I Introduced My Boyfriend's Mom to Madewell—9 Fall Finds We're Obsessing Over
Although my boyfriend's mom and I have wildly different clothing styles, there's one thing we can now agree on when it comes to fall fashion: Madewell.
For the last seven years, she's constantly been complimenting my edgy, trend-forward style and asking to go shopping with me and style her—something I'm practically an expert at now. To be honest, though, at 66 and 24 years old, she and I don't have too many items in the center of our fashion Venn diagram. After stumbling upon a Madewell store during a recent family vacation, though, I was shocked to find the number of things she and I both fell in love with.
Although the brand's trendy offerings make it a younger, "cooler" retailer when compared to big-sister brand J.Crew, Madewell's fall lineup of chic knits, sharp suiting, and sleek denim makes it a favorite for anyone who likes great clothes regardless of how old they are. If that isn't a testament to how good Madewell is right now, I don't know what is.
Below, shop the nine pieces my boyfriend's mom and I swooned over when we went into Madewell. Trust us, you'll want to pick these up for yourself before they sell out.
After seeing this cardigan IRL, we both fell in love with how soft it was in person—a requirement when you're trying to live out your cozy fantasies this fall. Opt for a pair of straight-leg jeans or tailored pants for a chic, timeless look no matter your age.
Yep, the TikTok-viral Harlow wide-leg pants are just as good IRL as they are online. Despite being vastly different heights and sizes, my boyfriend's mom and I were able to see how great these pants looked on both of us thanks to their slightly slouchy (but not too oversize) fit. Win-win.
If you're looking to step up your sweater game this fall without leaning into the same basic neutrals every other brand is offering, look no further. While I love a classic white, black, or tan sweater, this subdued chartreuse color is doing it for me, and I knew I had to get my boyfriend's mom's take on it. Her response? A glowing review when I showed it to her. If you're nervous about wearing a bright-colored sweater, opt for a classic denim wash and a pair of white sneakers to tone down the rest of the look.
After Madewell's PR manager, Annie, put me on to these jeans earlier this year, I haven't been able to put them down. Naturally, I had to get my boyfriend's mom on the bandwagon too with this "buy once, wear forever" style that's both universally flattering and seemingly timeless, meaning it'll last for years to come.
While my boyfriend's mom and I usually avoid heels, we can stand behind this adorable pair. Due to its sleek leather silhouette and ultra-mini kitten heel that's easy to walk in, we instantly reached for this pair when we saw it. Not only is it a luxe-looking style, but thanks to its slim, low profile, it's extra comfortable.
The perfect way to spice up any fall outfit? Throwing a crisp shacket on top of any outfit of choice. If you're looking for something that'll keep you warm without being too dressy or stuffy, my boyfriend's mom and I instantly had to get this shacket when we saw it in-store. While the neutral blue option looks so chic paired with jeans, the burnt-orange option is perfect for crisp fall days.
This pair of jeans gets a solid 10/10 from both of us. Regardless of your preference of skinny, wide, or straight-leg jeans, this retro-inspired cut hugs in all the right places and elongates the leg, something my boyfriend's petite mom could stand behind. As a taller person myself 5'9", these jeans were long enough to cover the top of my ankles while maintaining a straight, flattering cut throughout my thigh. It's safe to say we're both obsessed.
While there's nothing better than a crisp, white button-down shirt to go with every outfit, my boyfriend's mom and I agreed there was something special about this chic statement shirt.Say goodbye to boring 'fits: We love how it looks styled above with mid-wash denim jeans and a simple leather belt. Not only does it feel cool enough to go out and run errands in, but the simple switch-up with colored stripes leads the style to feel extra fun.
My boyfriend's mom and I love Breton stripes just as much as the French do. This timeless style goes well with nearly everything in our closets, from our favorite pair of jeans to simple column maxi skirts for dressier occasions. She and I agree the less we have to think about outfits, the better, and frankly, it doesn't get easier than throwing on this adorable striped shirt and heading out the door.
Shop more Madewell items we love:
Ana Escalante is an award-winning journalist and Gen Z editor whose work ranges from dissecting size inclusivity at fashion week to discussing how American Girl Doll meme accounts are the the answer to society's collective spiral. She's covered it all: Queen Elizabeth II's corgis, Roe v. Wade frontline protests, and the emergence of jorts (or jean shorts for the uninitiated). At Who What Wear, Ana is responsible for delivering smart, insightful, personality-driven shopping guides and trend features for a digital-first generation.Before joining Who What Wear, Ana was Glamour magazine's editorial assistant, where she focused on daily news and special packages, including leading the brand's 2022 Met Gala coverage. For more than half a decade, she has covered style, beauty, and digital culture for publications such as Paper magazine, Harper's Bazaar, Vogue Japan, and Allure, among others. Ana has been called a rising star in media by publications such as Nylon and Teen Vogue. (Her mother, meanwhile, calls her "the coolest person" she knows.)
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