Kourtney Kardashian has always been the sister with the funniest one-liners in the Kardashian-Jenner clan, but when it comes to fashion, she historically was viewed as the one who played it safer than, say, Kim Kardashian. But recently, Kourtney Kardashian’s style aesthetic has completely transformed. Since dating and marrying Blink-182 drummer, Travis Barker, the eldest sister has adopted a new fashion point-of-view, one that borrows from the edgier 2000s fashion trends to great effect.
In January of 2023, she delivered a literal spin on the naked dress in a Balmain gown bearing a nude Renaissance painting. She kept the dark, alluring vibes going with her wedding wardrobe, first tying the knot in Vegas wearing matching leather jackets. When she later hosted her wedding weekend in Italy, her looks ranged from sheer gowns to corsed minidresses. Her wedding minidress was considered a major style statement, as most brides opt for a longer gown to walk down the aisle. Kardashian, however, broke the sartorial mold in a bridal corset minidress with sheer lace panels on both hips.
The Lemme mogul, 44, continued to push the envelope when she announced her pregnancy at a Blink-182 concert on June 16. Wearing a sheer bodysuit with low-rise pants that gave the illusion of hip cutouts, Kourtney Kardashian’s style evolution was on full display. Her sharp-angled bob, visible bra, and glazed-doughnut manicure added plenty of personality.
Scroll on for a closer look at some of Kourtney Kardashian’s best style moments of all time.
Related: 20 Kourtney Kardashian and Travis Barker Looks That Prove They’re Always in Sync
Getty Images / John Shearer
Kourtney Kardashian at the Met Gala, May 2022
Kourtney Kardashian wearing a Thom Browne white cropped top and high-waisted colorblock skirt at the Met Gala on May 2, 2022.
Getty Images / Jason Kempin
Kourtney Kardashian at the VMAs, September 2021
Kourtney Kardashian wearing a black minidress with a lace up front cutout at the VMAs on September 12, 2021.
Getty Images / Pierre Suu
Kourtney Kardashian at Paris Fashion Week, March 2020
Kourtney Kardashian wearing a brown latex catsuit and black sunglasses at Paris Fashion Week on March 1, 2020.
NBCU Photo Bank via Getty Images / Christopher Polk/E! Entertainmen
Kourtney Kardashian at the People's Choice Awards, November 2019
Kourtney Kardashian wearing a black, glitter pinstripe suit at the People’s Choice Awards on November 10, 2019.
Getty Images for GQ / Stefanie Keenan
Kourtney Kardashian at "GQ"'s Men of the Year Party, December 2018
Kourtney Kardashian wearing a silver strapless dress at “GQ”‘s Men of the Year Party on December 6, 2018.
WireImage / Tommaso Boddi
Kourtney Kardashian at the alice + olivia Show, April 2016
Kourtney Kardashian wearing a suede dress, choker, and matching heels at the alice + olivia show on April 13, 2016.
Dave Benett/Getty Images / David M. Benett
Kourtney Kardashian at the Glamour Women of the Year Awards, June 2016
Kourtney Kardashian wearing a burgundy dress with a plunging neckline at the Glamour Women of the Year Awards on June 7, 2016.
GC Images / John Parra
Kourtney Kardashian in Miami, July 2016
Kourtney Kardashian wearing a studded one-shouldered swimsuit in Miami on June 4, 2016.
GC Images / Raymond Hall
Kourtney Kardashian at "The Today Show," April 2016
Kourtney Kardashian wearing a green t-shirt tucked into a leather skirt outside “The Today Show” on April 12, 2016.
WireImage / John Lamparski
Kourtney Kardashian at the Angel Ball, November 2016
Kourtney Kardashian wearing a strapless ballgown with sheer panels at the Angel Ball on November 21, 2016.
GC Images / Steven Gonzalez
Kourtney Kardashian on Miami Beach, September 2016
Kourtney Kardashian wearing a coral-hued one piece suit on Miami Beach on September 17, 2016.
GC Images / BG003/Bauer-Griffin
Kourtney Kardashian in Los Angeles, June 2016
Kourtney Kardashian wearing a striped off-the-shoulder top and white jeans in Los Angeles on June 7, 2016.
GC Images / Marc Piasecki
Kourtney Kardashian in Paris, September 2016
Kourtney Kardashian wearing a crop top and high-waisted jeans in Paris on September 30, 2016.
GC Images / J. Almasi
Kourtney Kardashian at Cannes Film Festival, May 2017
Kourtney Kardashian wearing an off-shoulder white dress and dangling gold earrings at Cannes Film Festival on May 23, 2017.
GC Images / J. Almasi
Kourtney Kardashian at Cannes Film Festival, May 2017
Kourtney Kardashian wearing a red one-piece suit at Cannes Film Festival on May 22, 2017.
GC Images / Robino Salvatore
Kourtney Kardashian at Cannes Film Festival, May 2017
Kourtney Kardashian wearing a white bralette and flowing pants at Cannes Film Festival on May 24, 2017.
GC Images / BG001/Bauer-Griffin
Kourtney Kardashian in Los Angeles, April 2017
Kourtney Kardashian wearing a band T-shirt, distressed jeans, and aviator sunglasses in Los Angeles on April 5, 2017.
Dave Benett/Getty Images / David M Benett
Kourtney Kardashian at "Wonders Of The Sea" Dinner, May 2017
Kourtney Kardashian wearing a sequin minidress at “Wonders Of The Sea” dinner on May 21, 2017.
GC Images / Gustavo Caballero
Kourtney Kardashian in Miami, April 2016
Kourtney Kardashian wearing a sheer lace dress in Miami on April 23, 2016.
WireImage / JB Lacroix
Kourtney Kardashian at "The Promise" Premiere, April 2017
Kourtney Kardashian wearing a classic pantsuit at “The Promise” premiere on April 12, 2017.
GC Images / John Parra
Kourtney Kardashian in Miami, September 2016
Kourtney Kardashian wearing a minidress and thigh-high boots in Miami on September 15, 2016.
GC Images / Marc Piasecki
Kourtney Kardashian at Paris Fashion Week, October 2016
Kourtney Kardashian wearing a black cutout dress at Paris Fashion Week on October 2, 2016.
GC Images / Hollywood To You/Star Max
Kourtney Kardashian in Los Angeles, March 2017
Kourtney Kardashian wearing a black lace dress, leather jacket, and PVC-strap heels in Los Angeles on March 30, 2017.
Getty Images for Amazon's Style / John Sciulli
Kourtney Kardashian on "Amazon's Style Code Live," November 2016
Kourtney Kardashian wearing a beige long-sleeved shirt and leather trousers on “Amazon’s Style Code Live” on November 4, 2016.
WireImage / Steve Granitz
Kourtney Kardashian at a Pre-Grammy Gala, February 2017
Kourtney Kardashian wearing a black cutout, high-slit gown at a Pre-Grammy gala on February 11, 2017.
