Bailee Madison’s Best Fashion Moments: From Sheer Stockings to Strappy Sandals

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Bailee Madison began her career as a baby in an Office Depot commercial and has since become a red-carpet fashion icon. From her major film debut in Lonely Hearts (2006) to stunning footwear choices at events like the Star Wars: The Rise of Skywalker premiere, Bailee consistently dazzles with her sophisticated style.

Bailee Madison and Blake Richardson out for a dinner date at Craig’sBailee Madison and Blake Richardson out for a dinner date at Craig’s in West Hollywood, California, on January 10, 2020 (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

In December 2019, she flaunted her legs in black stockings at the premiere of Star Wars: The Rise of Skywalker.

Bailee Madison exudes chic sophistication in a structured gray mini blazer dress paired with sheer black stockings and pointed-toe pumps at the Star Wars: The Rise of Skywalker premiereBailee Madison exudes chic sophistication in a structured gray mini blazer dress paired with sheer black stockings and pointed-toe pumps at the Star Wars: The Rise of Skywalker premiere in London, England, on December 18, 2019 (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

In January 2019, Bailee Madison flaunted her hot legs at the 2019 LA Art Show Opening Night Gala.

Bailee Madison stuns in a chic, patterned mini dress paired with classic velvet pumps at the 2019 LA Art Show Opening Night GalaBailee Madison stuns in a chic, patterned mini dress paired with classic velvet pumps at the 2019 LA Art Show Opening Night Gala at the Los Angeles Convention Center on January 23, 2019 (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

Bailee Madison revealed toe cleavage in pointy-toe high-heeled pumps.

Bailee Madison's toe cleavage in pointy-toe stiletto heelsBailee Madison’s toe cleavage in pointy-toe stiletto heels (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

Earlier the same month, Bailee displayed her bare legs in a Ponza silk-chiffon midi dress from Joseph Altuzarra’s Resort 2019 collection. Her good friend Peyton List joined her at the InStyle And Warner Bros. Golden Globes After Party.

Bailee Madison and Peyton List flaunt their legs at the InStyle And Warner Bros. Golden Globes After Party held at The Beverly Hilton Hotel in Beverly Hills, California, on January 6, 2019Bailee Madison and Peyton List flaunt their legs at the InStyle And Warner Bros. Golden Globes After Party held at The Beverly Hilton Hotel in Beverly Hills, California, on January 6, 2019 (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

Bailee’s blue silk-chiffon midi dress from Altuzarra is crafted in Italy for a slim fit with a flattering V-neckline and a slender pencil skirt that is slit open on one side and printed with an idyllic coastal scene – inspired by the equally charming settings of André Aciman’s novel Call Me By Your Name.

While Peyton opted for a revealing Valentino dress, both ladies highlighted their feet in strappy, barely-there sandals.

Bailee Madison and Peyton List flaunt their pedicures in glamorous metallic stiletto sandals at the 2019 InStyle and Warner Bros. Golden Globes After PartyBailee Madison and Peyton List flaunt their pedicures in glamorous metallic stiletto sandals at the 2019 InStyle and Warner Bros. Golden Globes After Party (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

Bailee Madison also showed off her feet in ‘Snake’ crystal-embellished metallic leather sandals from René Caovilla at the 2018 Radio Disney Music Awards in Los Angeles.

Bailee Madison looks radiant in a plaid spaghetti strap dress, complemented by bold red lipstick and soft waves at the 2018 Radio Disney Music AwardsBailee Madison looks radiant in a plaid spaghetti strap dress, complemented by bold red lipstick and soft waves at the 2018 Radio Disney Music Awards in Los Angeles on June 22, 2018 (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

The then-18-year-old American ‘Good Witch’ actress paired her shoes with a gorgeous plaid Prabal Gurung Pre-Fall 2018 Collection dress.

Bailee Madison accessorized with a variety of rings from Monica VinaderBailee Madison accessorized with a variety of rings from Monica Vinader (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

Cut from a draped fabric in all-over plaid, it features a cascading ruffle down the side, highlighting the feminine form. She accessorized with a variety of rings from Monica Vinader.

Bailee Madison's Prabal Gurung dress features a cascading ruffle down the side, highlighting the feminine formBailee Madison’s Prabal Gurung dress features a cascading ruffle down the side, highlighting the feminine form (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)

René Caovilla has used the same expert craftsmanship methods since its launch in the ’30s. These silver leather ‘Snake’ sandals have shimmering crystal-embellished straps that coil around your ankle. They’re lightly structured, so they won’t slouch down as you walk.

Rihanna wore a custom-made pair of René Caovilla’s ‘Snake’ sandals at her Fenty Beauty launch in London.

Bailee Madison showcases her flawless pedicure in René Caovilla’s ‘Snake’ crystal-embellished metallic leather sandalsBailee Madison showcases her flawless pedicure in René Caovilla’s ‘Snake’ crystal-embellished metallic leather sandals (Credit: WENN / Apega / FayesVision / Adriana M. Barraza / Instar)