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25+ Kardashian Family Wardrobe Moments That Made Headlines

Fashion is a captivating world filled with glitz, glamor, and occasionally, some serious missteps. Enter the Kardashian-Jenner clan, renowned for their trendsetting prowess and enviable style. Yet, even these fashion icons have had their fair share of questionable moments that left heads turning for all the wrong reasons. From red carpet catastrophes to daring ensembles

Fashion is a captivating world filled with glitz, glamor, and occasionally, some serious missteps. Enter the Kardashian-Jenner clan, renowned for their trendsetting prowess and enviable style. Yet, even these fashion icons have had their fair share of questionable moments that left heads turning for all the wrong reasons.

From red carpet catastrophes to daring ensembles that missed the mark, we’re delving into the memorable Kardashian fashion fails that have sparked debates and raised eyebrows in equal measure. Despite their status as fashion mavens, these instances serve as a reminder that even the most celebrated wardrobes can sometimes miss the mark.

1. Kim’s Diaper Jumpsuit

Year: 2022
Est. Cost of Outfit: $500-1,000*

Kim Kardashian made a bold fashion statement at Milan Fashion Week Fall-Winter 2022-2023 with her choice of an eye-catching orange jumpsuit. The outfit sparked discussions among fashion enthusiasts, drawing attention to its striking hue and sleek silhouette.

While the designer remained a mystery, the jumpsuit’s appeal lay in its ability to blend high-end couture with budget-friendly chic. Whether a thrift store find or a custom creation, Kim effortlessly commanded attention, proving that confidence and charisma trumped price tags when it came to style!

2. Kylie’s Questionable Lion Head

Year: 2023
Est. Cost of Outfit: $6,000-19,000*

Kylie Jenner turned heads at Paris Fashion Week 2023 with her daring lion head accessory, sparking both awe and amusement among fashionistas. The quirky choice raised eyebrows and prompted lively discussions about its origins and significance.

Whether a stroke of genius or a whimsical impulse buy, the accessory’s boldness embodied Kylie’s fearless approach to fashion. In a world where conformity often reigned, her willingness to take risks served as a reminder that true style was about embracing individuality with a touch of wit. After all, in the jungle of fashion, it was the ones who dared to roar that truly stood out!

3. Kourtney’s Hippie Outfit

Year: 2015
Est. Cost of Outfit: $600-900*

Kourtney Kardashian made waves in St. Barts back in 2015 with her choice of a mesmerizing frilly white dress, enchanting onlookers with its breezy elegance. The ensemble garnered admiration and fascination, with fashion aficionados lauding its intricate design and effortless sophistication.

While the designer of the dress remained undisclosed, its timeless allure spoke volumes about Kourtney’s innate sense of style and flair. Whether a vintage gem or a bespoke creation, she effortlessly radiated confidence, proving that true fashion prowess transcended mere price tags. After all, in the realm of style, it was the allure and grace of the wearer that truly captivated!

4. Kim’s Oatmeal Muffin Dress

Year: 2013
Est. Cost of Outfit: $3,500*

Kim Kardashian’s fashion journey encountered a hiccup in New York City on March 26, 2013, as she showcased her baby bump in a number that resembled a freshly baked oatmeal muffin. Despite her usual flair for bold choices, this particular ensemble missed the mark, evoking mixed reactions and raising eyebrows within the fashion circles. The distinctive silhouette of the dress, though aiming for maternity chic, inadvertently became a symbol of a fashion misstep.

With an estimated outfit cost of $3,500, the dress served as a reminder that even with a significant price tag, experimentation didn’t always guarantee success in the ever-evolving landscape of celebrity style.

5. Kendall’s Crocheted Sweater

Year: 2017
Est. Cost of Outfit: $3,000-10,000*

Kendall Jenner strutted into the limelight at London Fashion Week 2017, rocking an oversized crocheted sweater that had tongues wagging and fashionistas giggling. Whether a bold fashion gambit or an accidental comedy goldmine, the sweater’s unexpected charm encapsulated Kendall’s cheeky style.

