Natalie Portman Flaunts Her Legs and Shoe Game on the Good Sex Set: From Oxfords to Proenza Loafers

Natalie Portman is stepping into style once again—this time on the set of Good Sex, her upcoming romantic comedy with Lena Dunham.

Judging by her standout footwear choices, this film isn’t just promising romance and laughs—it’s delivering serious shoe moments, too.

Natalie Portman parades her chic shoe game—including Oxfords, Mary Janes, and loafers—and versatile outfits, from tailored shorts to a preppy mini-skirt and a sophisticated shirt dress, on the set of her upcoming movie, “Good Sex” (Credit: Jose Perez / INSTARimages)

In the film, Portman plays Ally, a 40-year-old couples therapist reentering the dating scene after the end of a decade-long relationship. She becomes romantically involved with two men: a 20-something Brooklyn hipster and a more conventional, successful man in his 50s.

As her love life becomes more complicated, Ally tries to keep the two men apart while figuring out what she truly wants before she risks losing them both.

Mark Ruffalo and Tucker Pillsbury star as the two love interests. Good Sex is written, directed, and produced by Lena Dunham.

Sharp & Street-Smart: Natalie Portman’s Blazer, Shorts, and Polished Oxfords

Portman was pictured on the streets of New York, effortlessly serving cool-girl elegance in a monochromatic black and gray ensemble that combined casual and tailored elements.

Natalie wore a black top with a scalloped neckline that added a hint of femininity, paired with a pair of black shorts featuring raw, frayed hems that showcased her slim legs and gave the look an off-duty, cool vibe. Throwing a gray blazer over the laid-back combination, Natalie instantly elevated her outfit with a tailored edge and a borrowed-from-the-boys finish.

This city-ready ensemble pays homage to menswear while remaining contemporary and fashion-forward.

Natalie Portman exudes cool-girl elegance in black shorts with frayed hems and an oversized gray blazer, expertly paired with sleek black Oxfords (Credit: Roger Wong / INSTARimages)

Portman accessorized the look with black Ray-Ban cat-eye sunglasses and a black cord necklace adorned with a gemstone pendant. Adding a touch of sparkle, she wore several statement rings in black and white gold, each embellished with diamonds for a refined yet striking finish.

With a coffee in one hand and her mobile phone in the other, Natalie carried her other essentials in a black Jacquemus shoulder bag.

She completed her modern monochromatic ensemble with black Oxfords, enhancing the outfit’s sleek, androgynous edge. These shiny patent leather shoes feature the classic Oxford DNA, with lacing, almond toes, and about an inch of stacked heels.

Natalie Portman teams her casual shorts with black leather Oxford shoes, enhancing the outfit’s sleek, androgynous edge (Credit: Roger Wong / INSTARimages)

Portman’s sleek patent leather Oxfords perfectly encapsulate the enduring appeal of this classic style—equal parts polished, practical, and fashion-forward. She’s not the only star stepping out in this timeless footwear trend.

Parisian Power Look: Alaïa Poplin Dress & Sleek Mary Jane Pumps

Earlier in the day, Natalie Portman was spotted in a more polished and sophisticated ensemble while filming on the set of Good Sex. She channeled Parisian chic in a tailored gray skater dress by Alaïa, a high-fashion choice with a luxury price tag of $3,010.

Crafted in Italy from structured double poplin, this preppy dress perfectly blends elegance with a modern edge. It features a sharp, pointed collar, short sleeves with buttoned cuffs, and two flap chest pockets that add a utilitarian touch.

The fit-and-flare silhouette, cinched at the waist, accentuates Portman’s figure before flaring into a crisp A-line mini skirt, showcasing her slim legs. It also has strategically placed exposed seams that create the illusion of a slimmer frame.

This dress creates a flattering, feminine silhouette that mirrors the brand’s signature architectural appeal. It seamlessly balances classic tailoring with a youthful flair, highlighting Portman’s styling prowess!

