10 things to buy during the Madewell Insider sale

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.

The Kick-Out Crop is one of my all-time favorite jeans

The Triple Keeper, Skinny Western, and Studded Western belts

I own four Madewell belts, and they're all Khaite dupes. The skinny Western in particular has been a Cheryl Shops bestseller for the last couple of years; I still have all of these on heavy rotation and highly recommend for their power to really elevate whatever you're wearing. I'm in the Triple Keeper below.

Denim, particularly the Kick-Out Crop and the '90s Straight

Madewell has always had great denim; my Kick-Out Crops are one of the most flattering and comfortable pairs of jeans I own, and while they're starting to thin and fade (I've had them for close to 10 years), I still wear them all the time. For both that pair and the '90s Straight, which I'm wearing below, I recommend sizing down!

The Dimes boot

Also a Khaite dupe, I like this one even more than the original and can attest it's comfy AF. This year they're also offering a Chelsea boot but I'm partial to the original back-zip version.

The Whisper tee

Based on the price and low stock, I'm guessing that Madewell is about to phase this one out, which is too bad—I own it in several colors and all have aged beautifully, getting perfectly soft and worn-in without losing their shape or pilling. Hopefully their new Perfect Crewneck tee can live up to its name.

The Harlow Pant

It looks like this one might be on the way out too, which is too bad. This was the first wide-leg pleated pant I was able to tolerate after years of skinnines, and to this day, it's one of my favorites to wear to work.

What's on my shopping list

Lace Pintucked Top

This looks like Isabel Marant and I'm not mad at it. I love tops like this for work—they look feminine under a blazer—and this is such a great price point.

The Essential Bucket Tote

This looks like Toteme, but is a fraction of the price. Suede bags make me nervous, but I'm absolutely in love with the deep maroon color of the leather version.

Longline Cardigan Jacket

I don't really know why they're calling this a jacket when it's clearly just a cardigan, but I love the sleek '90s-inspired shape just the same—it'll be a great layering piece.

Ribbed Polo Sweater

I have a game I like to play, called What Would Kate Moss Wear?, and I think this sweater would definitely qualify. Plus, it's just the right thing to pair with big, baggy pants.

Smocked Waist Miniskirt

I am probably too old to try to pull off a plaid miniskirt, but that's not going to stop me, as this one has strong Isabel-Marant-goes-to-prep-school vibes.

Cheryl Shops