Madewell has always been one of my favorite places to shop for pieces that feel both timeless yet trend-forward. So, when I spotted the brand’s massive fall sale, with an extra 50 percent off sale styles using code “LONGWEEKEND,” I knew my wallet was in trouble (in the best way). The discounts are too good to scroll past—think wide-leg jeans for just $30, tailored trousers marked down a whopping 83 percent, and more travel clothes that make packing for any fall trip a breeze.
From midi dresses to comfy mules and lightweight cardigans, the sale section is filled with elevated staples you’ll want to live in all season long. Prices start at just $20, but with deals this good, sizes are going fast. Trust me, you’ll want to shop before the long weekend (and these markdowns) come to an end.
Best Overall Madewell Fall Sale Finds
Denim Scoopneck Midi Dress
Madewell
This 100 percent cotton denim midi dress is fall’s answer to effortless dressing. It’s light enough to wear solo while temps are still in the 60s and 70s, but layers beautifully under a trench or blazer once it cools down. With pockets (always a win) and a versatile silhouette, it’s an easy pick for travel—just swap sneakers for boots or loafers to instantly change the vibe.
The Slouchy Straight Pants
Madewell
Now a shocking 83 percent off, these straight-leg pants are the pair I practically live in. They strike that perfect balance of relaxed and refined—soft and comfy enough for a long flight, yet structured enough to wear straight to dinner. At just $20, they’re a total steal and endlessly versatile: pair them with a tee and sneakers for travel days or a sweater and ballet flats for a sophisticated fall outfit.
The Greta Ballet Flat Mule
Madewell
I love a good mule because you get the elegance of a ballet flat without that dreaded heel rubbing (truly a game changer). This studded leather pair adds a subtle pop to any outfit—whether you’re in jeans, trousers, or something dressier. Plus, the brand’s Cloudlift Lite padding makes every step feel cushy and supported. At 61 percent off, these are the kind of shoes you’ll find yourself slipping on every single day.
Ribbed Polo Sweater
Madewell
The polo sweater trend isn’t going anywhere, and this one nails that preppy-yet-polished vibe. The oversized buttons give it a little something extra, and the ribbed knit feels soft but lightweight—perfect for layering under a coat or over a tee. Wear it to the office, on a date night, or for a travel day when you want to look pulled together without trying too hard. Even better? It’s only $40 right now.
Superwide-leg Jeans
Madewell
These jeans are the fall denim steal—just $30 for a pair that feels designer-level. The dark blue wash complements every autumn shade, from chocolate brown to camel, and the wide-leg cut is both flattering and on-trend. Inspired by ’90s silhouettes, they’re easy to dress up or down, and they’re an absolute must if you love that effortless, cool-girl travel uniform.
Smocked Long-sleeve Top
Madewell
This top turns a basic long sleeve into something special with its voluminous puff sleeves and smocked cuffs. The lightweight cotton jersey keeps it breezy and comfortable, so it’s ideal for travel or everyday wear. Style this blouse with trousers and a suede belt like the model—or dark denim and boots for a chic fall look. And at just $25 right now, it’s a no-brainer addition to your cart.
Utility Wide-leg Trousers
Madewell
These wide-leg pants are where comfort meets cool. They mix the practicality of a utility pant with the sophistication of a trouser, featuring cargo-style pockets and a casual, lived-in feel. They’re dressy enough for brunch or the office but comfy enough for a long-haul flight. I’d wear them exploring a new city like London or Copenhagen with sneakers and a tucked-in tee.
Pointelle-knit Cardigan Top
Madewell
A lightweight cardigan is a fall essential, and this one is too good to pass up at just $23. The charcoal grey hue and textured ribbing give it that cozy-meets-chic appeal. You can wear it buttoned up as a sweater or open over a tank with a belt and Mary Janes for a complete look. It’s the perfect transitional piece for layering through the season.
Asymmetrical Ruched Midi Dress
Madewell
Polka dots are back in a big way, and this romantic midi dress proves why. The asymmetrical ruching at the waist creates such a flattering shape, and it transitions effortlessly between seasons—pair it with kitten heels and a blazer for fall, boots and a faux fur coat for winter, or strappy sandals come spring. It’s one of those wear-anywhere pieces you’ll reach for all year.
The Darted Barrel-leg Jeans
Madewell
Lucky you— we just found the perfect pair of barrel jeans for just $60. The light wash makes them easy to style a million ways: go casual with a striped tee and retro sneakers, wear a button-down and loafers for the office, or pair with a sweater and trench for fall travel. The praising reviews say it all: “I needed a good [pair of] jean[s] for traveling that [were] comfortable enough to sit on the plane in, and this really did the trick while looking incredibly chic.”
Bubble Tee
Madewell
The Bubble Tee has earned a top spot in my closet, because I reach for it constantly. The subtle stripes add just the right amount of pizzazz, and the bubble hem plus boat neckline give it a stylish touch. It’s super versatile—I’ll wear it with blue jeans and a brown jacket one day, then switch it up with white pants for a crisp fall whites look. It’s just $20 right now, which feels like highway robbery for how often you’ll wear it.
The Cleo Straight Jeans
Madewell
The Cleo Straight Jeans are sitting high on my wish list. The denim wash is chef’s kiss, and the front pockets add a unique, elevated twist. With a high rise and straight-leg silhouette, they’re the kind of everyday jeans that work for errands, travel days, and everything in between. They’re timeless, flattering, and easy to dress up or down, no matter where you’re headed.
V-neck Cutaway Vest in Corduroy
Madewell
Corduroy is having a major moment, and this vest is right on trend. The green hue is peak fall, and it looks especially good styled with the matching corduroy pants for a monochrome moment. It’s also easy to layer—throw under a blazer or trench when the temperatures drop.
The Essential Curve Crossbody Bag
Madewell
I’m a fan of Madewell’s bag collection, and the Essential Curve Crossbody Bag is the standout—especially at 64 percent off. The suede finish and subtle stud detailing instantly elevate any outfit, while the warm brown tone adds a fall-ready touch. It’s roomy enough for travel essentials (it will fit an iPad, water bottle, wallet, keys, etc.) and features a secure top zipper and interior pocket for peace of mind. Plus, the adjustable strap lets you wear it crossbody or over the shoulder, depending on your day.
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