender minidress that she paired with over-the-knee boots, Kylie’s is a darker shade of purple with cutouts and dramatic ruffles. Whose look do you prefer?

Press Association

15. The Metallic Minidress

Both Ariana and Kylie are huge fans of metallics! While Ariana is photographed here at an early appearance in her career for the premiere of Twilight wearing a beaded silver dress, Kylie is photographed attending a fashion show in New York wearing a fringe silver number. Whose metallic minidress do you prefer?

Michael Germana/Everett Collection | Kristin Callahan/Everett Collection

14. The Olive Cargo Look

Both Ariana and Kylie are fans of olive green and we’re not surprised since the shade is so complementary to their dark features! While Ariana opted to wear olive green cargo pants while performing, Kylie wore a casual strapless jumpsuit in the shade paired with bright purple stilettos. Whose olive cargo look do you prefer?

Photo by Kevin Mazur/Getty Images | Photo by Kevin Mazur/Getty Images

13. The Electric Blue Look

During their younger years, both Ariana Grande and Kylie Jenner were huge fans of bright electric blue! While Ariana opted for a blue and black cutout look for the Billboard Music Awards, Kylie opted for a layered chiffon shift dress for an event of her own. Whose blue look do you prefer?

EPA/NINA PROMMER | Photo by Frazer Harrison/Getty Images

12. The Sheer Skirt Look

Sheer skirts were a huge trend a few years back, and both Ariana Grande and Kylie Jenner were fans! While Ariana opted for a feminine pink sheer look with cutouts on the bodice, Kylie opted for a darker look with a black sheer dress that was belted at the waist. Whose sheer skirt look do you prefer?

Source: Shutterstock

11. The Beaded Look

In the past, Ariana and Kylie have worn remarkably similar beaded ensembles! While the then-redheaded Ariana opted for a beaded romper that belted at the waist, Kylie opted for a beaded suit which she paired with a crop top. Whose beaded look do you prefer?

10. The White Minidress

Every girl needs a good white minidress in her wardrobe, and clearly, this is a philosophy both Ariana and Kylie stand behind! While Ariana opted for a white textured minidress and wore her hair in a half-ponytail, Kylie opted for a cap sleeve dress with her hair long and straight. Whose ensemble do you prefer?

Photo by Jason Merritt/Getty Images | Shutterstock

9. The Pink Structured Look

Both Ariana and Kylie aren’t afraid to step outside the box when it comes to fashion, which is clear by both of these pink structured outfits! While Ariana opted for a black and white beaded look with a pink ruffle detail, Kylie wore a pink suit with a structured halter bodice. Do you like Ariana or Kylie’s look better?

8. The Monochrome Number

You can never go wrong with black and white! While Ariana opted for a ’60s-inspired mod minidress while performing, Kylie opted for a long sleeve black and white number with a cutout. Whose monochrome number do you prefer?

Photo by Ethan Miller/Getty Images | Photo by Vivien Killilea/Getty Images for Rodial

7. The Burgundy Dress

When it comes to glitzy event looks, both Ariana and Kylie love burgundy! While Ariana Grande opted for a floor-length sequin gown for the American Music Awards, Kylie Jenner opted for a body-hugging satin number with a slit. Whose burgundy dress do you prefer?

6. The Black Two-Piece Look

Black is a beloved fashion color of both Ariana and Kylie, especially when an interesting detail like cutouts or a two-piece set is involved. While Ariana opted for a black look with a lace crop top and trousers, Kylie wore a black strapless dress with a cutout along the bodice. Whose look do you prefer?

Press Association | Photo by Lionel Hahn/ABACAPRESS.COM

5. The Red Floor-Length Number

Nothing says glamour like a floor-sweeping red dress! For the Grammy Awards, Ariana opted for a long red dress with a corset bodice. Kylie wore a similar dress while backstage at the Heart Truth 2013 Fashion Show but hers had a simple high neckline. Whose red floor-length number do you prefer? Ariana’s corset look or Kylie’s simple gown?

Photo by Broadimage/REX/Shutterstock | Theo Wargo/Getty Images for Heart Truth

4. The Cutout Dress

While their styles may greatly differ, both Ariana and Kylie share a mutual love of cutouts! While Ariana wore this black number with cutouts along the bodice and chest, Kylie wore a high-neck black number that hugged her curves and showed some skin around the hips. Whose cutout look do you prefer?

Photo by Ian Gavan/Getty Images for MTV | Photo by Mike Windle/Getty Images for GQ Magazine

3. The White & Silver Look

When it comes to events, both Ariana and Kylie love a simple white dress! For the Grammy Awards in 2015, Ariana opted for a sleek white number with silver sequin detailing on one side. Kylie wore a white and silver look of her own while attending the 2015 NBCUniversal Cable Entertainment Upfront. Kylie’s look featured long sleeves and a thick silver belt. Whose look do you prefer?

Photo by Broadimage/REX | Photo by Donna Ward/Getty Images

2. The Tangerine Dress

Tangerine is the perfect eye-catching summer color and both Ariana and Kylie have worn it in the past! While Ariana opted for a simple high-neck orange dress which she paired with a bedazzled clutch, Kylie opted for an asymmetrical wrap style dress which she paired with strappy sandals. Which orange dress do you prefer?

Press Association | Photo by Araya Diaz/Getty Images

1. The Leather Look

Ariana and Kylie definitely aren’t shy to rock a full leather dress! While Ariana wore a leather minidress with gold zippers and over-the-knee boots, Kylie opted for a leather cutout number with silver beading and embellishment. Whose leather look do you prefer? Ariana’s or Kylie’s?

Dee Cercone/Everett Collection | Press Association