She regularly wore trendy two-piece outfits in the early 2000s and an assortment of minidresses — like the brown knit piece she sported at the 2002 Environmental Media Awards.

Sánchez Bezos also had a signature pair of shoes at that point in her career: PVC sandals with light-brown soles and thin, see-through heels.

At the 2004 Shalom Foundation Gala, Sánchez Bezos donned a deep-gray gown that hugged her body at the bodice and reached the floor with its long skirt.

It was also practically strapless, with only a single spaghetti-thin strap across one shoulder. The piece connected to more strings across its open back, which held the dress up and created a daring detail.

Sánchez Bezos completed the outfit with crystal earrings and a silver statement watch.

While attending a High Flying fundraiser in 2008, Sánchez Bezos opted for trendy styles at the time: a high-neck, short-sleeve blouse tucked into a black-and-white circle skirt, knee-high boots over semi-sheer tights, and a leather belt.

But her purse was timeless. She carried a solid black Hermès Birkin bag with what appeared to be palladium hardware.

She attended Vanity Fair's Oscars after-party that year in a shimmering gown that was fit for an award winner.

The dress was sleeveless, form-fitting, and covered from top to bottom in silver sparkles. It also had a tan lining that gave the dress a nude illusion and a deep V-neckline.

At the 2012 Vanity Fair Oscars after-party, Sánchez Bezos sported a strapless, understated gown. It had a fitted bodice, a straight skirt, and solid fabric.

But its bright red shade stood out on the carpet, making for a memorable look. The color has become one of Sánchez Bezos' go-to shades in recent years.

She completed the look with platform sandals and diamond jewelry.

She wore a black-and-red dress that was as daring as it was glamorous. It featured long sleeves made from dotted mesh, a plunging neckline that reached her navel, and a thigh-high slit that showed her platform sandals.

The piece also had a geometric print crafted from sequins that shimmered in the light.

The couple attended the 2023 Vanity Fair Oscars after-party in matching black outfits. While Bezos sported a classic suit, Sánchez Bezos wore a bold Elie Saab gown.

The dress had a corseted bodice with off-the-shoulder sleeves, black sparkles arranged in stripes, and a see-through skirt that revealed her legs.

At the 2023 Kering Caring for Women dinner, for example, Sánchez Bezos sported a neon-yellow gown from Dolce & Gabbana.

The halter dress hugged her body, reached the floor, and didn't need any accessories. It sparkled entirely on its own.

Sánchez Bezos and Bezos attended a 2024 state dinner hosted by Joe Biden in honor of then-Japanese Prime Minister Fumio Kishida.

Though the couple's presence was notable on its own, Sánchez Bezos' outfit caught even more attention.

She wore an off-the-shoulder gown crafted from red satin and lace. Its corseted bodice was semi-sheer with a low neckline, and its skirt was tightly wrapped around her legs.

Sánchez Bezos wore it with gold-leaf sandals and diamond earrings.

She stunned in an Oscar de la Renta gown. It featured a strapless black bodice with a sweetheart neckline and a full skirt decorated with reflective pieces shaped like roses.

It was even rumored that Anna Wintour had a hand in the outfit choice.

At the Forbes Power Women's Summit in September 2024, Sánchez Bezos talked about the start of her career, writing her first children's book, and being engaged to Bezos.

For the occasion, she sported an all-white outfit with long trousers, a blazer that revealed her lace bralette, and platform heels.

After wearing her McQueen suit to the Forbes panel in September and a New York Times book event in December, she donned it again at Donald Trump's inauguration.

This time around, however, she paired it with another daring piece: a Schiaparelli coat made from brushed wool, mohair, and gold-brass buttons designed to look like nipples.

The Italian piece retailed for 8,700 euros, or about $9,982.

While the Amazon founder wore a black suit with a white undershirt, a matching bow tie, and a diamond brooch, Sánchez Bezos donned a strapless white Oscar de la Renta ball gown.

It had a feather fringe, a mermaid silhouette, and was accessorized with an emerald necklace.

The couple married a few months later in June 2025.

For the 2026 Met Gala, Sánchez Bezos wore a Schiaparelli gown crafted from navy blue satin.

It had a V-shaped neckline, a short train, and crystal straps — one of which hung off her shoulder.

The dress, inspired by the 1884 painting "Madame X," doubled as a hidden message to those who have criticized her daring fashion choices.

In June, the author was photographed wearing an outfit that blended casual and high-end styles.

She wore a blue knit dress lined with silver shimmering mesh at the hem and neckline.

