Cheryl Shops

Can you believe that Madewell has been around for almost 20 years now? J.Crew's millennial spinoff debuted in 2006 and pretty quickly eclipsed its older sister just as the Jenna Lyons era was coming to an end—to the point that Madewell was almost spun off into a separate, publicly traded company. I feel like it has had a few ups and downs over the last few years, after its head designer (and secret weapon) Joyce Lee—who has a great Substack, btw—resigned in late 2023; its brand president recently stepped down too, but Madewell has reportedly brought in the jean-ious (bad pun, sorry) Benjamin Talley Smith to revamp its denim line. I've remained a fairly enthusiastic Madewell shopper throughout—they do elevated basics really well, and they've recently been churning out some great dupes of accessories from more high-end designers like Khaite and Toteme. And while Madewell's prices are pretty reasonable to begin with, they have special sales for Insiders several times a year, and to enjoy the discount, all you need to do is sign up for their email list. The current Insiders Event is 30% off sitewide and runs through September 29th. I've already got a shopping bag full of items I can't wait to try, but first, here are the pieces I wear the most and highly recommend.