In an industry often draped in seriousness, her knack for injecting humor into her fashion choices was a sassy reminder that true style is not just about looking good but also having a little fun with your wardrobe. After all, in the wild world of fashion, it was those who made you smirk that truly stole the show!

6. Kim’s Rhinestone Cowgirl Look

Year: 2015
Est. Cost of Outfit: $5,000- 15,000*

Kim Kardashian’s studded fringe number crashed the style party at the Balmain extravaganza during Paris Fashion Week on March 5, 2015. This audacious ensemble, blending studded glam with fringe fabulousness, had fashionistas wide-eyed and ready for a spectacle. Whether a calculated triumph, an accidental trendsetter, or a cheeky rhinestone cowgirl fashion fail, Kim’s fringe number flaunted Parisian couture with a wink.

In a realm often draped in predictable elegance, this ensemble stood as a sassy reminder that true style is about throwing caution to the wind and embracing the unexpected. After all, in the glittering chaos of Paris Fashion Week, it was the ones who made heads spin that truly stole the spotlight!

7. Khloé’s Silver Christmas Pantsuit

Year: 2017
Est. Cost of Outfit: $5,000-15,000*

Khloé Kardashian’s Silver Christmas Pantsuit in 2017 sparked lively discussions as she proudly displayed her baby bump in a custom silver fringed Yousef Al Jasmi jumpsuit paired with a chic fur coat. The festive attire prompted playful banter—was Khloé channeling an ice queen or Glenda the Witch of the North?

The cheeky comment about tinsel belonging on Christmas trees cleverly suggested the unconventional mix-up in Khloé’s outfit. Despite the fashion banter, Khloé’s bold choice added glamor to the holiday, proving that even a tinsel-topped ensemble could become a memorable part of the festive season.

8. Kim’s Floral Fashion Faux Pas

Year: 2013
Est. Cost of Outfit: $5,000-15,000*

Kim Kardashian’s Givenchy dress at the 2013 Met Gala turned heads for all the wrong reasons, marking a floral fashion faux pas. Going beyond floral overload, she added an unexpected twist—matching gloves and a turtleneck. The ensemble stirred mixed reactions, with some applauding the boldness, while others raised eyebrows at the unconventional combination.

Kim’s daring fashion choice at the prestigious event showcased that in haute couture, experimenting with style can either be a hit or a miss. In this case, it certainly created a floral storm of opinions.

9. Kim’s Blackout Attire

Year: 2021
Est. Cost of Outfit: Undisclosed

Was it a dementor making a chic cameo in the wizarding world, or was it just Kim Kardashian slaying at the 2021 Met Gala? Rocking a black Balenciaga bodysuit, she channeled an enigmatic vibe, giving off serious dementor elegance. Wrapped head to toe in black, with only a ponytail peeking out, Kim blurred the line between fantasy and high fashion.

A true show-stopper, her daring choice not only challenged the norms of red carpet attire but also showcased her fearless fashion approach. The outfit left onlookers questioning if they were witnessing a magical creature or a celeb weaving her spell on the red carpet – another day in Kim’s glam sorcery!

10. Kourtney’s Black Veil Mini

Year: 2022
Est. Cost of Outfit: Undisclosed

Kourtney Kardashian and Travis Barker’s pre-wedding Italian yacht lunch in 2022 intrigued as Kourtney flaunted another Dolce & Gabbana creation — a black mini dress with a matching veil. The ensemble stirred speculation, leaving attendees questioning whether it was a wedding or a funeral. Despite the ambiguity, the daring fashion choice injected drama into the pre-wedding festivities, boldly showcasing Kourtney’s fearless style.

Ironically, the unconventional outfit, with its funeral-like somber tones, might just have been the perfect attire for a yacht ride … sarcasm intended. The striking black against the scenic Italian backdrop ensured Kourtney’s bold statement lingered in conversations well beyond the lunch event.

11. Kendall’s Sequined Long Sleeved Bodysuit

Year: 2023
Est. Cost of Outfit: Undisclosed

Kendall Jenner’s 2023 Met Gala appearance exuded superhero chic with a pantsless ensemble, bedazzled oversized collar, and capes on both arms. The daring fusion of Austin Powers’ retro charm and comic book superhero aesthetics showcased Kendall’s avant-garde style, turning the red carpet into a whimsical runway.

