My Mom and I Went Shopping at Madewell for the Insiders Event—These Are the Chicest Finds

As I discuss regularly, my mom and I love shopping together. We’re both in the process of building out our spring and summer wardrobes and decided to bop into one of our favorite stores, Madewell, in Madison, Wisconsin, at Hilldale Mall, to see what’s new. Side note: We chose this specific time because the Insiders Event is happening through March 24 (aka, 25% off for Madewell Insiders).
The new Madewell drop is unsurprisingly filled with stellar finds. We both gravitate toward Madewell denim, and I picked up a barrel-leg pair, while she opted for a dark-wash straight-leg silhouette. The accessories are next-level, and we both couldn’t resist the woven leather totes in navy and brown. (That’s me above with my tote and a Madewell jacket and hat.) Beyond. Keep scrolling to shop the chicest items we spotted both in-store and while browsing online.
Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
Suddenly, This "Glum" Hue Is 2025's Hottest Makeup Trend—Doechii and Julia Fox Are Proof
Forget what you know about pastels for spring.
By Alyssa Brascia
-
I Spent the Afternoon Scrolling Through Saks Off 5th—Wow, These Discounted Shoes and Accessories Are Very Chic
Sunglasses, bags, sandals, and more.
By Bobby Schuessler
-
Madewell's Insiders Event Is So Good—27 Picks Chic People Will Be Adding to Their Carts
Get 25% off just about everything.
By Jennifer Camp Forbes
-
If You Have Great Taste, You Don't Want to Miss These 30 Chic J.Crew and Madewell Sale Picks
So many gems. So little time.
By Jennifer Camp Forbes
-
I Find Closet Staples at Zara, J.Crew, Banana Republic, Vince, and Madewell—These 30 New Items Are Chic
Sweaters, jackets, suiting, and more!
By Bobby Schuessler
-
I'm Ready to Embrace a Capsule Wardrobe—29 Madewell Items I'm Starting With
It has nonbasic basics on lock.
By Lauren Adhav
-
I'm a Madewell Stan—Here's Every 5-Star Item on My Shopping List
Denim! Classic knits! Cute shoes!
By Kaitlin Clapinski
-
Challenge Accepted: I Created 5 Elegant Winter Outfits From Madewell and J.Crew for Under $452
You're welcome.
By Nikki Chwatt
-
24 Incredibly Chic, On-Sale Sweaters and Jeans to Mix and Match From J.Crew, Madewell, and Abercrombie
Bring on the cool winter outfits.
By Jennifer Camp Forbes
-
6 Chic Winter Outfits From Madewell That'll Have People Believing You Hired a Secret Stylist
I won't tell.
By Eliza Huber