Weather 
Us has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!
We have been so fascinated with ’90s fashion this year, from chic styles inspired by Carolyn Bessette Kennedy to preppy outfits worn by Jennifer Aniston‘s character on Friends. And now that fall is almost here, we’re noticing that fashion people are reaching for a seasonal staple that might have you thinking about your favorite ’98 movie because of this one character. Okay, fine, we’ll tell you — it’s The Parent Trap, and yes, we’re talking about undeniably cool Chessy.
Lisa Ann Walter‘s character was the most understated fashion mogul, wearing loose denim shirts so much, they’re now synonymous with the effortless California vineyard style. It’s no wonder ‘It’ girls are channeling the beloved nanny with these comfy denim shirts. We’re pulling stylish options from Gap, Quince, Banana Republic, Abercrombie & Fitch, Amazon, Free People and more, starting at $24.
15 Denim Shirts to Get the Cool-Girl Fall Look
1. Our Favorite: A classic denim shirt is relaxed, soft and versatile, just like this popular long-sleeve pick on Amazon. It even has tabs underneath that allow you to roll up the sleeves on late-summer days and warm fall nights.
2. Editor-Approved: Levi’s jeans are a must-have in our fall closets, so you know this denim utility shirt will be equally top-notch. The large front pocket and loose silhouette embody that cool ’90s style.
3. Feminine Flair: Denim shirts don’t need to be rigid, just look at this ruffle-trim button-down shirt. The frilly details give it that soft touch that makes it stand out.
4. Quite the Charmer: Unlike most options on this list, this top-rated shirt has cute puffed sleeves that feel like your favorite blouse . . . in denim form.
5. Western Winner: Western-inspired shows have been popping up everywhere lately. It’s why this loose Wrangler top caught our eye, especially with the cowboy-like yoke stitching and front patch pockets.
6. Same But Different: If you love the aforementioned country style but want something a little more modern, go with this Levi’s Western shirt. It comes in tons of colors, including polished black.
7. Trending Find: Chocolate brown hues are going viral right now, so naturally we had to pick up this Gap denim shirt in the same rich color. It also comes in autumnal tan, bamboo green and more.
8. Laid-Back Luxe: Leave it to Quince to give the button-up shirt a fun twist. This popover shirt has buttons that line only a quarter of the way down to give it visual interest when worn solo or layered.
9. Everyday Ease: Want to get the classic denim shirt look without sweating? This short-sleeve option gets the job done right. It’s structured and has all the quintessential details that make a solid denim shirt.
10. No Brainer: This denim tank top from Abercrombie & Fitch gives off rich mom vibes due to the high neckline, straight fit and accented band at the hem. The low back is the icing on the cake.
11. CEO Energy: Just because denim is on the casual side doesn’t mean you can’t style it for the office. This upscale Banana Republic quarter-sleeve top is proof.
12. Silhouette Saver: Not into the oversized look? This slim-fitting denim shirt accentuates your curves by slightly cinching at the waist. It’s so flattering!
13. Closet Hero: Stop stealing from your boo and get this oversized boyfriend shirt instead! It’s perfectly loose, long and classy, just like Chessy’s look.
14. Boho Babe: Americana style meets bohemian-chic with this Free People top. The denim style has a fun mix-matched button front, pleats and a peplum-like bottom.
15. Expensive-Looking: We adore this Anthropologie denim shirt that has a low neckline, ruffled details and a notched hem that gives it an edge.
