Scott Disick & Kourtney Kardashian: From Red Carpet Glam to Heartbreak

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The highly anticipated series The Kardashians finally premiered on Hulu in April 2022, drawing fans and curious viewers alike. Yet, not everyone was sold on the new chapter.

Scott Disick arrived with his then-girlfriend Rebecca Donaldson at the star-studded premiere event. Still, sources suggest he may have been less than enthusiastic about diving into the latest Kardashian saga.

Scott’s Reaction to Kourtney and Travis’ Relationship

“Of course, it’s awkward for Scott,” a source told Us Weekly. “He doesn’t take the time to watch the full episodes, and why should he? He doesn’t need to. That’s the last thing he wants to do — relive the awkward moments of him, Travis, and Kourtney. He lived through it already.”

Scott Disick looks relaxed as he spends time with his three children, Mason Disick, Penelope Disick, and Reign Disick, on the beach in MiamiScott Disick looks relaxed as he spends time with his three children, Mason Disick, Penelope Disick, and Reign Disick, on the beach in Miami on February 22, 2022 (Credit: MEGA / WENN)

“He turns away any time he’s around them, and they’re making out,” the source added. “It’s embarrassing and Travis and Kourtney act like no one’s in the room whenever they’re together. Scott’s all about PDA but would never put any of his exes in such an awkward position.”

Scott Disick’s Struggles With Kourtney’s New Life

Scott has repeatedly expressed his discomfort with Kourtney’s new relationship. The new show seems to show affection between the happy couple, apparently more than Disick can stomach.

Scott Disick and his girlfriend Bella Banos walk the beach in St. Barts on December 21, 2021, with Bella stunning in a neon green bikini and Scott keeping it casual in a tropical-print shirt, black swim shorts, and sunglassesScott Disick and his girlfriend Bella Banos walk the beach in St. Barts on December 21, 2021, with Bella stunning in a neon green bikini and Scott keeping it casual in a tropical-print shirt, black swim shorts, and sunglasses (Credit: MEGA / WENN)

Scott and Kendall’s Disagreement Over Invites

Scott was featured in a recent episode in which he and Kendall Jenner disagreed about whether he should still be invited to events.

After being around Scott for about a decade, Kendall wants to support her sister but also values his friendship. So, it doesn’t make much sense when he’s also expressed discomfort around Kourtney and anyone else she has dated.

Kourtney and Scott’s Tumultuous Relationship

Kourtney and Scott had an extensive romance that spanned almost a decade. The couple met in 2006 at the Mexico mansion of Girls Gone Wild creator Joe Francis and hit it off despite Scott being nearly five years younger than Kourtney.

Scott was featured repeatedly in the first Kardashian show, Keeping Up With the Kardashians.

Kourtney Kardashian and Scott Disick step out in coordinated monochrome outfits, with Kourtney looking chic in a flowing black dress, leather jacket, wide-brim hat, and lace-up boots, while Scott keeps it casual in a bomber jacket, gray tee, skinny jeans, and suede Chelsea bootsKourtney Kardashian and Scott Disick step out in coordinated monochrome outfits, with Kourtney looking chic in a flowing black dress, leather jacket, wide-brim hat, and lace-up boots, while Scott keeps it casual in a bomber jacket, gray tee, skinny jeans, and suede Chelsea boots (Credit: Mariotto / INFphoto)

Sometimes, their relationship was, at best, a happy struggle. At one point, Kourtney’s mom had to convince them that getting married wasn’t the best choice for their relationship. Not long after that fiasco, Kourtney caught Scott cheating.

After some time apart, the two returned together and had their first child. This time, Scott struggled with alcoholism. Kourtney was embarrassed by a very public and infamous event involving a restaurant server.

She didn’t want her baby to be exposed to that kind of behavior and called the relationship off once more.

Kourtney Kardashian in a blue crocodile dress and Scott Disick attend the E! 2013 UpfrontKourtney Kardashian in a blue crocodile dress and Scott Disick attend the E! 2013 Upfront at The Grand Ballroom at Manhattan Center on April 22, 2013, in New York City (Credit: ACE / INFphoto)

The relationship continued to bounce between on and off again until 2015. Kourtney and Scott had two more beautiful children together before she called it off for good.