While some admired her fearless approach, critics found the eccentric combination a departure from the Gala’s traditional elegance. Nevertheless, the bejeweled collar and superhero capes undeniably created a captivating visual spectacle, cementing Kendall’s reputation as a trendsetter who fearlessly redefined fashion norms on the prestigious Met Gala stage.

12. Kim’s Flame Dress (with fuzzy Glasses)

Year: 2022
Est. Cost of Outfit: Undisclosed

Kim Kardashian’s 2022 LA look turned heads, but not necessarily for the right reasons. Donning fuzzy glasses and a turtleneck in scorching temperatures prompted scrutiny of her fashion choices. The introduction of red leather added fuel to the fire, creating an attention-grabbing ensemble that made observers question if she had been burning up both outside and inside.

Whether an intentional style statement or an inadvertent heatwave, Kim’s sizzling appearance sparked debates about the delicate balance between fashion and comfort in the city of angels. The enigmatic inclusion of fuzzy glasses left lingering questions, emphasizing the blurred line between daring fashion and practicality.

13. Kylie’s Denim Tube

Year: 2022
Est. Cost of Outfit: Undisclosed

Kylie Jenner was a walking keychain, complete with a choker and denim boots to match, as she strutted into Sun Studios in London in 2022. It seemed like she might have raided the hardware store for her ensemble, donning a strapless denim dress that added a touch of industrial chic to her look.

With the metal accents resembling key rings, Kylie’s fashion statement turned heads and raised questions about whether she found inspiration in unexpected places. This daring choice transformed everyday elements into a bold and unique fashion narrative, showcasing Kylie’s ability to turn heads and redefine conventional style norms.

14. Kendall’s Pink Tulle Princess Gown

Year: 2019
Est. Cost of Outfit: Undisclosed

Kendall Jenner stole the spotlight at the Cannes amfAR Gala in 2019, donning a show-stopping hot pink Giambattista Valli dress. The cotton candy, bubblegum princess gown was a fuchsia explosion, prompting a delightful debate on whether it was too much or the perfect Barbie getup.

Kendall’s audacious choice not only commanded attention but served as a whimsical reminder that in the world of high fashion, embracing bold colors and extravagant styles was an art form. The Cannes red carpet transformed into a vibrant canvas as Kendall effortlessly straddled the line between fashion extravaganza and playful elegance.

15. Kim’s Head to Toe Black Sequins

Year: 2022
Est. Cost of Outfit: $5,000-15,000*

Kim Kardashian confidently slinked into her “modern Catwoman” ensemble, decked in head-to-toe black sequins, a salute to her nine fashion lives. The black Balenciaga gown, paired with a matching ski mask, turned an ordinary day at the office into a high-stakes fashion heist.

Kim’s daring escapade into Catwoman glam wasn’t just an outfit; it was a statement – each appearance was a chapter in her stylish saga. With sequins that shimmered like well-kept secrets and a ski mask signaling readiness for a fashionable caper, Kim’s look was a witty twist on the mundane. Taking a cheeky break from thwarting fashion crimes, she posed on her couch in a stylish vigilante in repose.

16. Khloé’s “Mummy” Mini

Year: 2023
Est. Cost of Outfit: $800-$1000*

Khloé Kardashian embraced “mummy” chic in 2023 with the Alexander Wang one-shoulder ruched jersey mini dress, but instead of the dramatic scenes from “The Mummy” with Brendan Fraser, it was a fashion fail straight out of “The Kardashians” season four.

Stepping into the tomb of trends, Khloé turned a one-shoulder mini dress into a headline-worthy moment, blurring the line between couture and reality TV. With each ruched detail and every on-screen misstep, this ensemble became a testament to Khloé’s bold style choices — even if it occasionally resulted in a fashion fail that kept fans talking.

17. Kendall’s Giant Scrunchie Dress

Year: 2024
Est. Cost of Outfit: $8,000-10,000*

Kendall Jenner floated on the runway at the Jacquemus Spring 2024 Show, wrapped in a white cloud-like minidress that was part marshmallow dream, part giant’s scrunchie fantasy. The Palace of Versailles became a playground for Kendall’s whimsical fashion escapade.

