3 Lindsay Lohan Outfits That Give Hallie Parker (And 3 That Are So Annie James)

Few actors can say they played two characters in one movie, but one of those precious few is Lindsay Lohan. Most of us can't remember how many times we watched the 1998 remake of "The Parent Trap," where Lohan starred as the two mischievous twins Hallie and Annie Parker. Lohan was so great at playing the California- and London-raised 11-year-old sisters that many of us thought she actually had a twin sister for years.

Lohan has created a name for herself in several other cult classics, including "Freaky Friday," "Mean Girls," and "Confessions of a Teenage Drama Queen." And to be honest, she is and will always be a moment. As much as we love her in her later projects, we can't help but notice times when her looks, whether on the red carpet, during media tours, or on social media, remind us of the Parker twins.

Like a photo she shared on her Instagram, in which she's donning a cream-colored silk slip gown with a trench coat of the same color hanging off her shoulders. This is something we can see Annie sporting, especially with how much she learned from her fashion designer mother Liz Parker.

In an interview with Vogue, Lindsay Lohan admitted she liked clothes that were "effortless and chic, but comfort is key." She added that her red carpet looks had to be authentic to her, but she is willing to go outside of her comfort zone. Lohan shared a photo on Instagram of herself wearing a gorgeous black sequin turtleneck gown with black shades, which she wore to Balenciaga's show during Paris Fashion Week. This look could be a bit out of the comfort zone for Hallie, who has more of a laid-back style. But the bold look could also be right up Hallie's alley thanks to her fearlessness ... except when it came to her dad possibly marrying Meredith Blake.

In another photo Lindsay Lohan posted to Instagram, she posed in a black skirt set during her appearance on "The Tonight Show Starring Jimmy Fallon," to talk about "Freakier Friday." The set from the Zuhair Murad Ready-to-Wear Resort 2025 collection featured an above-the-knee skirt, and long-sleeved top that featured silver jeweled detailing. She paired it with sheer black tights and black pumps. In this case, we could totally see Annie wearing this outfit to channel her feminine side while also taking a leaf from her sister's book with a darker look. But we have a feeling that the silver jewelry detailing is bougie enough for the daughter of a wedding dress designer.

In July 2022, Lindsay Lohan shared a shot of herself in the Turkish Riviera looking out at a breathtaking view at a luxurious resort. In the photo, Lohan's long signature red hair cascades down her back in a floral sundress that features a large back cutout and spaghetti straps. This would definitely be a look that Annie would wear while visiting her father at his California vineyard, or even just enjoying the scenery on a solo vacation. 

Lindsay Lohan looks great in yellow, proving such as she sported a bright yellow bomber jacket with beaded embroidery details in the Dubai desert. In the Instagram post, she paired the jacket with a white button-up top with a large collar and white high-waisted pants. The look was giving grown-up Hallie, who would have gone crazy over the statement-making jacket against the laid-back business casual look. We can just imagine her wearing this outfit in a meeting with wine distributors at her family's vineyard.

In a partnership with Planet Fitness, Lindsay Lohan wore a short-sleeved denim jumpsuit sitting in what looks like a garage. In the Instagram photo, Lohan appeared to be channeling her inner Hallie, who would have been in heaven getting her hands dirty and would look great doing it. The look also taps into the simplicity of Hallie's outfits throughout the film, but simple still means chic, because she was a style icon taking after her wedding dress designer mother.