Unfortunately, Scott couldn’t get his alcoholism under control, and he was eventually busted with another woman. Kourtney decided to search for someone who could give her the love she needed and moved on.

Scott Disick and Sofia Richie stroll along the beach in stylish yet contrasting outfits, with Scott in a relaxed black Gucci T-shirt, black shorts, and sunglasses while carrying his white sneakers, while Sofia stuns in a bold red bikini top paired with high-waisted black trousers, accessorized with gold jewelry and round sunglassesScott Disick and Sofia Richie stroll along the beach in stylish yet contrasting outfits, with Scott in a relaxed black Gucci T-shirt, black shorts, and sunglasses while carrying his white sneakers, while Sofia stuns in a bold red bikini top paired with high-waisted black trousers, accessorized with gold jewelry and round sunglasses (Credit: INSTARimages)

Scott has struggled with his relationship with Kourtney and Travis Barker since they got together. They have been trying to co-parent amicably, but he’s jealous of Travis.

Scott may have distanced himself from Kourtney and Travis, but he’s never strayed from his signature luxury streetwear. His effortless style, often featuring suede Chelsea boots and custom-tailored blazers, contrasts with Travis’ grunge-inspired looks.

His comments on their social media posts indicate that he still checks Kourtney’s accounts and dislikes what he sees.

Kourtney and Travis’ Wedding Without Scott

Scott was absent at Kourtney Kardashian and Travis Barker’s Italian wedding. Instead, he chose to have dinner with Rod Stewart, a famous British singer. Afterward, Scott was seen exiting a Hollywood bar at 1 a.m.

Kourtney Kardashian and Travis Barker make a bold fashion statement on the red carpet, with Kourtney in a sleek black cutout jumpsuit featuring sheer gloves and sharp sunglasses, while Travis contrasts in a striking oversized hot pink satin blazer, black outfit, and edgy accessoriesKourtney Kardashian and Travis Barker make a bold fashion statement on the red carpet, with Kourtney in a sleek black cutout jumpsuit featuring sheer gloves and sharp sunglasses, while Travis contrasts in a striking oversized hot pink satin blazer, black outfit, and edgy accessories (Credit: MEGA / WENN)

Since dating Kourtney, Scott has been seen with numerous other women, usually much younger than him. He’s publicly joked about his abysmal romances, as some of his flings have found love shortly after dating him.

Despite their ups and downs, Scott Disick and Kourtney Kardashian have always turned heads with their impeccable fashion choices. Whether attending high-profile events or enjoying casual outings, their style has consistently reflected a mix of sophistication and effortless cool.

As their relationship evolved, so did their fashion, from coordinated red carpet looks to statement footwear moments. One such occasion that perfectly captured their stylish dynamic was Scott’s birthday celebration.

Scott Disick’s Birthday Celebration With Kourtney

Scott Disick exudes effortless sophistication in an all-black ensemble with a sleek blazer, while Kourtney Kardashian stuns in a shimmering black-and-gold mini dress paired with strappy lace-up heelsScott Disick exudes effortless sophistication in an all-black ensemble with a sleek blazer, while Kourtney Kardashian stuns in a shimmering black-and-gold mini dress paired with strappy lace-up heels (Credit: Judy Eddy / WENN)

On May 26, 2015, Scott Disick celebrated his 32nd birthday! He’s four years younger than his girlfriend, Kourtney Kardashian.

The reality TV star began celebrating his birthday at the 1 OAK nightclub in Las Vegas, and his long-time partner was present to celebrate with him…and perhaps to control his drinking as well.

Scott Disick celebrating his 32nd birthday with Kourtney Kardashian at 1 OAK inside the Mirage Hotel and Casino in Las Vegas on May 23, 2015Scott Disick celebrating his 32nd birthday with Kourtney Kardashian at 1 OAK inside the Mirage Hotel and Casino in Las Vegas on May 23, 2015 (Credit: Judy Eddy / WENN)

Stealing the birthday boy’s thunder, the Keeping Up with the Kardashians star flashed her shapely legs and covered up her upper body in a black-and-gold bejeweled mini dress featuring a high neck and long sleeves.

