Top 10 Madewell September Favorites

The 10 Best Things To Buy On Madewell This Fall

The 10 Best Things To Buy On Madewell This Fall

Crisp air and hot coffee orders may still be a distant reality for the Rank & Style staff (we do live in Texas, after all), but you can best believe we're still stocking our carts and closets with all kinds of dreamy new-season essentials. While we've been doing some digging at a number of retailers, we're seriously impressed with the selection of fall finds at Madewell right now. The site is currently chock-full of chic but practical styles perfect for wearing all season long, and best of all, many of them rank high in the comfort department—think cushy but cool sneakers, paper bag pants that are just as polished as they are lounge-worthy, and the coziest high-rise jeans you'll ever slip into. Ahead, we're giving you a peek at all of those styles and more so you can snag them for yourself. From fall-ready florals to the new way to wear tie-dye, keep scrolling for the lowdown on the Madewell finds we'll be buying for the season ahead. Opening image: madewell.com

Love our 10 Best Madewell September Favorites? Check out our 10 Best Denim And Chambray Shirts next!

Jump To Products

September 15, 2020

FacebookPinterest logoTwitter logoEmail icon

Top 10 Lists serve as unbiased shopping guides to the most trusted product recommendations on the internet. Products are scored and ranked using an algorithm backed by data consumers find most valuable when making a purchase. We are reader-supported and may earn a commission when you shop through our links.

The Rankings

Madewell Dolman-Sleeve Ruffle-Hem Midi Dress
Rank & Style Approved


Madewell Dolman-Sleeve Ruffle-Hem Midi Dress

LOVED FOR: No need to say goodbye to floral dresses just because it's fall. With its midi length, moody print, and dolman sleeves, this little number is the perfect new-season update.

STYLE WITH: Pair this pretty dress with black high tops and a denim jacket for a fall-ready look.

Madewell Daily Shirt

BEST FOR: Button-down shirts just keep getting better, don't they? This one has cuffed short sleeves and a touch of linen for a breezier feel, so it's perfect for those warmer pre-fall days.

HELPFUL TIP: Stick with your regular size for a slouchy, borrowed-from-the-boys look, or size down for a closer fit.

Madewell Colburne Cardigan Sweater

WHY YOU NEED IT: Crafted with Madewell's signature Coziest Yarn, this sweater is soft enough to wear buttoned up as a top. Lucky for you, the grandma trend just so happens to be super in right now.

USERS SAID: "I love love love this cardigan! It’s very soft and plush, and overall it looks and feels high end. The color (forest green) is true to the picture and fits true to size as well. I threw it on over a pair of overalls and felt like I belonged in the corner of a cozy library."

Madewell The Perfect Vintage Jean In Enmore Wash

LOVED FOR: Unlike your standard pair of vintage high-rise jeans, these beauties have some seriously comfortable stretch to them—no need to worry about them digging into your midsection when you sit.

USERS SAID: "These jeans are perfection—my favorite from Madewell, and that’s saying something. They have the perfect super high, vintage look with juuuust enough stretch to make them incredibly comfortable. I wear a 28 in skinny/super stretch denim and sized down to a 27 in these."

Madewell Tie-Dye Swing Sweatshirt

WHY YOU NEED IT: New season or not, tie-dye definitely isn't going anywhere. With its sandy shade and cozy fit, this sweatshirt is the perfect way to carry the trend into fall.

FUN FACT: Just in case you need another reason to love it, this sweatshirt is earth-friendly thanks to recycled cotton.

Madewell Kickoff Trainer Sneakers In Leather And Spot Mix Calf Hair

LOVED FOR: A retro silhouette and on-trend prints make these sneaks the perfect blend of old school and modern. Even better? They're made with MWL Cloudlift insoles for a super cushy fit that feels like walking on a cloud.

FUN FACT: These chic sneakers are made with recycled cotton and sustainable leather. Way to go, Madewell.

Madewell Knit Cami Midi Dress

WHERE TO WEAR: Meet your new do-it-all dress. With the switch of a shoe, you can easily take it from daytime errands to drinks on a patio.

USERS SAID: "This dress is the best purchase I've made this year. It is stylish and super comfortable, and the olive green is so sophisticated and flattering for all skin tones—transitions wonderfully to fall. A racerback bra is perfect for a nearly no-show look. Looks like a very high-end dress that would be worth it at full price, though on sale, it's an incredible buy."

Madewell The Carina Boot

WHY YOU NEED IT: Fall boots are rarely this good looking and this comfortable. With gorgeous leather and cushy, padded insoles, they're the perfect blend of fashionable and functional.

STYLE WITH: Pair them with your favorite ankle-length jeans to show them off.

Madewell Drapey Paperbag Pants

LOVED FOR: Not only are these insanely flattering thanks to the paper bag waist, but the satin-backed crepe makes them incredibly comfortable, too. These beauties may just give your favorite jeans a run for their money this season.

WHERE TO WEAR: We know what we'll be wearing when we head back to the office.

Madewell 10" High-Rise Skinny Jeans In Hayes Wash

BEST FOR: If you prefer your jeans with a sky-high rise, look no further than these. The waist comes up 10 inches for an ultra-flattering look.

FUN FACT: They also come with Madewell's Magic Pockets, so they'll make your tummy look extra slim and smooth. We'll take one in every wash.

View All Top 10 Lists
Arrow white

The Latest

Image credits: anthropologie

Blouses & Shirts

Affordable Trending Blouses

We Found 20 Pretty Summer Tops—And They All Ring Up Under $100

View All Womens

From Our Partners

Image credits: jane iredale

Jane Iredale

Meet TikTok's NEW favorite eye shadow stick, ColorLuxe by Jane Iredale.

Shop Now

Arrow white

Straight-to-the-point emails to make finding what you love even easier.