Natalie Portman stuns in a chic gray Alaïa poplin mini dress, featuring a pointed collar, practical chest pockets, and elegant short sleeves (Credit: Jose Perez / INSTARimages)

Natalie hid her eyes beneath a pair of brown tortoiseshell cat-eye sunnies, adding a retro-chic touch to her preppy ensemble while keeping things effortlessly cool. She wore the Dior Eyewear DiorSignature B7I sunglasses, $590 at Mytheresa.

Her essentials were kept in the Jacquemus “Le Coeur” bag, a heart-shaped bag crafted from perforated white leather and finished with a long cross-body strap. This complemented her white Mary Jane pumps that gave off a refined, slightly retro-modern vibe.

These pumps have upturned pointed toes that lend a sleek, sophisticated twist to the traditionally youthful Mary Jane silhouette. They’re finished with a strap across the foot and high heels to boost Natalie’s 5’3” height.

Natalie Portman elegantly pairs her gray mini dress with sophisticated white pointed-toe Mary Jane pumps, highlighting a key footwear trend (Credit: Jose Perez / INSTARimages)

Portman’s pointed-toe Mary Jane pumps put a modern twist on the classic silhouette, blending retro charm with contemporary sophistication. She’s in stylish company—countless celebrities have turned to Mary Janes to deliver everything from polished elegance to playful edge.

Preppy Chic Revival: Prada Blouse, Zara Mini & Sculptural Loafers

This is probably my favorite look from Natalie Portman from the Good Sex set in New York City. She wore a cream-colored blouse by Prada that perfectly blended elegance and vintage charm. It was adorned with a black pussybow and decorative black chest pockets with gold button accents, creating a sense of refined, old-school sophistication.

The blouse’s delicate pleated sable fabric, structured collar, and three-quarter sleeves enhanced its prim, modest charm. Portman balanced the softness of the top with a structured high-waisted black Zara mini skirt. It struck a balance between polished and playful thanks to its clean and tailored silhouette, which added a flirty, youthful contrast to the ensemble.

I’m sure Blair Waldorf would approve of this preppy-chic moment from Portman!

Natalie Portman channels her inner Blair Waldorf in an ivory Prada pleated blouse with a black pussy bow and chest pockets and a black Zara mini skirt (Credit: Jose Perez / INSTARimages)

Portman’s accessories were thoughtfully curated, opting for black and gold to reflect the polished colors of her ensemble. She wore the whimsical yet elegant “Les Boucles” Rond Carré earrings by Jacquemus, $320 at Mytheresa. Made from pleated brass in Italy, they included two mismatched geometric shapes—a square and a circle—that gave her otherwise classic look a modern, sculptural edge.

Natalie also wore a few gold rings and carried the “Le Petit Calino” Mini Leather Tote Bag by Jacquemus. Made of black nappa leather, this bag features a curved shape with an integrated gold-tone logo-engraved ring handle, complementing the rest of her accessories. It’s now on sale for $1,036 (from $1,296) at Mytheresa.

Wearing her brunette hair down, Natalie hid her eyes behind black cat-eye sunglasses by Oliver Peoples. The “Avelin” sunnies are made from glossy black acetate and have glare-reducing polarized lenses. They’re available for $580 at Net-a-Porter.

Natalie Portman styles her preppy ensemble with Jacquemus mismatched Les Boucles earrings and Le Petit Calino bag with a gold-tone ring handle (Credit: Jose Perez / INSTARimages)

Portman completed her ensemble with timeless black loafers by Proenza Schouler, which perfectly complemented the preppy vibes of her look while lending an air of carefree sophistication.

They are crafted in Italy from black goat leather with lamb leather lining, featuring square toes and a seamless, almost sculptural silhouette that gives them a sleek, minimalist appearance. The notched opening at the vamps gives the classic loafer silhouette visual interest and a modern twist.

They also have flat soles, rear pull tabs, and an elasticated back for a snug fit, adding comfort without compromising style.

Natalie Portman completes her outfit’s preppy vibe with black loafers by Proenza Schouler featuring notched side openings (Credit: Jose Perez / INSTARimages)

Portman’s Proenza Schouler loafers add a touch of sculptural minimalism to her prim ensemble—proof that loafers can be both elegant and edgy. From heeled styles to classic penny loafers, these shoes remain a staple in the wardrobes of celebrities and fashion insiders alike.