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19 MOST TALKED-ABOUT KYLIE JENNER OUTFITS OF ALL TIME

Each of the five Kardashian-Jenner sisters has had their own fashion journey. Kim loves a sensual style with a sporty touch, Kourtney has moved from trendy to grungy, Khloe favors stylish activewear, and Kendall’s model-off-duty look is clean and chic. Kylie Jenner’s outfits, however, are often more surprising than her older sisters’.

From bold colors to body-hugging styles and simple French-girl looks, you never know what Kylie will wear next. We love that she keeps us guessing! While her sisters have clear styles, Jenner enjoys trying out different looks, and with so many designers available to her, it makes sense to mix things up.

Kylie Jenner’s outfits—whether on the red carpet or in everyday life—offer lots of fashion ideas for everyone. To help you keep track of the beauty mogul and mom of two’s best looks, we’ve picked out some of our favorites.

KYLIE JENNER IN L.A. IN AUGUST 2018

The Kardashian-Jenners are all about that Barbie vibe, and Kylie is definitely no exception. It’s hard to pick what we love most about this look—the stunning dress, the chic shoes, or the sleek platinum ponytail!

KYLIE JENNER AT THE MTV VMAS IN 2018

There’s no need to tell you that the business owner and founder is a boss; this sharp blazer dress outfit speaks for itself.

KYLIE JENNER IN N.Y.C. IN NOVEMBER 2018

Why go for denim-on-denim with separates when you can nail the Canadian Tuxedo look with a stylish jumpsuit? This all-denim outfit is definitely one we can support.

KYLIE JENNER AT THE GRAMMY AWARDS IN 2019

Balmain suits Jenner perfectly, as shown by this blush pink jumpsuit with dramatic sleeves she wore to the Grammys. We imagine this one-piece is as comfy as it is beautiful; it’s a nice change from her usual body-hugging dresses, and we love it!

KYLIE JENNER AT THE MET GALA IN 2019

At one point, Jenner had a purple phase. She brought back her signature color for the 2019 Met Gala and perfectly captured the “Camp: Notes on Fashion” theme.

SOPHISTICATED SEXY

For the premiere of Travis Scott: Look Mom I Can Fly, Jenner chose an outfit that exuded sophistication. The white bodycon dress highlighted her signature curves, while the sexy back cutouts added a fun twist. We also loved the addition of the bow choker!

KYLIE JENNER AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2021

This mermaid-style gown from Ralph and Russo combines sparkly fun with Old Hollywood glamour. Jenner said the look was worth it, even though it made sitting down a bit tricky!

KYLIE JENNER IN L.A. IN MARCH 2021

Is it just a coincidence that Jenner wore a strikingly similar outfit to celebrate the Haqq sisters’ birthday in 2023, just like she did in 2021 at the same venue? The only difference is the color: red instead of black. It just goes to show that even celebrities repeat outfits—sort of!

KYLIE JENNER AT THE BALMAIN SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022

Having designer friends definitely pays off, especially when they create exclusive looks just for you. Jenner has been a muse for many designers, but this crochet minidress by Balmain’s Olivier Rousteing is one of our top five favorites.

KYLIE JENNER IN PARIS IN SEPTEMBER 2022

Jenner is a strong supporter of the underwear-as-outerwear trend. She paired white hipster briefs with a matching tank top, black tights that blend into her boots, and a grey overcoat on top—simple yet absolutely showstopping!

KYLIE JENNER AT THE THE BOF 500 GALA IN PARIS IN 2022

Jenner is no stranger to a mesh look, but this outfit from the Business of Fashion 500 gala in Paris last fall really caught our eye. Custom-made for her by Casey Cadwallader, the creative director of Mugler, it features a stunning design of asymmetrical lace.

