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.
OLD MONEY OUTFITS: THE GUIDE TO NAILING THE EXPENSIVE AND ELEGANT LOOK
Do you crave an aura of understated sophistication? Then the “old-money” aesthetic might be your perfect style match. This timeless approach to fashion transcends fleeting trends, embodying elegance and quality. Forget loud logos and flashy displays of wealth. The old-money look whispers of confidence and heritage through impeccably tailored pieces and a carefully curated wardrobe.
This guide will unveil the secrets to achieving this coveted aesthetic. We’ll delve into the essential garments, explore tips for building a versatile capsule wardrobe, and even touch upon where to find these timeless treasures. So, get ready to cultivate an aura of effortless elegance and discover the art of dressing like you’ve always belonged.
DAY-TO-NIGHT ELEGANCE
Day-to-night elegance is the art of seamlessly transitioning your outfit from workday chic to evening sophistication. It’s ideal for busy schedules that don’t allow for a complete outfit change. By incorporating versatile pieces and strategic layering, you can create a look that’s both polished for the office and glamorous for a night out. Think a tailored dress paired with a blazer for work, then ditch the blazer and add statement earrings for an instant evening transformation. It’s all about maximizing your wardrobe’s potential and letting your confidence shine through as the day fades into night.
A BLAZER
The perfectly tailored blazer is an essential piece for achieving that classic old-money style. The most important thing is getting a great fit – a blazer that hugs your shoulders comfortably and follows the lines of your body without feeling too tight. Throw it on over a crisp button-up shirt and tailored pants for a polished work look, or wear it with a silky slip dress for an effortlessly elegant evening outfit. The blazer’s versatility makes it a must-have for adding a touch of class and timeless sophistication to any old-money inspired ensemble.
SUITS AND TAILORING
Forget about ordinary suits. In the old-money world, a suit is a statement – a declaration of both elegance and quiet power. Bespoke tailoring is key, transforming fabric into a one-of-a-kind masterpiece that reflects your unique style. Classic colors like navy, charcoal, and rich browns rule the roost, with subtle patterns like pinstripes or checks adding a touch of personality without going overboard. Here, a suit isn’t just clothing; it’s a bespoke work of art, meticulously crafted to flatter your form and exude effortless sophistication.
ALFRESCO DINING ATTIRE
Alfresco dining calls for a refined yet relaxed interpretation of old money style. Think lightweight linen blazers paired with crisp white button-downs for men, while women can opt for flowy maxi dresses in muted tones or dark jumpsuits like in this picture. Key pieces include cashmere sweaters, straw hats, and loafers for a touch of effortless elegance. The overall aesthetic should exude a sense of understated luxury, as if the attire is as natural and effortless as the outdoor setting itself.
DRESS SHIRTS AND BLOUSES
Crisp shirting forms the backbone of many old-money outfits. For dress shirts, look for impeccable tailoring in poplin or oxford cloth. Classic white is a must-have, but don’t shy away from subtle stripes or light blues. In blouses, silk or cotton with feminine silhouettes reign supreme. Think pussycat bows, peter pan collars, or timeless button-down styles. Keep embellishments minimal and focus on quality fabrics and a perfect fit. These tops will effortlessly transition from office attire to elegant evening wear when paired with the right separates, creating a foundation for endless old-money inspired looks.
CHIC SWIMWEAR ENSEMBLES
Ditch the flashy neon bikinis! When it comes to swimwear for old-money vibes, think understated elegance that whispers luxury. High-waisted bottoms with a flattering cut are a must, offering a timeless silhouette. Pair them with a bandeau top for a touch of sophistication or a classic triangle top for a bit more coverage. Solid colors in black, navy, or white exude quiet confidence, while a subtle stripe can add a touch of personality. Don’t forget a chic cover-up – a flowy kimono or a tailored linen shirt adds a touch of glamour and ensures a polished look poolside or on the beach. Remember, old-money style is all about quality fabrics and a timeless aesthetic that lets your confidence shine through.
POLO SHIRTS
The polo shirt can be a great way to incorporate a touch of casual elegance into your old-money wardrobe. Here’s the key: elevate the classic piece with a focus on quality and details. Opt for pique cotton, a heavier and more luxurious fabric compared to standard polos. Stick to classic colors like navy, white, or cream. Skip bold logos or busy patterns – a clean, well-fitting silhouette speaks volumes. The fit should be neither baggy nor too tight – think a tailored polo that skims your shoulders and flatters your form. Pair it with chinos or tailored shorts for a relaxed yet polished look that embodies the understated sophistication of old-money style.
