PSA: Madewell Is Having Its Insider Sale—Shop These 8 Editor-Owned and Loved Pieces

Curating the perfect fall wardrobe comes down to a science. The formula requires the right balance of classic seasonal staples and new trends, which is essentially Madewell’s bread and butter as a retailer. It’s also ours, as writers and editors that shop for a living. 

With Madewell’s Insider Sale officially in full swing, it felt like the right opportunity to let you in on the denim styles, transitional blazers, and leather accessories we own and can’t live without. The promotion includes 25 percent off the entire site for any and all customers part of the free rewards program. However, if you aren’t already a member, you can sign up here by simply inserting your phone number and email. Once you’re logged into your account, you’ll immediately get access to the exclusive discounts. 

A few must-have items to grab during the sale include these Satin Bow Statement Earrings that have become my most-complimented accessory to date and the easiest way to upgrade an otherwise simple outfit, and this Oversized Knit Blazer in Houndstooth Partnerships Editorial Director Ariel Scotti always reaches for in the fall. Keep scrolling to find out what else the shopping team recommends and is obsessing over this season. 

Editor-Loved Picks to Buy During Madewell’s Insider Sale

• The Sydney Crossbody Bag, $126 (was $168)
• The ‘90s Straight Jean, $104 (was $138) 
• Stovepipe Jeans, $104 (was $138) 
• Oversized Knit Blazer in Houndstooth, $96 (was $128) 
• Whisper Cotton V-Neck Tee, $15 (was $20)
• The Perfect Vintage Wide-Leg Jean, $104 (was $138) 
• Satin Bow Statement Earrings, $21 (was $28) 
• The Sydney Hobo Bag, $89 (was $118) 

The Sydney Crossbody Bag

Ali Faccenda, Partnerships Writer: “These last few months, I’ve been super into handbags that can be worn in various ways. I’m a bit tired of crossbody bags, although I always enjoy having the option to wear it that way if my hands are full. This bag can be worn both as a crossbody and carried as a handbag and is incredibly roomy. I can fit all of my essentials with room to spare for my camera (and even after that, there’s still room left). I have the vapor color, which is a beautiful white that goes with everything in my closet, and I love the smooth leather finish. The bag feels sturdy, looks sleek, and has gotten me loads of compliments.” 

The ‘90s Straight Jean

Lauren Fischer, Partnerships Editor: “I love a good throwback style, so I was excited to test these loose-fitting jeans that made me nostalgic for my youth. I sometimes struggle with pants fitting properly around both my waist and my hips/thighs, but from the first time I slid these on, they hugged both areas perfectly. I appreciate that they have a higher rise in the back (no tugging necessary), which gives my behind a lifted appearance. As I wear them throughout the day, instead of stretching out so much that they appear baggy, these have just enough give to flatter my shape. They stay comfortable all day—even when I work from home—and feel slightly thicker than other denim I own, making them an ideal choice for cooler fall days and chilly winter weather. Plus, at just 5 feet tall, I love that they come in petite sizes, which fall perfectly at my ankle.”

Stovepipe Jeans

Ariel Scotti, Partnerships Editorial Director: “Call me a millennial, but I’ll die before I give up skinny jeans. These are technically straight-leg, but they sit super close to the body, giving me the comfort of the skinnies I love while also feeling a bit more fresh. The black is the truest, most saturated color I’ve found and even after washing, they look just as rich. On top of being comfortable with just the right amount of stretch, these jeans don’t lose their shape throughout the day, and, bonus points, they don’t hold onto lint easily—which can be a pain with black. I see myself wearing these weekly over the next six months.” 

Oversized Knit Blazer in Houndstooth

Ariel Scotti, Partnerships Editorial Director: “Early fall is my favorite time of year to wear blazers. They’re a warm layer that doesn’t get too toasty and have that key ability to instantly elevate any outfit. This houndstooth option ticks all of those boxes and more. The pattern here looks black and cream at first glance, but those threads are woven with light brown, olive green, and sky blue, for even more dimension and interest. The oversized fit looks contemporary without making me feel like I'm drowning in it, and the drop shoulder is slight, which prevents the look from teetering into sloppy. Plus, it’s incredibly soft, so I never want to take it off.” 

Whisper Cotton V-Neck Tee

Ariel Scotti, Partnerships Editorial Director: “These t-shirts are my holy grail; so much so that I own eight of them and am going back for more. The Whisper Cotton v-neck is the softest, most comfortable basic layer that I own and the fit is everything I want in a tee: loose with a hint of shape. The neckline hits at a sophisticated yet sexy place in the upper center of my chest, and although the shirt has some stretch to it, it never becomes boxy. These shirts don’t shrink in the wash and only get softer the longer you own them and, as someone who has them in several colors, I can say for sure that they don’t fade over time either.” 

The Perfect Vintage Wide-Leg Jean

Bridget Degnan, Partnerships Editor: “The name of these jeans couldn’t be more fitting because they are truly the most perfect pair of wide-leg denim I own. To give you some insight, I’m 5 feet tall on a good day, so shopping for pants to fit my petite frame is a struggle—especially baggy styles. But as you’ve probably heard, loose jeans are trending, so despite my concerns, I requested a pair of Madewell’s wide-leg jeans as a sample. The petite sizing pretty much guaranteed that they’d be the right length, but I didn’t know until I tried them on that they would be so flattering from my waist down to my ankles. They hug my hips and thighs in all the right places and then a tasteful amount of bagginess in the bottom half. Petite or not, you need these jeans.” 

Satin Bow Statement Earrings 

Megan Schaltegger, Partnerships Writer: “I’ve never received so many compliments on a pair of earrings than with this Satin Bow style. They feel like the definition of a statement jewelry piece thanks to the combination of eye-catching gold-plated brass and exaggerated black bows. I love pairing the earrings with an otherwise simple outfit or sleek pinned-back hairstyle to let them do all the talking. The lightweight design makes them comfortable for long wear, while the bold style adds an element of interest to any look.”

The Sydney Hobo Bag

Megan Schaltegger, Partnerships Writer: “I have been all-aboard the mini bag train for quite some time, but despite my dedication to the trend, I’ve struggled to find a style that comfortably fits my shoulder and is roomy enough to store my day-to-night essentials. Madewell’s Sydney Hobo Bag manages to do both. The buttery soft leather, which comes in classic black, brown, and white, looks and feels luxurious, while the knotted straps give this everyday bag an added flair. The magnetic closure is also strong enough to protect my precious contents from accidentally spilling out but offers easy access nonetheless when I need to whip out lip gloss or my beloved mini brush for mid-night touch-ups.” 

Head over to Madewell to shop our favorites for fall, and remember to sign up for the Insider program while you’re at it so you can get 25 percent off everything on the site.