KYLIE JENNER AT THE COPERNI SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022

Although Jenner has recently been seen in more neutral tones, she’s always been “a big fan of color,” as Lizzie McGuire’s Miranda Sanchez would say. She particularly shines in blue, making the floral minidress she wore front row at the Coperni Spring/Summer 2023 show a must-have on this list. Don’t miss the matching sunglasses and heels!

KYLIE JENNER IN N.Y.C. IN NOVEMBER 2022

Jenner has certainly influenced many street style trends, but we think she may have borrowed the no-pants look from her big sister Kendall. Regardless, she nails the leggy style with a neutral base, an oversized black trench coat, and pointed-toe heels.

KYLIE JENNER IN ARCHIVE MUGLER AT THE MUGLER COUTURISSIME OPENING IN N.Y.C. IN 2022

At the Mugler Couturissime exhibition opening, Jenner called herself the “Mugler king” on Instagram. Given that it’s been almost a year since the event and we’re still talking about her look, we definitely agree! The Morticia Addams-inspired corset dress is fabulous on its own, but her headpiece would have turned heads even without it.

KYLIE JENNER IN PARIS IN FEBRUARY 2023

Remember when Jenner experimented with bright pastel hair colors? Well, blue is still her go-to! For an afternoon stroll in Paris, the mom of two wore a long-sleeved, body-hugging midi dress in a striking blue shade, pairing it with glittering Barbie-pink boots.

KYLIE JENNER IN L.A. IN MARCH 2023

It’s no surprise that for Malika and Khadijah Haqq’s 40th birthday, the youngest Jenner celebrated in style. The Kylie Cosmetics founder dazzled in a sexy set featuring a satin miniskirt and a matching black satin peek-a-boo mesh top. She completed the look with a leather trench coat, sheer black tights, and pointed-toe heels.

KYLIE JENNER IN MAISON MARGIELA AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2023

Maison Margiela custom-made Jenner’s stunning metallic gown for the 2023 Vanity Fair Oscar Party, and the design did not disappoint. The original piece featured a statement bow tied at the bust and a cape train flowing from her mid-back. The only way this look could have been better is if the beauty mogul arrived in the Batmobile, because it’s definitely giving “superhero, but make it fashion.”

KYLIE JENNER IN JEAN PAUL GAULTIER AT THE MET GALA IN 2023

If anyone knows how to make a statement on the red carpet, it’s Kylie. The Haider Ackermann for Jean Paul Gaultier gown she wore to the 2023 Met Gala turned heads with every step. With its asymmetrical neckline, cold shoulder, and high thigh slit, this fiery ensemble was undoubtedly one of her best looks.

KYLIE JENNER IN PARIS IN MAY 2023

Jenner made a splash in the quiet luxury trend while in Paris. The reality star wore a crisp white midi dress with a corset waist and matching heels, keeping her accessories simple with small silver hoops, black sunglasses, and a tiny white handbag.

CONCLUSION

Kylie Jenner’s impact on the fashion world is undeniable. Her bold, daring, and often trendsetting outfits have captivated audiences worldwide, cementing her status as a style icon. From her early days as a reality TV star to her current role as a successful businesswoman and influencer, Jenner’s fashion choices have continued to evolve and inspire.

The outfits featured in this list represent just a glimpse of Jenner’s extensive style repertoire. Her ability to seamlessly blend high fashion with streetwear, her willingness to experiment with bold trends, and her knack for creating iconic looks have solidified her place in fashion history. As Jenner’s career continues to flourish, it is clear that her influence on the fashion industry will only grow stronger.

HOW TO STYLE A BLAZER: ELEVATE YOUR WARDROBE WITH TIMELESS FLAIR

Keeping up with ever-changing trends can be challenging, but a timeless blazer is always a reliable choice for adding a splash of color to any outfit. This versatile jacket has moved beyond the office, seamlessly fitting into even the most casual looks. While a button-down shirt is a classic, effortless combination, taking a closer look at street style stars reveals innovative ways to refresh this classic pairing. To uncover those fresh styles, keep reading.

