If you’re a Millennial, you definitely watched The Parent Trap growing up. It was a classic must-watch movie for us. And where our love for Lindsey Lohan began.
But now as we Millennials are a little older, we are finding ourselves dressing like Chessy. A lot. And how that even came to be considering Chessy was the nanny busy taking care of kids and probably didn’t think twice about her outfit.
But now, many of us are pulling out the Chessy outfit formula, and I’m guilty of this too. We all know about Chessy’s classic outfit, right? The olive green shorts, the t-shirt, and the oversized chambray shirt jacket over it all. I have found myself recreating this look over and over again.
At the time, Chessy’s style was trendy and fashionable. But we are DECADES past since The Parent Trap’s debut. So now that we’re in our 30s and 40s, it is time to transform Chessy’s outfits into something more modern, fresh and tailored to each of our own personal styles.
Revamping Chessy’s Outfits: How To Make Her Looks Work Today
Modernizing The Classics
Chessy’s outfit formula was very basic. There’s nothing fancy here. With that, we want to modernize the items. Each piece gets a little refresh to make it feel new.
But we also want to keep the color palette in mind. I think it’s the mix of the color palette and the pieces that make this feel quintessentially Chessy. Sure you can refresh the colors a bit, but I think the olive and denim is a must to keep consistent here!
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The Chambray Jacket
A few ways to do this is to update the chambray shirt jacket. Try something with a heavier weight to it as Chessy’s feels more like a shirt and not a jacket. And cuff the sleeves the J.Crew way so it feels more styled and not like you’re getting ready to work with kids.
You can also try a camp shirt too for something different. This is just a short sleeved jacket style. I love this one which would be a fun change of pace from our classic denim jackets.
Chessy did a classic roll a few times on her jacket which definitely feels more dated. The J.Crew cuff is to do one big fold-up of the entire sleeve up to where you want it to end. Then take the bottom of that large single fold and then fold it up once or twice to meet the end of the sleeve you’ve rolled. This leaves the top of the cuff out giving it more of a styled look to it.
The Olive Green Pants
With the cargo trend going strong right now, you can swap the olive green chino for this popular Gen Z trend. I love these cargo joggers so much and they’re a great update. You can also try a straight leg or wide leg cropped olive denim.
The Classic Tee
A classic tee really doesn’t need to be overly modernized much. But to try something new and trendy, I did a crochet crop top. This is a really great swap to try that feels modern and cool. And sure, maybe Chessy wouldn’t have shown a little midriff, but we’re now confident in this trend thanks to these tips.
Accessorizing For Impact
Chessy probably wasn’t too worried about her accessories considering she was caring for children as a nanny in The Parent Trap. But since we’re recreating this look for our everyday and not to be a nanny, we can add some fun accessories.
Try a cool chunky gold necklace, or hoop earrings. And don’t forget to add a great bag! Chessy was probably lugging around snacks, so her bag of choice may have been limited. Yours, however, are not.
Make It Your Own
Chessy’s style is Chessy’s. But we can all recreate it in our own way. Make this look fit your personal style by adding your own touch to it. For me, it was all about the cargo pant that I’m loving right now. Maybe you love pattern and prints and want to swap the olive pant for something with a print.
Either way, make the classic Chessy outfit your very own by adding your personal touch to it. A mix of classic pieces and on-trend swaps with your personal style will make the Chessy outfit formula feel new.
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