To complement the latter details, she added a metallic clutch, diamond earrings, and tan Louboutin heels.

The black gown was asymmetrical with a single strap, an uneven cutout across her waist, and smaller slits down its skirt that extended the length of her leg.

She accessorized the bold look with crystal-lined gloves, a satin choker, semi-sheer tights, and knee-high boots.

She wore a form-fitting halter dress that was most daring up top, with a plunging, scooped neckline.

Twain donned the glittering, gold gown with diamond jewelry, long earrings, and her hair styled in curls.

Her black, long-sleeved dress was made from sheer mesh, but it was wrapped with opaque black fabric and matching straps. It also had a tulle piece attached to one side of its skirt that created a short train.

To complement the unique look, Twain also wore a crimped hairstyle and thigh-high lace-up boots.

Her outfit included a crystal-covered bra, black shorts over fishnet tights, a sparkling black duster jacket, and a sequined white belt that wrapped around her waist and hips.

She also wore thigh-high leather boots.

Twain performed onstage in low-rise black cargo pants and a puffer vest buttoned only halfway.

The latter piece had a green, black, and pink swirled print that perfectly matched the design of her slouchy boots.

The long-sleeved, high-neck piece was decorated from top to bottom with black beads in a tiger-stripe print, and her black gloves were lined with long, fabric fringe.

She wore the outfit with heeled, belted boots.

She hit the stage in a red catsuit with a plunging neckline and a sparkling chainmail piece worn over it.

Twain also rocked furry boots, a matching jacket, and red leather gloves.

She walked the People's Choice Awards red carpet in a custom Rodarte dress. It had a sheer, long-sleeved bodice, a leopard-print bralette, and a floor-length velvet skirt with a waistline that dipped below her belly button.

The outfit — which seemingly called back to her ensemble from the "That Don't Impress Me Much" music video — also included a leopard-print hood and shoulder piece.

Harris Reed designed her black-and-white polka-dot look. It featured bell-bottom pants, a bustier top, and a blazer worn on top.

She first walked the red carpet in a butterfly-print dress, but later changed into a sparkling purple Chanel set that included a crop top and matching shorts. 

When some people on social media criticized the look, particularly the cut of her shorts and the plunging neckline of her top, Twain defended her daring outfit.

"For me fashion is a powerful tool that helps to convey my personality and express my creativity," she wrote in an Instagram post. "And other than getting to hang out with my friends for the night, it's one of my favourite things about attending award shows!"

She wore a pink, loose-fitting top over what appeared to be a yellow leotard, and matching jelly sandals with straps that wrapped around her legs.

The black garment was covered in crystals, as were her fishnet tights and knee-high boots.

To complete the outfit, Twain also wore a pink-and-purple cape that flowed behind her and layers of chunky necklaces.

In collaboration with Levi's, Twain helped design her denim evening gown.

The halter piece had a form-fitting bodice, a mermaid skirt, a thick, pointed collar, and all-over crystal detailing.

She wore the dramatic dress with denim gloves, a chunky ring, and a '60s-inspired hairstyle.

The silver, strapless gown was designed by Falguni Shane Peacock.

It was covered in silver and black sequins, the latter of which were arranged in the shape of a panther across its skirt.

The dress, which was accessorized with black leather gloves, also had satin strips that flowed from her waist.

Taylor, who was nominated for best supporting actress for "One Battle After Another," donned a white Chanel gown for the after-party.

The front of the slip-style, floor-length dress was simple, with a V-neckline and ruched bodice, while the plunging back was anything but. The straps were adorned with gold thread, and stars were embroidered on each strap. It was a celebratory and sexy look.

She hit the carpet in a black, sleeveless romper and semi-sheer tights. The Dior piece had a cowl neckline, a small mesh cutout across the chest, and extra-short shorts.

It was so simple that it didn't match the actor's standout Tiffany & Co. diamond necklace or her bow-shaped hat.

The "Sinners" star celebrated winning his first Oscar in a brown suit, which included a double-breasted jacket and wide-legged trousers.

Three brooches on his lapel and brown sunglasses made the outfit pop.

Her golden Stella McCartney gown, which was sleeveless and form-fitting, looked glamorous on the actor.

Unfortunately, it was lined with thick brown faux fur along its hem, which contrasted with the glimmering material and distracted from the overall look.

Jenner's Chanel gown hugged her figure. It had a scooped neckline and spaghetti straps, and sparkly embellishments covered the dress from head to toe. Larger embellishments on the neckline and waistline added even more drama.