ELEGANT ACCESSORIES
Elegant accessories for old money outfits exude timeless sophistication and understated luxury, perfectly complementing the refined aesthetics of such ensembles. These accessories often include classic pearl necklaces, simple yet stunning diamond stud earrings, and gold or silver cufflinks that add a subtle touch of opulence. Leather belts and handbags in neutral tones offer a polished finish without overpowering the outfit. Silk scarves in muted colors or traditional patterns can be draped elegantly over the shoulders or tied around the neck for a sophisticated flair. Watches with clean, minimalist designs and high-quality leather straps or metal bands signify both elegance and wealth without being ostentatious. Well-crafted, polished shoes, such as loafers or brogues for men and ballet flats or low heels for women, complete the look, ensuring an air of quiet confidence and impeccable taste. These accessories embody the essence of old money style, characterized by quality, restraint, and an appreciation for the finer, more subtle details in fashion.
DRESS PANTS AND SKIRTS
Dress pants and skirts for old money outfits exemplify classic tailoring and sophisticated style, ensuring a polished and timeless appearance. These garments are often crafted from high-quality materials such as wool, silk, or cashmere blends, providing both comfort and durability. Dress pants feature clean lines, tailored fits, and sometimes subtle pleats, offering a sleek silhouette that pairs well with crisp button-down shirts or elegant blouses. Skirts in old money wardrobes typically include pencil skirts, A-line designs, and midi lengths, all of which convey an air of elegance and refinement. Neutral colors like black, navy, beige, and gray dominate the palette, though understated patterns such as houndstooth or pinstripes may occasionally be seen. These skirts and pants are designed to be versatile, easily transitioning from daytime professional settings to evening social events with the right accessories. The emphasis on impeccable fit and timeless design ensures that these pieces remain stylish and relevant for years to come, embodying the essence of old money fashion with their understated yet powerful presence.
SOPHISTICATED SEPARATES
Sophisticated separates for old money outfits epitomize timeless elegance and effortless chic, offering versatility and refinement for various occasions. These pieces include impeccably tailored blazers, high-quality knit sweaters, and crisp button-down shirts, all designed to be mixed and matched seamlessly. Fabrics such as cashmere, silk, linen, and fine wool are chosen for their luxurious feel and durability. The color palette tends to focus on classic neutrals—navy, ivory, camel, and charcoal—complemented by subtle patterns like herringbone, stripes, or checks. Trousers are often high-waisted and well-fitted, while skirts maintain a modest length and structured form, such as A-line or pencil styles. These separates are designed to layer effortlessly, creating a cohesive and polished look that easily transitions from casual daywear to more formal evening settings. The emphasis on quality craftsmanship and timeless design ensures these pieces remain wardrobe staples, embodying the understated luxury and enduring style that are hallmarks of the old money aesthetic.
DRESSES AND GOWNS
Dresses and gowns in old money outfits exude an air of timeless sophistication and classic elegance, perfect for a variety of formal and semi-formal occasions. These garments often feature high-quality fabrics such as silk, satin, chiffon, and lace, chosen for their luxurious texture and graceful drape. The designs tend to be understated yet refined, with clean lines, modest necklines, and tasteful embellishments like delicate beading or subtle embroidery. Colors are typically muted and elegant, including shades of black, navy, ivory, and deep jewel tones, ensuring a sophisticated and versatile look.
MONOCHROME MAGIC
Monochrome magic in old money outfits showcases the power of simplicity and elegance through a single-color palette, creating a cohesive and sophisticated look. This style leverages various shades and textures within the same color family to add depth and interest while maintaining a polished and refined appearance. Monochrome ensembles often feature luxurious fabrics such as cashmere, silk, wool, and fine cotton, which contribute to the overall richness of the outfit. The key to mastering monochrome magic lies in the attention to detail and quality of each piece. By focusing on impeccable tailoring, high-quality materials, and subtle variations in texture, monochrome outfits can be both visually captivating and timelessly chic.
PRINTS WITH PANACHE
Prints with panache in old money outfits bring a touch of boldness and personality to an otherwise classic and refined wardrobe. These prints are often characterized by their timeless appeal and subtle sophistication, rather than loud or trendy patterns. Key prints include elegant florals, tasteful stripes, houndstooth, and classic plaids, all designed to add visual interest without overwhelming the ensemble. When incorporating prints with panache, the focus should remain on quality and fit, ensuring each piece complements the overall aesthetic. Accessories should be kept minimal to allow the prints to shine, with simple jewelry, classic handbags, and understated shoes completing the look.
LUXE COTTON PAIRINGS
Luxe cotton pairings for old money outfits highlight the perfect blend of comfort and sophistication, utilizing high-quality cotton fabrics to create polished and timeless looks. These ensembles often feature crisp cotton shirts, tailored trousers, and structured blazers, all characterized by impeccable craftsmanship and attention to detail. Classic cotton button-downs, whether in solid colors or subtle patterns like pinstripes, serve as versatile staples that can be effortlessly paired with well-fitted cotton trousers or skirts. Neutral tones such as white, navy, beige, and soft pastels dominate the color palette, ensuring a cohesive and elegant appearance. Accessories, including leather belts, understated jewelry, and classic loafers or ballet flats, complement the luxe cotton pieces without overpowering them.
