In August 2013, Oprah landed what many called the interview of the year—sitting down with Lindsay Lohan just days after the actress completed her 90-day court-ordered rehab. The buzz was already building thanks to a 15-second teaser released ahead of the full interview, part of Oprah’s Next Chapter.
In the preview clip, Oprah didn’t hold back—diving straight into the tough questions fans and critics had long been waiting for. One standout moment? Oprah directly asked Lindsay how it felt to be labeled the poster child for “a child star gone wrong.”
But while the world braced for her answers, fashion watchers were already analyzing Lindsay’s striking look: a high-necked, cap-sleeved, fit-and-flare knit dress in bold orange—paired with black-and-white polka-dot pumps by Oscar de la Renta and a sleek high ponytail. The outfit was eye-catching, calculated, and possibly symbolic.
Was this a fresh start in fashion form? Or a strategic move to shape public perception? Watch the teaser and decide for yourself:
Lindsay’s Bold Outfit: Playful or Strategic?
None of Lindsay’s responses were included in the preview, but she was shown wearing a bright orange fit-and-flare knit dress and black-and-white polka-dot pumps on her feet.
Lindsay Lohan’s candid interview on Oprah Winfrey’s show, “Oprah’s Next Chapter,” marked Lohan’s first comprehensive interview following her release from her sixth round of rehab (Credit: Oprah’s Next Chapter)
Perhaps her playful and perky outfit choice was her way of lightening up the mood a little? Or maybe it was her way of appearing happy, especially since she just exited rehab?
Lindsay Lohan donned a vibrant orange Alessandro Dell’Acqua dress paired with Oscar de la Renta’s polka-dot pumps (Credit: Oprah’s Next Chapter)
We know Lindsay has a penchant for putting on a particular image when she has to attend a court hearing, and it looks like this right-out-of-rehab interview with Oprah is no different.
Lindsay Lohan wore a high-necked, cap-sleeved, fit-and-flare dress in a bright orange color that some have described as “prison orange” (Credit: Oprah Winfrey Network)
Is Orange the New… Innocence?
Lindsay laid the demureness on thick in her choice of a high-necked, cap-sleeved, fit-and-flare dress. Black-and-white polka-dotted pumps lent an air of playful innocence, and a high ponytail kept her look neat and clean.
However, Lindsay seemed to have overlooked one detail in her prim and proper attire: her choice of dress color.
Not a few websites describe it as “prison orange.” When the dress was still on the hanger, Lindsay Lohan may have thought it looked more like a cheery, bright yellow-orange.
Do you think Lindsay Lohan’s No. 21 orange fit-and-flare knit dress was a good choice for her Oprah interview?
The conservative outfit with black-and-white polka-dotted pumps and a high ponytail was likely a way for Lindsay to project an image of sobriety and maturity (Credit: Oprah Winfrey Network)
Lohan’s Style Strategy: Dressing to Shape Perception
We know Lindsay likes to dress demurely to prove her innocence. We also know that polka-dot pumps aren’t her style; Lindsay prefers her shoes sexy, fierce, and super high:
Lindsay Lohan chose a bold, cleavage-revealing Dolce & Gabbana dress for the premiere of ‘Scary Movie 5’ in Los Angeles, California, on April 11, 2013 (Credit: Daniel Tanner / WENN / FayesVision / Visual)
Lindsay Lohan displays her feet in black Christian Louboutin “Coussin” animal-print booties (Credit: Daniel Tanner / WENN / FayesVision / Visual)
On January 4, 2013, Lindsay Lohan was spotted at China Tang restaurant in London, elegantly sporting red sole Christian Louboutin’s “Bandita” boots (Credit: Daniel Tanner / WENN / FayesVision / Visual)
On December 30, 2012, Lindsay Lohan graced The Dorchester in London, England, donning chic Christian Louboutin “Aeronotoc” booties (Credit: Daniel Tanner / WENN / FayesVision / Visual)
From Sexy to Subtle: A Look at Lindsay’s Shoe Evolution
Lindsay’s polka-dot pumps are Oscar de la Renta’s “Mimi” pumps from the designer’s Pre-Fall 2013 collection.
Oscar de la Renta “Mimi” Pumps, $625
While Lindsay’s polka-dot pumps made a subtle yet striking statement during her Oprah interview, she’s far from the only star to embrace this playful print. From red carpet glam to bold street style, polka dot heels have strutted their way into the wardrobes of many fashion-forward celebrities. Here are a few standout moments:
Stepping Out in Style: Celebrities Who Love Polka Dot Heels
Polka dot heels have made a playful yet sophisticated statement in fashion, with numerous celebrities showcasing this timeless pattern. Here are some standout moments featuring polka-dot footwear:
Janelle Monáe’s Daring Met Gala Look
- Event: 2019 Met Gala
- Outfit: Janelle Monáe paid homage to Pablo Picasso in a custom surrealist ensemble by Christian Siriano. The ensemble featured an eye motif with feathered eyelashes that blinked.
- Footwear: She completed her avant-garde look with Christian Louboutin’s “Bibariellita” polka-dot red-sole sandals, which added a whimsical touch to her dramatic outfit.
- More Details: Janelle Monáe’s Met Gala statement with polka dot heels
Alexa Chung’s Chic Summer Party Ensemble
- Event: 2018 Serpentine Gallery Summer Party
- Outfit: Alexa Chung donned a lacy Chanel Fall 2018 dress featuring a satin bow detail around the waist, exuding elegance and charm.
- Footwear: She paired her dress with Christian Louboutin’s “Miss Daisy” polka dot-print suede mules, which perfectly complement her sophisticated look.
- More Details: Alexa Chung’s polka dot mules at the Serpentine Gallery Summer Party
Olivia Culpo’s Bold National Polka Dot Day Outfit
- Event: Minnie Mouse Rocks the Dots Art and Fashion Exhibit
- Outfit: Olivia Culpo celebrated National Polka Dot Day in a daring low-cut Givenchy blazer and matching trousers adorned with tiny white cross prints.
- Footwear: She completed her ensemble with Olgana’s “La Garconne” pumps, adding a touch of elegance to her bold look.
- More Details: Olivia Culpo’s polka dot-inspired fashion statement
Kate Moss’s Edgy Paris Fashion Week Appearance
- Event: Saint Laurent Show at Paris Fashion Week
- Outfit: Kate Moss made a daring entrance in a sheer polka dot blouse paired with a black velvet blazer and cigarette pants, showcasing her signature edgy style.
- Footwear: She elevated her look with pointed mules, adding a modern twist to her ensemble.
- More Details: Kate Moss’s bold polka dot fashion at Paris Fashion Week
Marion Cotillard’s Elegant Red Carpet Choice
- Event: Palm Springs International Film Festival
- Outfit: Marion Cotillard exuded sophistication in a one-shoulder Elie Saab dress, perfectly balancing classic and contemporary elements.
- Footwear: She complemented her dress with Christian Dior gladiator sandals featuring intricate lattice-style straps adorned with metallic embellishments, adding a touch of glamour to her look.
- More Details: Marion Cotillard’s chic ensemble at the Palm Springs Film Festival
These moments highlight the versatility and timeless appeal of polka dot heels in celebrity fashion, seamlessly blending playful patterns with high-end style.