She paired the gown with Tiffany & Co. jewelry and Gianvito Rossi shoes. It was simultaneously effortless and stylish.

The supermodel arrived at the Vanity Fair party wearing a yellow gown designed by Chrome Hearts. It had a plunging halter neckline and hip-high slits, all covered in embroidered mesh.

The latter detailing didn't work for her. A classic yellow gown without the slits and mesh would have looked more streamlined and elegant.

Tamara Ralph designed Ashley's glittering, floor-length gown. The standout feature of the form-fitting gown was its bejeweled, asymmetrical neckline, seemingly inspired by a peacock feather.

Aquazzura shoes and Buccellati jewelry completed Ashley's look.

Her Gucci look, straight off the runway, featured a high neckline, long sleeves, a floor-length skirt, and all-over sparkles.

On another celebrity, it might have looked striking. On Kardashian, though, it was far too simple. It won't be remembered among her best Oscar-night outfits.

Goth's black Dior gown looked simple from the front, with an arched, strapless neckline and tea-length skirt.

However, the back revealed a short, white skirt made of layers of embroidered, fluffy tulle for a fashion-forward flair.

Many celebrities wore white at the Oscars and the Vanity Fair party. So technically, Vergara was right on trend with her white Zuhair Murad halter gown.

The details of her dress, though, looked more fitting for a bride than a red-carpet star. It had all-over crystals, a diamond-shaped cutout, and flowing white fabric that hung from her shoulders, resembling a veil.

Harris Reed designed the avant-garde gown for the "Marty Supreme" actor.

Voluminous, arched sleeves with tassels sat on her shoulders, giving way to a black bodice with a large cutout in the center of her chest. The rest of the bodice was leopard print, while the skirt was made of layers of multicolored fabric trimmed with the same tassels that sat on her shoulders.

The contrasting elements felt cohesive on A'Zion. She paired the bold dress with Pandora jewelry.

Rita Ora is known for her bold fashion, which usually works for her. At the Vanity Fair party, though, it was tough to focus on a single element of her Tamara Ralph outfit.

She wore a floral embroidered gown that was sheer from her shoulders to her hips. That's where a satin skirt wrapped around her legs and extended into a long train. She also wore a massive feathered hat.

Ditching the latter accessory might have let the dramatic gown shine more.

The "Heated Rivalry" stars both wore sheer, black shirts to the Vanity Fair Oscar party, walking the red carpet together in their matching looks.

Balenciaga designed Williams' sleeveless, high-neck shirt, which billowed slightly and formed a floor-length train. He paired the bold top with black trousers and shoes.

Storrie's Saint Laurent top was more form-fitting, with a high neckline and long sleeves. He also wore black trousers and shoes, but he carried a brown stole and wore a bold Tiffany & Co. choker for added drama.

He wore a gray suit comprising tailored trousers, a white button-up shirt, and a blazer with satin lapels and coattails. In place of a tie, he wore a silver neck scarf with fringe and a small bow.

Though the outfit was eye-catching, it looked a bit like a historical costume. A cropped jacket and a flat neck scarf could have made the outfit sharper.

Designed by Celia Kritharioti, the halter neckline of Union's silver gown plunged to nearly her navel, while the back was completely open. She played up the sparkles in the gown's fabric with Tiffany & Co. jewelry, including a bold pendant that sat on her chest.

Union looked glamorous and sexy for Vanity Fair's event.

She arrived at the party in a black Alexander McQueen design. It had a halter top with a deep V-neckline, shining fabric that hugged her body, and a feathered skirt and train.

Though the dark color looked strong on Jenner, its design was a bit too simple.

It also had an odd triangular cutout at the hip, which made the dress appear unfinished.

Domingo's Jacquemus suit put a fun twist on a pinstripe look, as the stripes were silver instead of white. His collar was popped on one side and folded over on the other, offering an asymmetrical look.

Domingo brought even more glamour to his outfit with a brooch and jewelry from Boucheron.

Palmer walked the red carpet in a purple, velvet Gucci set. The long-sleeve, high-neck top was actually a bodysuit, and the low-waisted, floor-length skirt revealed peeks at Palmer's hips.

The outfit had some cool elements, but it ended up looking pretty one-note on Palmer because of the heavy fabric. A more interesting fabric or a different neckline may have brought more dimension to the look.

The longtime couple walked the Vanity Fair red carpet together in beautiful black-and-white ensembles.