Was it haute couture or an accessory for a fashion-forward giant? The dress triggered a playful debate, leaving spectators wondering if they were witnessing a runway show or a whimsical chapter from a giant’s fashion diary. Kendall, as always, blurred the lines between fashion and fantasy, turning the catwalk into her very own magical storybook.

18. Kourtney’s Maroon Misstep

Year: 2022
Est. Cost of Outfit: Undisclosed

In Portofino 2022, Kourtney Kardashian donned a red corset dress with a sheer bottom, which was a daring departure. The maroon hue, while attention-grabbing, slightly clashed with the coastal charm. The sheer bottom added a playful touch, though it might have been seen as a risk not fully realized.

Despite this, Kourtney’s fearless experimentation with fashion deserved applause, showcasing her willingness to push boundaries. While the ensemble might not have been everyone’s cup of tea, it sparked intriguing discussions, proving that personal style was a dynamic journey open to interpretation.

19. Kim’s Wild Catsuit

Year: 2022
Est. Cost of Outfit: $5,000-15,000*

Kim Kardashian stunned at Milan Fashion Week in a head-to-toe leopard-print ensemble by Dolce & Gabbana. The bold choice raised questions: was it too wild or just the right dose of fashion drama for Kim? As a style icon, she navigated the fine line between audacious and chic effortlessly.

The all-encompassing leopard print might have prompted inquiries about pushing the boundaries, but for Kim, it was a statement. The real question emerged: could anyone wear too much leopard? Kim’s fearless fashion journey suggested that, when done with confidence, there was always room for more spots in the spotlight.

20. Kourtney’s Hot-Toe Heels

Year: 2015
Est. Cost of Outfit: $100- 500*

Kourtney Kardashian’s hot-toe heels, fashioned after a foot sauna, evolve into a cringe-worthy fashion fail. The embarrassing misstep leaves Kourtney’s toes metaphorically gasping for CPR, serving as a live-and-learn moment, highlighting the importance of allowing even trendy jellies ample room to breathe.

Although the rest of her outfit may exude elegance, the moral is evident: simply avert your gaze from her feet. This serves as a humorous lesson in the dangers of prioritizing fashion over comfort, demonstrating that even the most stylish choices can encounter unforeseen pitfalls.

21. Kendall’s Leather Glove, Green Frock Ensemble

Year: 2023
Est. Cost of Outfit: $8,000-20,000*

Kendall Jenner’s leather glove and green frock ensemble showcased a daring choice in Dubai 2023. Donning a dress and gloves from the Victoria Beckham Collection, Kendall’s ensemble made a bold truce with chartreuse. The mix, although not so posh and slightly missing the spice, delivered a unique fashion statement.

This unconventional pairing in the luxurious setting of Dubai added a touch of avant-garde flair, proving that sometimes, a departure from the conventional could create a memorable and conversation-worthy style moment.

22. Kim’s Caramel Candy Apple Romper

Year: 2020
Est. Cost of Outfit: $10,000-15,000*

Kim Kardashian’s caramel candy apple romper, showcased during Paris Fashion Week, was a daring choice that raised eyebrows. The latex suit, resembling a caramel candy apple, leaned more towards a comfort fail than a fashion statement.

The outfit’s unconventional design prompted questions about its practicality, and it seemed more suited for a carnival snack than a high-fashion event. Kim’s bold fashion choices often pushed boundaries, and this one, while not necessarily a fashion fail, certainly challenged traditional notions of comfort and style.

23. Kim’s Mop Dress

Year: 2013
Est. Cost of Outfit: Undisclosed

Kim Kardashian at the Louise Goldin Fashion Show in 2013 donned the infamous mop dress, sparking varied reactions. Was Kim there to clean up the house, was it a fashion fail, or did it prove she could look good in literally anything under the kitchen sink?

The mop dress, with its unconventional design, blurred the lines between avant-garde fashion and household utility. Whether a bold statement or an unintentional mishap, Kim’s willingness to experiment showcased her versatility and ability to turn heads, even in the most unconventional ensembles.

