Are You a Meredith or a Chessy? Fall Pieces Based on ‘The Parent Trap’

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Of the countless fall fashion trends this year, two are standing out as my favorites: 1) Classic prep (with a touch of sporty-chic) and 2) The relaxed, cool girl aesthetic. As I have been saving outfit inspo on Pinterest and online shopping in these two styles, I’ve noticed that there is something that already ties them together—the movie The Parent Trap. Meredith Blake is a classic-prep-meets-sporty-chic icon, and Chessy basically invented the relaxed cool girl. 

The return of ’90s fashion has been reigning supreme for the past few years, so it’s no surprise that these two cultural icons have also become major style inspirations for a lot of people. Their styles work especially well for the fall season, given Meredith’s athleisure and workwear-inspired pieces and Chessy’s expert layering and oversized silhouettes. So whether you’re feeling more like a Meredith or a Chessy this fall, we’ve got you covered.

 

If you’re more of a Meredith Blake…

Meredith has two style moods in the movie: workwear-inspired preppy and sporty-chic athleisure. She’s also always in black, white, and/or gray, which is perfect for all of the neutral-loving gals out there. Most importantly, whether she’s wearing a workout set (like in the famous camping scene), or a shift dress, she is always impeccably dressed and put-together. If you’re looking to step up your style game and look incredibly chic all the time, channeling your inner Meredith Blake is perfect for you.

J.Crew

Stretch Crepe Sheath Dress

3 colors available

Abercrombie & Fitch

Cropped Blazer

3 colors available

Abercrombie & Fitch

Wrapped Mini Skirt

3 colors available

Girlfriend Collective

Pleated Club Skort

4 colors available

1.STATE

Pleated Trousers

2 colors available

Gigi C Bikinis

Reina Tank

Madewell

Field Knit Sneakers

5 colors available

J.Crew

Button-Back Linen Shift Dress

4 colors available

Abercrombie & Fitch

Notch-Neck Midi Dress

4 colors available

Everlane

The Cotton-Merino Front-Tie Top

4 colors available

Girlfriend Collective

Cami Unitard

6 colors available

Everlane

The Rib Knit Top

2 colors available

J.Crew

Slingback Heels

3 colors available

Abercrombie & Fitch

Tweed Set Top

3 colors available

Abercrombie & Fitch

Tweed Mini Skort

3 colors available

Longchamp

Large Le Pilage Tote

2 colors available

Abercrombie & Fitch

Vegan Leather '90s Pants

4 colors available

 

If you’re more of a Chessy…

Chessy’s style is exactly what I’m striving for this fall. The mix of classic silhouettes (i.e. straight-leg denim and oversized button-ups), effortless layering, and an earth-toned color palette make an ideal foundation for a fall capsule wardrobe. Add in some chunky knits and easy-to-wear shoes and you can live out your Pinterest girl dreams.

 

J.Crew

Chambray Shirt

2 colors available

J.Crew

Cable-Knit Stretch Cardigan

2 colors available

Madewell

Softfade Cotton Crop Tee

6 colors available

Birkenstock

Boston Soft Footbed Clog

3 colors available

Everlane

The Cozy-Stretch Pullover

2 colors available

Abercrombie & Fitch

Curve Love Ultra High Rise '90s Straight Jean

18 colors available

Abercrombie & Fitch

Cozy Shirt Jacket

5 colors available

Abercrombie & Fitch

Poplin Button Up

18 colors available

Abercrombie & Fitch

'90s Relaxed Jean

9 colors available

Veja

V-12 Mesh Sneakers

2 colors available

Madewell

Bouclé Sweater Vest

2 colors available

Free People

Rosebery Leather Belt

3 colors available

Everlane

The Alpaca Waffle-Stitch Polo

4 colors available

Everlane

The Relaxed Chino

6 colors available

Madewell

The Oversized Trucker Jacket

3 colors available

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