Waterhouse's two-piece from Tamara Ralph featured a backless, metallic top that looked like peacock feathers curving around her body. The high-waisted skirt was fitted, and a floor-length, sheer cape trailed behind Waterhouse. She wore Stuart Weitzman shoes and Messika jewelry.

Pattinson's tuxedo suit was pretty simple, but he made it fun by wearing a brooch on his neck instead of a tie.

Louis Vuitton designed the Olympic champion's black dress, which was adorned with gray and black textured embellishments.

The dress was cool, and it was fun to see Liu wear it with black tights and pointed-toe heels. However, the garment's high neckline and boxy sleeves looked ill-fitting on Liu's small frame. A dress with a softer shape would have worked better for Liu.

Louis Vuitton designed Mosaku's lilac ensemble for the Vanity Fair party.

The strapless dress was embroidered with a floral pattern, which she paired with a floor-length train made of layers of purple fabric that looked like flower petals.

Mosaku was nominated for best supporting actress for "Sinners" at the Oscars.

Sánchez Bezos went vintage for the Vanity Fair party, wearing a black John Galliano gown from 1995. The strapless piece had a V-shaped peplum on the waistline, and the slit in the center of the floor-length skirt mirrored its shape.

She leaned into the all-black look with sheer, black tights and Christian Louboutin heels. She also added jewelry by Lorraine Schwartz and Lisa Klein to the ensemble.

While Sánchez Bezos was among the best-dressed of the night, her husband was among the worst. Bezos' black tuxedo was fine for the occasion, but there wasn't anything interesting about it.

She walked the red carpet in a white Givenchy ball gown fit for royalty. The strapless design featured metallic wisteria petals across its bodice and along the bottom of its skirt, which added an elegant sparkle to the look.

Fanning, nominated for best supporting actress for "Sentimental Value," also wore a diamond Cartier choker necklace from 1903. It was shaped like leaves.

The "Hamnet" star, nominated for best actress in a leading role, chose a two-toned look from Chanel.

It had a strapless, off-the-shoulder bodice made of red satin and a flowing, floor-length skirt in baby pink. The gown also had a short train. She completed the elegant ensemble with a diamond tennis necklace and sparkling earrings.

Alwyn, who also starred in "Hamnet," looked sharp at the 2026 Oscars.

He wore a matte-black blazer, matching trousers, and a classic white button-up top with a statement collar. For accessories, he chose a diamond brooch, a silver watch, and a deconstructed satin bow tie.

Moore stunned on the Oscars red carpet in a dramatic, strapless gown. It had long black feathers across the chest, smaller green ones on its bodice, and more feathers decorating its floor-length skirt.

The actor, who is presenting at the show this year, added earrings and a sparkling bracelet to the look.

A presenter at the 2026 Oscars, Culkin walked the red carpet wearing a chocolate-brown suit jacket with black trousers and a matching button-up top.

He also wore flashy gold accessories, including a statement Hublot Classic Fusion Chronograph watch and a glittering brooch.

The "KPop Demon Hunters" voice actor walked the red carpet in a strapless, see-through gown made from sparkling black lace.

Designed by Miss Sohee, the floor-length design hugged her body and was complete with ruffled green arm bands that reached the floor. The latter were decorated with embroidered images of birds and flowers.

A thick diamond choker sat on her neck, and she wore Louboutin shoes.

The musician, who is performing at the 2026 Oscars, looked dapper in a black-and-white Campillo suit and Christian Louboutin shoes. His suit included a matte-black jacket, a matching vest, and a white high-neck blouse.

He also sported multiple diamond and pearl accessories, including two brooches, earrings, and tassels hanging from his trouser waistband.

The statement piece, though, was his $91,600 white-gold Chopard L'Heure du Diamant watch.

The "Sinners" star stood out in red on the Oscars red carpet. Her strapless gown was made of satin and featured dramatic fabric swirls that created its 3D bodice.

Those same swirls also extended into a long train, which complemented the floor-length gown's lace-up skirt.

The "One Battle After Another" actor looked like a princess at the Oscars. She wore a sleeveless, lilac gown with a cowl neckline and a ruffled skirt. It was custom-made for her by Louis Vuitton.

Infiniti completed the look with a multicolored De Beers choker.

Byrne arrived on the red carpet in a strapless Dior mermaid gown. It was crafted from opaque black fabric and embellished with beaded floral designs. Her jewelry, a golden necklace shaped like a flower, matched.

She was nominated at this year's Oscars for best actress in a leading role after starring in "If I Had Legs I'd Kick You."