24. Kendall’s Green Martian Look

Year: 2020
Est. Cost of Outfit: $700-15,000*

Kendall Jenner’s green martian look at the 2020 Brit Awards after-party was a celestial spectacle, akin to space frog glam. Bedecked in neon green, Kendall channeled an extraterrestrial aura with bold highlighter hues.

The avant-garde ensemble blurred the line between futuristic and fashionable, turning heads and sparking conversations. The Brit Awards after-party became a cosmic runway for Kendall, showcasing her ability to transcend conventional style and create memorable, out-of-this-world fashion moments. Was this a fail-ian invasion of the final fashion frontier?

25. Kris’s Loud Yellow Suit

Year: 2018
Est. Cost of Outfit: $5,000-$10,000*

For the 2018 Thanksgiving dinner in Palm Springs, Kris Jenner flaunted an $8,000 Versace ensemble, undeniably over-the-top. Kris, unafraid of bold patterns, begged the question: did she exude lavish royalty or mirror the ballroom curtains?

Her fearless approach to fashion sparked debates, as no design seemed too extravagant for her taste. Kris Jenner’s Thanksgiving attire was a testament to her opulent style, a vivid manifestation of her penchant for making a statement, even if it blurred the line between regal and flamboyant décor.

26. Kendall’s Red Carpet Cutoffs

Year: 2017
Est. Cost of Outfit: Undisclosed

In 2017, Kendall Jenner defied red carpet norms by rocking cutoff jean shorts at Cannes while wearing an Alexander Vauthier Haute Couture top. The Swarovski crystal-embellished waistband attempted to elevate the casual piece, but Kendall’s choice sparked discussions. Could a Tide-to-Go have saved her from this potential mishap, or did she, in her classic Kendall way, effortlessly redefine red carpet glamor?

Whether a fashion mishap or a deliberate statement, Kendall Jenner’s Cannes ensemble showcased her ability to blur the lines between casual and couture, making headlines and turning heads in the process.

27. Kim’s Gym or Glam …?

Year: 2016
Est. Cost of Outfit: Undisclosed

Kim Kardashian’s gym or glam dilemma unfolded at JFK airport in 2016 as she paired an Adidas jacket with a black slip dress and heels. The fusion of sporty and chic elements left observers questioning her style choice. Was it indecision or intentional ambiguity? Kim’s audacious move raised the fashion stakes, presenting a bold clash of genres with no apparent shame.

Whether deemed a fashion crime or a pioneering statement, Kim’s JFK ensemble showcased her fearless approach to style, challenging conventions and sparking conversations about the boundaries of airport fashion.

28. Kylie’s Powder Pink Suit

Year: 2019
Est. Cost of Outfit: Undisclosed

Kylie Jenner’s powder pink suit at the Grammys in 2019 caused a stir as the jacket, scarf, and gloves collided in a chromatic puzzle. With shades of an identity crisis, observers wondered if Kylie had been uncertain or if she possessed a deliberate understanding of her ensemble’s eccentric harmony.

The powder pink suit became a canvas for fashion ambiguity, leaving onlookers questioning the boundary between fashion-forward intention and an ensemble in disarray. Kylie Jenner’s Grammys appearance showcased her knack for pushing sartorial boundaries, whether by design or by accident, creating a memorable style moment.

29. Kim’s Leather, Leather & More Leather

Year: 2021
Est. Cost of Outfit: Undisclosed

Kim Kardashian’s leather, leather, and more leather ensemble in New York City, arriving at a hotel from the airport before the Met Gala in 2021, turned heads. Clad in an abundance of leather and a zipper mask, observers questioned if she had been hiding in the darkness or purposefully making a statement to be noticed.

The ensemble, with its bold and edgy elements, left room for speculation about whether Kim had sought to remain incognito or revel in the attention her distinctive fashion choices often attracted. The zipper mask added an air of mystery, sparking conversations about the fine line between anonymity and intentional fashion flair.

30. Kendall’s Huge Hat

Year: 2017
Est. Cost of Outfit: Undisclosed

Kendall Jenner’s huge beanie and faux golden jewelry stirred intrigue and speculation at Marc Jacobs in 2017. The ensemble, seemingly a nod to 70’s hip hop, raised questions – was Kendall concealing something under her hat, or was it a calculated style choice?

