10 Fall Staples a Former Madewell Employee Is Buying From Its Biannual Sale

Madewell has semi-frequent sales — an extra discount on already marked-down items here and a small percent off select styles there — but there’s one in particular that I patiently wait for to do my restock. And no, it’s not Black Friday: Madewell’s Insider Event is the sale I plan my wardrobe overhaul around every fall, and all you need to access it is an email address.

Even as a former employee who got pretty accustomed to the steep employee discount, I religiously shop this sale because nearly the entire brand is 25 percent off, including the rarely-discounted leather goods and cashmere. It also usually happens in tandem with the release of the brand’s fall collection, giving you immediate discounted (!) access to the season’s must-have pieces. So as someone who has been on both sides of the sale, I sorted through the expansive lineup to find the must-grab items — sure-to-sell outs, wardrobe staples, and those never-discounted pieces — and narrowed it down to these 10.

• Signature Poplin Oversized Shirt, $64 (Originally $85)
• The Greta Ballet Flat, $74 (Originally $98)
• The Rosedale High-Rise Straight Pant in Crepe, $89 (Originally $118)
• The Basketweave Mini Crossbody Tote in Leather and Suede, $96 (Originally $128)
• Brushed Argyle Crewneck Sweater, $96 (Originally $128)
• Lightspun V-Neck Midi Dress, $96 (Originally $128)
• Superwide-Leg Jeans, $104 (Originally $138)
• Cashmere Oversized Crewneck Sweater, $111 (Originally $148)
• The Larsen Blazer in Mixed Plaid, $149 (Originally $198)
• The Monterey Tall Boot, $224 (Originally $298)

The first thing I did when I learned that the Insider Event was happening was search for cashmere, finally ready to grab an often-excluded-from-promos sweater. Madewell’s cashmere is, in my experience, uber-buttery, itch-free, and long-lasting, which is why I’m eyeing the 100-percent cashmere Oversized Crewneck Sweater. Because it holds up so well (and is a bit of an investment), I want something timeless rather than trendy, and this classic crewneck is just that. According to shoppers, it is a “beautiful sweater” that can be “dressed up or down” and is “soft to the touch.” A number of people raved about the recently-added Roasted Squash shade, too. “The color is something you would expect from luxury brands,” wrote one person, adding that the burnt red shade “can go with anything.” 

Cashmere Oversized Crewneck Sweater

Of course, after reading what InStyle writer Jailynn Taylor had to say about the brand’s recently-added Rosedale High-Rise Straight Pants in wrinkle-resistant crepe, I had to add them to my cart. Per her review, this pleated trouser is shockingly comfortable, and she went so far as to deem them her “professional sweatpants.” “They are more polished than jeans and sweatpants but just as comfy as the latter,” she wrote. And personally, I love how a loose-leg trouser can instantly elevate a wardrobe basic without feeling stuffy — it’s the cool-girl look Jennifer Lawrence has mastered. For fall, I’m eyeing the chocolatey brown shade, but this is also available in five other colors, including a classic black, acorn brown, and a deep ocean blue.

The Rosedale High-Rise Straight Pant in Crepe

Mary Janes have been 2023’s ‘It’ shoe — the cutesy but practical style is a staple across every generation — so I will absolutely be grabbing the brand’s leather Greta flats while they’re 25 percent off. I adore Madewell’s leather shoes. If you need an idea of how well they hold up, know that I bought a pair five years ago, wore them what I figured would be into the ground, and somehow still find myself pulling them out (and getting complimented on them!) to this day. And according to an InStyle writer that already owns this exact pair in silver, this style is “just the right mix of feminine and modern” and “super comfortable…thanks to Madewell’s Cloudlift Lite padding in the insole.” And shoppers agree, calling them “versatile and functional.” “I walked for miles the first day I wore them,” wrote one customer. And another person said that they were comfortable right out of the box “with no break-in time needed.”

The Greta Ballet Flat

From the sale, I’m also eyeing a pair of trending wide-leg jeans, a new, more-autumnal iteration of the brand’s timeless leather bag, and a blazer that I am counting down the minutes until it sells out. Shop more fall-ready, discounted pieces below.

Brushed Argyle Crewneck Sweater

Lightspun V-Neck Midi Dress

Superwide-Leg Jeans

The Basketweave Mini Crossbody Tote in Leather and Suede

The Larsen Blazer in Mixed Plaid

Signature Poplin Oversized Shirt

The Monterey Tall Boot