WITH A BIT OF FRINGE

A blazer with a bit of fringe adds a touch of bohemian flair to any outfit. The delicate tassels or fringes can be on the lapels, cuffs, or hemline, creating a subtle or dramatic effect. This detail can instantly elevate a classic blazer, making it perfect for both casual and formal occasions. Whether you choose a fringe blazer in a neutral color or a bold pattern, it’s sure to become a statement piece in your wardrobe.

WEAR WITH JEANS

Absolutely, a blazer pairs perfectly with jeans! For a casual look, try combining a blazer with jeans and sneakers. This effortlessly stylish combo brings a laid-back vibe to your blazer. Opt for distressed denim and sneakers for an off-duty street style feel, or go with clean, tailored straight-leg jeans and ballet flats for a polished touch. You can also rock a cropped blazer with wider-leg jeans for a chic, balanced look.

WITH A BRIGHT SKIRT

A blazer paired with a bright skirt is a dynamic and visually captivating combination that effortlessly exudes confidence and style. The juxtaposition of the tailored, structured blazer with the vibrant, flowing skirt creates a harmonious yet unexpected contrast. The blazer adds a touch of sophistication and polish, while the skirt infuses the ensemble with a burst of energy and personality. 

WITH FUNKY ACCESSORIES

Refresh your daily outfits by incorporating the season’s standout funky accessories. With a range of unconventional shapes and styles available, these unique pieces can elevate even the most casual looks.

With Cut-Offs

A slouchy blazer in a fun color adds the perfect finishing touch to an outfit that mixes high and low fashion. Pair it with a basic white tank and cut-off shorts for a chic backdrop that highlights a statement bag.

WITH A SCARF ON TOP

Draped over the shoulders or tied around the neck, a scarf adds a touch of elegance and personality to any blazer ensemble. The interplay of textures and patterns between the blazer and the scarf creates a visually captivating effect. A silk scarf can infuse the outfit with a touch of luxury, while a chunky knit scarf adds warmth and coziness.

THE DOUBLE-DENIM BLAZER OUTFIT

A modern take on the classic Canadian tuxedo is a must-have for any stylish wardrobe. Embrace the ’80s shoulder and add a denim blazer to your rotation. This versatile piece can be dressed up or down and is a timeless addition to your wardrobe.

WITH TAILORED TROUSERS

If you’re spending more time in the office, pair a blazer with tailored trousers for a smart, stylish summer work outfit. While traditional suits might feel dated, coordinating your blazer with your trousers is a fresh, modern choice. To keep it contemporary, opt for vibrant sherbet shades or pretty pastels instead of plain black, if your job allows. Alternatively, mix neutral trousers with patterned or colored blazers for a dynamic look.

WITH MIDI DRESSES

Midi dresses are essential wardrobe staples that can be dressed up or down with ease. Pair them with a blazer for a chic and versatile look that’s perfect for work, cocktail hour, or any occasion in between. Experiment with different blazer styles to create unique looks. An oversized blazer adds a relaxed vibe to a slip dress, while a shorter belted jacket gives a vintage twist to a printed midi. For a sleek and modern look, try styling a blazer in the same color as your dress.

WITH LEGGINGS

A blazer paired with leggings is a chic and comfortable ensemble that effortlessly blends casual and sophisticated elements. The contrast between the tailored blazer and the relaxed leggings creates a visually striking and modern look. The blazer adds a touch of polish and structure, while the leggings offer comfort and flexibility.

CONCLUSION

The blazer, once a formal staple, has evolved into a versatile and essential piece in modern wardrobes. By exploring different styles, colors, and pairings, you can elevate your outfits and express your personal style.

From classic combinations to bold and trendy looks, there’s a blazer for every occasion and taste. Whether you’re heading to the office, a casual outing, or a special event, a well-styled blazer can add a touch of sophistication, confidence, and timeless flair. So, embrace the versatility of the blazer and experiment with different styles to discover your signature look.