With her knack for pulling off avant-garde looks, Kendall Jenner captivated onlookers, leaving them in admiration and curiosity. The oversized hat added an element of mystery to her already bold and stylish ensemble, prompting the lingering question: what secrets lay beneath?

31. Kylie’s Neon Green Leopard Dress

Year: 2020
Est. Cost of Outfit: Undisclosed

Kylie Jenner’s neon green leopard dress in 2020 showcased the family’s penchant for head-to-toe prints. The vibrant ensemble raised questions about whether the leopard print had been splashed with radioactive ooze, yet Kylie managed to pull it off with her signature style.

The audacious choice, marrying neon green with leopard print, exemplified the family’s fearless approach to fashion. Kylie, known for pushing boundaries, turned heads and transformed potentially outrageous fashion experiments into statement-making ensembles, proving that even unconventional combinations could become trendsetting when embraced with confidence.

32. Kris’s Met Gala Fur Coat

Year: 2019
Est. Cost of Outfit: $5,000- 15,000*

Kris Jenner’s Met Gala fur coat made a statement with its unique winged design, prompting speculation about whether she had forgotten to remove the hanger. The daring combination of the pant onesie and the over-the-top fur coat raised eyebrows, but Kris managed to exude an undeniable sense of style, even when her fashion choices teetered on the unconventional.

Despite the potential for a fashion misstep, Kris Jenner maintained an air of confidence and elegance, showcasing her ability to command attention and leave a lasting impression on the Met Gala red carpet.

33. Kim’s Hole Punched Dress

Year: 2o15
Est. Cost of Outfit: $5,000-15,000*

Kim Kardashian’s hole-punched dress at the 2015 CFDA Fashion Awards danced on the line between playful and a sheer fashion crime. The unique design, reminiscent of hole punchers, carried an element of intrigue, but the daring sheer elements prompted speculation on whether it had pushed the boundaries too far.

The dress left little to the imagination, showcasing Kim’s bold approach to red carpet fashion. While the hole-punched ensemble might have been a divisive choice, it undeniably sparked conversations about the balance between avant-garde experimentation and traditional elegance on the prestigious fashion awards night.

34. Kim’s Many Buckle Mini

Year: 2003
Est. Cost of Outfit: Undisclosed

Kim Kardashian’s many buckle mini in Milan 2023 struggled to buckle up under pressure. The ensemble, adorned with numerous belts, raised questions about its ability to withstand scrutiny. This daring choice, while attempting to make a bold statement, might have inadvertently fallen victim to the pressures of fashion critique.

The myriad of buckles might not have provided a secure escape from what could have been perceived as a fashion fail. Kim, known for pushing boundaries, occasionally found herself in the crosshairs of critique, proving that even the trendsetters were not immune to the occasional style misstep.

35. Kris’s Eggplant Mini Puff

Year: 2009
Est. Cost of Outfit: Undisclosed

Kris Jenner’s eggplant mini puff dress at Khloé’s 2009 birthday party in Las Vegas sparked chatter. The vibrant purple hue led to playful speculation – did Kris turn into a blueberry on a Willy Wonka tour?

The eccentric choice, resembling a puffy eggplant, hinted at a fashion misstep. Not even the Oompa Loompas could salvage this ensemble from the realms of a fashion fail. Kris, known for trendsetting, encountered a whimsical hiccup, reminding us that even in the realm of style, unexpected and playful moments were inevitable.

36. Kim’s Surprise Pant Boots

Year: 2o21
Est. Cost of Outfit: Undisclosed

Kim Kardashian’s surprise pant boots, or “Kim-der Surprise!” as it may have been aptly dubbed, showcased a peculiar ensemble that defied clear definition. With Kim seemingly blooming out of her boots, or were they pants? The quirky amalgamation of styles created a totally weird but uniquely Kim look.

Known for her daring fashion choices, Kim Kardashian once again ventured into uncharted sartorial territory, leaving onlookers with a mix of confusion and admiration. The surprise pant boots ensemble exemplified Kim’s ability to challenge conventional fashion norms, turning even the most unconventional pairings into memorable, attention-grabbing moments.

