In My Chessy Era: Outfits Inspired by The Parent Trap

Our recent trip to London was truly magical and it brought back a lot of my favorite childhood memories, especially those I associated with the iconic movie (and one of my personal favorites), The Parent Trap. Seeing the exterior facade of the London home IRL where they filmed scenes in the movie unlocked a core memory that I’ll never forget! I was very emotional being there in person and it made me realize how influential this movie was in shaping my childhood. I had the original movie soundtrack CD that I listened to constantly, begged my mom for my very own “Cuppy” that the Disney Store was selling, and even started teaching myself how to play poker 😂

This experience reignited my love for the movie even more and I was inspired to recreate some of the movie's iconic outfits. I couldn’t help but kick things off with one of my favorite characters from the movie - the charismatic and beloved Chessy. I took Chessy's iconic style (oversized denim shirts, khaki pants, and loafers) and picked out key pieces that would recreate the same vibe in a more trendy outfit - I’m SO happy with the result!

This oversized denim shacket was the starting point that I built my outfit around - I mean, doesn’t it just scream Chessy?! I love it so much and it’s a super soft denim which I love; it’s not stiff like some other denim jackets I’ve had. I wanted to keep the color palette of the outfit more toned down and neutral since Chessy’s style is not colorful or vibrant. I loved the idea of pairing the shacket with this pair of ivory “dad shorts” which give a more relaxed vibe. I also thought this sage green bodysuit would be perfect since it’s a similar color to the green khaki tones she wears a couple times throughout the movie. I wanted to stick with a sporty chic aesthetic so I opted for my New Balance 327 sneakers to complete the outfit. They are so comfortable and I love that they go with pretty much anything!

I can’t wait to hear your thoughts on this look - do you think I nailed it or would you do something different? I’m so excited to continue my fashion journey through the film's iconic outfits, so please let me know which character’s style I should recreate next!