The 10 fall staples a fashion editor and former Madewell employee is grabbing during Madewell’s Insiders Event. The sitewide sale includes 25 percent off cashmere sweaters, leather handbags, wide-leg jeans, and more.

Cashmere, leather bags, and more are on rare discount.

Madewell’s Insiders Event—which is going on right now—is kind of like an unofficial holiday for its loyal shoppers (me). Given that it only happens twice a year, the sale is a rare opportunity to save on nearly everything, including often-excluded new arrivals, cashmere, and leather. So, of course, I never miss it. 

With almost all of the brand’s new arrivals now 25 percent off for Insiders, I went on a bit of a shopping spree. (Not an Insider yet? You just need an email address to create an account.) Below, find everything I—a former Madewell employee—am eyeing during the sitewide sale, including cashmere sweaters, classic jeans, trending bags, and more. 

Best of Madewell’s Insider Sale

• Bouclé-Knit Crewneck Sweater Tee, $51 (Originally $68)
• Slouchy Straight Pants, $89 (Originally $118)
• Poplin Smocked Bubble Midi Skirt, $89 (Originally $118)
• The Perfect Vintage Wide-Leg Jean, $104 (Originally $138)
• Puff-Sleeve Midi Dress, $104 (Originally $138)
• Belted Oversized Trucker Jean Jacket, $111 (Originally $148)
• Cashmere-Wool Blend Polo Sweater, $126 (Originally $168)
• The Grayson Penny Loafer, $134 (Originally $178)
• Cashmere Button-Front Cardigan Sweater, $134 (Originally $178)
• The Essential Medium Bucket Tote Bag, $141 (Originally $188)

Cashmere Button-Front Cardigan Sweater

Orig. $178 $134 at Madewell.com

Madewell’s cashmere is almost never included in sitewide sales, so I always snag a sweater or two when it is marked down. With cashmere, I always gravitate toward classic styles I can wear for years (I consider it an investment), which is why I’m picking up this simple cardigan. The fitted sweater is timeless and incredibly versatile—I plan to recreate this effortlessly cool Dakota Johnson look—while the color options, including a rich chocolate brown, are on-trend this fall.

The Perfect Vintage Wide-Leg Jean

Orig. $138 $104 at Madewell.com

I’m loyal to wide-leg jeans (trends be damned!) so I’m of course grabbing the Perfect Vintage style while it’s on sale for $104. The jeans feature a wide-but-not-overwhelmingly large leg and are available in a faded dark wash that’s perfect for fall. And while most vintage-inspired styles are made entirely from cotton (a.k.a they’re super stiff), this one has a tiny bit of spandex, which gives the style some stretch.

Bouclé-Knit Crewneck Sweater Tee

Orig. $68 $51 at Madewell.com

This sweater tee is my must-have transitional piece. I’m obsessed with everything about it, from the bouclé knit—which adds much-need texture to a pair of sleek trousers or classic jeans—to the slim fit. And while it’s available in both a solid white and blue, I’m leaning toward one of the stripe options; between that bold pattern and cozy texture, you don’t have to add much else to make this outfit feel complete.

Poplin Smocked Bubble Midi Skirt

Orig. $118 $89 at Madewell.com

Bubble skirts were one of summer’s biggest trends, and this full-length style brings it into fall. Candidly, the super tiny ones that dominated the past few months were a little too youthful for me, but I find this ankle-grazing style to be quite elegant. While the style dresses up with ease (a fitted black bodysuit and pumps would look beyond chic), shoppers say it works just as well when worn more casually.

Madewell’s Insider Sale is one of the rare times you can save on almost everything. Take advantage of the 25-percent-off sitewide sale and shop more of my top picks, below.

Puff-Sleeve Midi Dress

Orig. $138 $104 at Madewell.com

Cashmere-Wool Blend Polo Sweater

Orig. $168 $126 at Madewell.com

Belted Oversized Trucker Jean Jacket

Orig. $148 $111 at Madewell.com

Slouchy Straight Pants

Orig. $118 $89 at Madewell.com

The Essential Medium Bucket Tote Bag

Orig. $188 $141 at Madewell.com

The Grayson Penny Loafer

Orig. $178 $134 at Madewell.com