Kourtney Kardashian wears a stud-embellished Balmain dressKourtney Kardashian wears a stud-embellished Balmain dress (Credit: Judy Eddy / WENN)

Allowing her dress to shine, the mom-of-three wore minimal jewelry—just earrings and a few rings.

She let her center-parted dark tresses fall loosely over her shoulders and wore heavy makeup, including lashings of mascara, dark liner, and a glossy pink lip shade.

Kourtney Kardashian flaunts her legs in a black-and-gold studded mini dress for Scott Disick's 32nd birthdayKourtney Kardashian flaunts her legs in a black-and-gold studded mini dress for Scott Disick’s 32nd birthday at 1 Oak in Las Vegas on May 23, 2015 (Credit: Judy Eddy / WENN)

Kourtney wore her favorite Tom Ford sandals for her feet, which feature gold-tone studs, open toes with pointed golden hardware, leather lace-up vamps, 0.5-inch island platforms, and 4.5-inch heels.

Kourtney Kardashian displays her pretty feet in Tom Ford sandalsKourtney Kardashian displays her pretty feet in Tom Ford sandals (Credit: Judy Eddy / WENN)

Stepping Out in Style: The Kardashians in Tom Ford

Tom Ford’s designs have long been a staple in the Kardashian wardrobe, with the sisters frequently showcasing his pieces at various high-profile events. Here are some of their most memorable Tom Ford moments:

Kim Kardashian’s Gold Chain Sandals at the Kardashian Kollection Launch

Khloé Kardashian’s All-White Ensemble with Tom Ford Heels

  • Event: Easter Sunday Church Service
  • Outfit: Khloé stunned in an all-white ensemble featuring an Alaïa cardigan and an embossed A.L.C skirt.
  • Footwear: She added a pop of color with cloud blue suede Tom Ford ankle-lock pumps, featuring a signature padlock detail.
  • More Details: Khloé Kardashian Stuns in All-White With Luxe Tom Ford Heels

Kourtney Kardashian’s Chic Appearance at Kim’s Birthday Bash

  • Event: Kim Kardashian’s 33rd Birthday Party at TAO Nightclub
  • Outfit: Kourtney showcased her style in a black leather skirt with a high slit and a long-sleeved knit top.
  • Footwear: She elevated her look with zebra-print Tom Ford sandals, adding an edgy touch to her outfit.
  • More Details: The Kardashian Sisters Rock Tom Ford at Kim’s Birthday Bash

Unfortunately, Kourtney Kardashian’s sandals by the famous American fashion designer are already sold out.

Tom Ford Lace-Up Platform SandalsTom Ford Lace-Up Platform Sandals, $1,250

Beyond their headline-making relationship, Scott Disick and Kourtney Kardashian have long been recognized for their impeccable style.

Whether attending red carpet events or enjoying casual outings, the former couple consistently showcased their fashion-forward choices.

Scott Disick and Kourtney Kardashian: A Fashion Retrospective

Let’s take a look at some of their most memorable style moments:

Artful Outing in Beverly Hills

  • Event: Visit to RH Contemporary Art
  • Date: November 27, 2015
  • Kourtney’s Outfit: She embraced a chic, casual look with a black-and-white striped lace-up blouse by Faithfull the Brand, black jeans, and Saint Laurent ‘Wyatt’ ankle boots.
  • More Details: Kourtney’s Chic Ensemble During Art Gallery Visit

Casual Lunch in Hollywood

  • Event: Lunch at Il Pastaio
  • Date: December 13, 2016
  • Kourtney’s Outfit: She kept it casual yet stylish in distressed Good American jeans, a black turtleneck, and classic black-and-white Vans ‘Old Skool’ sneakers.
  • More Details: Kourtney’s Effortless Style at Hollywood Lunch

Boho-Chic Maternity Style

  • Event: Outing with Scott Disick in Beverly Hills
  • Date: October 2014
  • Kourtney’s Outfit: While pregnant, she showcased a boho-chic look with a loose-fitting dress and ankle boots, emphasizing comfort without compromising style.
  • More Details: Kourtney’s Boho-Chic Maternity Ensemble

Scott Disick and Kourtney Kardashian may have gone their separate ways, but their fashion influence remains undeniable. From glamorous red carpet moments to effortlessly chic street style, their wardrobe choices have continued to inspire fans worldwide.

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