BREEZY LINEN LAYERS
Breezy linen layers in old money outfits capture the essence of effortless elegance and timeless sophistication, perfect for warm-weather dressing. Linen, known for its lightweight and breathable qualities, is a staple in creating ensembles that are both comfortable and chic. Classic linen pieces such as tailored trousers, relaxed blazers, and flowing dresses serve as the foundation of these outfits. Neutral shades like ivory, beige, soft grey, and muted pastels are favored, reflecting a refined and minimalist aesthetic.
BUILDING A TIMELESS WARDROBE: KEY ESSENTIALS AND INVESTMENT PIECES
The old-money aesthetic isn’t about fleeting trends; it’s a celebration of enduring quality and effortless elegance. Building a wardrobe that reflects this philosophy requires focusing on pieces that transcend seasons and transcend your closet. Here’s how to curate a collection that whispers luxury and whispers longevity:
Tailored Blazers & Trench Coats: Consider a well-tailored blazer and a classic trench coat your sartorial armor. These versatile heroes can be thrown on year-round, effortlessly transforming your look for any occasion.
Cashmere’s Enduring Embrace: Indulge in a high-quality cashmere sweater – a luxurious investment that offers practicality too. It seamlessly transitions from casual weekend wear to a sophisticated evening ensemble.
Silk Blouses: A Touch of Timeless Femininity: A silk blouse is a wardrobe workhorse. Its inherent elegance adds a touch of femininity and sophistication to any outfit, making it a must-have for achieving old-money polish.
A-Line Skirts & Wool Trousers: Flattering Forms, Classic Appeal: Embrace the timeless silhouettes of A-line skirts and wool trousers. These universally flattering pieces offer endless outfit possibilities, working wonders for various body types.
The Little Black Dress: No wardrobe is complete without a little black dress. This timeless wonder transitions flawlessly from business meetings to evening dinners, ensuring you’re always dressed to impress.
Quality Footwear: The Foundation of a Polished Look: Invest in leather flats, classic pumps, and comfortable yet stylish boots. Quality footwear not only offers lasting comfort but also elevates your outfit with a touch of undeniable elegance.
The Leather Handbag: A Timeless Legacy: A high-quality leather handbag is an heirloom in the making. It elevates any outfit while standing the test of time, both in terms of style and durability.
By investing in these key pieces, you’ll cultivate a wardrobe that embodies not just the old-money aesthetic but also a commitment to quality craftsmanship. These timeless garments will become the foundation of your style, allowing you to mix and match with confidence, ensuring you’re always impeccably dressed for any occasion.
ADOPTING AN OLD MONEY MINDSET AND ETIQUETTE
The old-money aesthetic is more than just a collection of well-tailored garments; it’s a philosophy woven into the very fabric of your being. It’s about cultivating a certain grace, a quiet confidence, and a respect for tradition that whispers of a cultured and educated background. Here’s how to embody this spirit in your everyday life:
The Art of Conversation: Master the art of thoughtful speech and attentive listening. Eschew gossip in favor of engaging in meaningful conversations that showcase your genuine interest in others.
Manners Maketh the Man (or Woman): Polish your table manners, be punctual, and treat everyone with respect, regardless of their station. True refinement shines through genuine courtesy in every interaction.
A Well-Stocked Mind: Stay informed about current events and cultivate a diverse range of interests. This allows you to contribute intelligently to conversations and engage with the world around you in a meaningful way.
Discretion is the Better Part of Valor: Value your privacy and the privacy of others. Old-money style thrives on understatement – avoid oversharing or flaunting wealth. Let your accomplishments and character speak for themselves.
Embracing this mindset is the key to truly living the old-money lifestyle. It’s about more than just looking the part – it’s about embodying the values and behaviors that define this timeless aesthetic. When you cultivate grace, respect, and a love of learning, you’ll project an aura of quiet confidence that transcends trends and speaks volumes about your inner world.
CONCLUSION
In conclusion, mastering the old-money aesthetic isn’t about chasing expensive labels or fleeting trends. It’s about building a wardrobe of well-crafted, timeless pieces that exude quality and effortless elegance. By prioritizing quality over quantity, and incorporating versatile staples that can be mixed and matched, you can cultivate a collection of classy outfits that will carry you through any occasion. Remember, the old-money aesthetic is as much about cultivating a certain grace and confidence as it is about the clothes you wear. So, embrace the values of quiet sophistication, timeless style, and a hint of understated luxury, and let your inner old-money elegance shine through.
