Kaia Gerber Wore the Most On-Trend Madewell Item With Jeans

In case you're in need of some fall outfit inspiration (there has been a bit of a chill in the air on the East Coast this week), look no further than outfit master Kaia Gerber. While out in Malibu over the weekend, Gerber wore an outfit formula that she often relies on: a blazer, crop top, loose-fit jeans, and sneakers. You truly can't go wrong with this combination, especially in the coming early fall months (and feel free to swap the crop top out for a T-shirt).
Gerber has truly mastered the high-low mix, frequently pairing designer items with affordable finds, and that's exactly what she did with this outfit, which she incorporated a $168 Madewell blazer into. The oversize checked blazer perfectly nails fall's bourgeoisie trend, which includes refined pieces like suiting and heritage prints that can be worn every day. It truly doesn't get more bourgeoisie than her double-breasted blazer in timeless shades of brown.
Keep scrolling to see how Gerber styled the trend, and shop her look.
On Kaia Gerber: Madewell Caldwell Plaid Double-Breasted Blazer ($168); Stella McCartney Mini Stella Logo Camera Bag ($517); Converse Chuck Taylor High Top Sneakers ($55); Palm Angels x Moncler sunglasses
Shop the Look
Shop More Madewell Items to Wear With the Blazer
Next up, 11 fall trends that are kind of just basics.

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall Closet
Stylish sweaters and suedes ahead.
-
It's Here: The It-Girl Sweater Trend of Fall 2025
Kaia Gerber has solidified it.
-
Madewell's Labor Day Sale Is Full of Chic Elevated Basics—Up to 70% Off
Through September 2.
-
If You're Going to Wear Leggings in 2025, Please Only Wear Them Like This, This, and This
Courtesy of our favorite stylish celebrities.
-
36 Zara, Madewell, and H&M Essentials I'm Buying to Look Expensive This Fall
Elevated and easy.
-
These Are the Only Labor Day Weekend Sales That Matter—Shop the Best Deals Thanks to Nordstrom, Madewell, J.Crew, and More
Save big on fall staples.
-
Sarah Burton Flipped the Script for Her First Givenchy Campaign—See All the Photos
Starring Kaia Gerber, Eva Herzigova, Adut Akech, and more.
-
I Accidentally Started a Capsule Wardrobe When I Added These COS, Madewell, and J.Crew Items Into My Closet
And I got rid of all the pieces that couldn't compete.