37. Khloé’s Creepy Face Dress

Year: 2021
Est. Cost of Outfit: $100-300*

Khloé Kardashian’s creepy face dress, worn at the Shein x 100K Challenge in 2021, turned heads as it literally gazed back at onlookers. The dress, adorned with many faces, appeared like a nightmare in the making. Despite Khloé’s radiant and fabulous appearance, the attention-grabbing ensemble seemed unsettling.

While Khloé herself was glowing, the dress’s eccentric design might have been a fashion choice that raised eyebrows and prompted conversations. The creepy face dress, with its unconventional charm, captured the essence of Khloé Kardashian’s fearless approach to style, even if it leaned slightly towards eerie.

38. Kylie’s Hat Boot Combo

Year: 2021
Est. Cost of Outfit: Undisclosed

Kylie Jenner’s hat boot combo appeared like a ready-for-the-“Muppet Show” ensemble. If her knees felt cold, her head and feet certainly made up for it, prompting questions about her sartorial choice. The whimsical pairing, accentuated by the addition of a brown leather jacket as a dress, added an extra layer of eccentricity, leaving onlookers pondering Kylie’s vision for this distinctive ensemble.

Renowned for bold fashion statements, this hat boot combo with the unconventional jacket dress highlighted Kylie’s inclination for experimentation, transforming the look into a quirky and attention-grabbing fashion moment.

39. Kourtney’s Mint Ruffle Onesie

Year: 2021
Est. Cost of Outfit: Undisclosed

In 2021, Kourtney Kardashian’s mint ruffle onesie, while promoting her Poosh brand, incorporated a head-to-toe mint-colored ensemble with a ruched blouse and wide-leg pants by Ferragamo.

The outfit, resembling a mint chocolate chip pirate ice cream milkshake promotion, was a bold choice that, if anyone could pull off, it was Kourtney. However, the unique look teetered on the edge of a fashion fail, as the playful combination of ruffles and mint hues might not have resonated with everyone’s style sensibilities. Nevertheless, Kourtney’s confidence and ability to embrace daring fashion choices shone through in this distinctive outfit.

40. Kim’s Velvet Curtain Dress

Year: 2019
Est. Cost of Outfit: Undisclosed

Kim Kardashian donned a dress reminiscent of grandma’s curtains at Kanye West’s Christmas orchestra in New York City in 2019. The bold choice raised eyebrows, but credit was due to Kim for her valor in this unconventional fashion battle.

The dress, adorned with velvety opulence, transformed into a unique ensemble that captured attention. Kim’s fearless approach to fashion was evident in her willingness to embrace unexpected materials and styles, making a statement even if it pushed the boundaries of conventional attire. The velvet curtain dress became a testament to Kim’s daring and avant-garde fashion choices.

41. Kylie Jenner Where’s Your Sweater?

Year: 2017
Est. Cost of Outfit: Undisclosed

Kylie Jenner exited North’s 2017 birthday bash sporting just a quarter of a sweater, in a quirky twist reminiscent of a dog eating homework. Whether her sweater fell victim remained uncertain.

Despite the unexpected fashion statement, Kylie’s arms stayed warm in this avant-garde approach. Blending unpredictability with style, it showcased the carefree attitude fashion icons like Kylie could exhibit. The quarter-sweater moment transformed into a major fashion statement, adding a layer of relatability to the ever-evolving world of high-profile fashion.

42. Khloé’s Fishnet Bodysuit

Year: 2019
Est. Cost of Outfit: $500-15,000*

In 2019, Khloé Kardashian stole the spotlight while celebrating her best friend’s birthday in Las Vegas, clad in a fishnet bodysuit that was pure bait — a major head-turner. The outfit’s mesh intensity prompted speculation, but Khloé, indifferent to opinions, owned the bold choice.

The fishnet bodysuit became a statement of unwavering confidence, showcasing Khloé’s commitment to pushing fashion boundaries. For her, the outfit wasn’t too mesh; it was a deliberate and fearless style move that amplified her daring and trendsetting presence in the dynamic world of fashion.


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