44 Fall Clothes From Madewell That Will Become Closet Staples
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Here at Swift, we’re Madewell fans. The US brand carries a huge variety of clothing that ranges from girl-next-door to comfy chic to simple minimalist, and with just over 150 stores in the US, you may have a Madewell near you.
Madewell is best described as a place to find “reaaaally perfect” jeans and denim, as well as closet staples like tops, bags, shoes, and accessories. You can curate an entire wardrobe from Madewell, and as someone who has done practically that, you can trust that there are all kinds of closet staples that will help you look chic, comfortable, and well-dressed all season long.
Prepare First: Gather What You Already Have
Capsule wardrobes are a hit, but they don’t work unless you have clothing pieces that you like to wear often and can mix with other items in your closet. There are, of course, classic closet staples: a white button down, gold hoop earrings, a blazer, and loafers that can add a timeless and sophisticated touch to any outfit pairing. Most closets also contain the seasonal fall favorites: a flannel shirt or shacket, tall socks, a turtleneck, mom jeans, combat boots, and outerwear.
And we all have our go-to items, as well; for some it may be a leather skirt or favorite designer purse. Though for me, it’s a pair of black leggings and an oversized sweater that feels like a hug. Regardless of what’s already in your closet, get a feel for what your wardrobe staples are and aren’t; this will show you what items to style around and what items it would be wise to shop for.
Then Make A Shopping List
I don’t know about you, but if I don’t start a shopping spree with some kind of idea—even if it’s just a folder of Pinterest screenshots featuring trendy fall clothes—I end up buying more than I want and making impulsive purchases that I later regret and return. So, being prepared is an all-around feel-good practice that I can wholeheartedly recommend.
You can keep this step low-key by making a mental note or a note in your phone about what you’re looking for. Maybe it’s a new pair of denim skinny jeans or a sweater vest (Madewell has options for both!). You can also get more granular and online shop Madewell’s site before you shop in-store to see what styles are available and create an accurate mental image of what your closet could look like.
Start Shopping Madewell’s Deals This Fall
Shopping is the fun part, right? Madewell has great clothes year round, including denim and everyday essentials, but the brand’s clothing really shines in the fall when you can wear multiple layers. Here are seven Madewell styles that are perfect for fall and will pair well with the items you already own.
Tall Leather Boots
There’s something about a tall boot that practically screams fall. Calf or knee-high leather boots are one of the most popular footwear choices for fall, both because they’re practical for the cooler weather and because they give off an effortless vibe. When paired with a short skirt or dress, boots make your body look taller as well as catering to cool mornings and warm afternoons. You can also wear this style with fancier clothes for an event or layer with more casual clothing like flannels, sweaters, and jeans.
Our Inspiration:
Shop: The Antoine Tall Boot
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The Monterey Tall Boot
This classic boot features leather that comes from a Gold-rated tannery, as well as a two-inch heel and zipper that makes putting them on a breeze. They also come in half sizes, which is a huge plus for those with half-sized feet or for keeping the boots comfy when wearing thicker socks.
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Leather CouCou Tall Boots
Intentionally Blank
These boots are a dual threat: they can be worn tall and straight or scrunched down to create two different styles. Made of leather both inside and out, the boot has a classic silhouette that pairs with just about everything.
Image: Madewell
The Drumgold Boot
If you like a bit of shine, you’ll want to try this flat black boot. The 15” height will land just below your knee, making these great for layered looks or staying warm and dry on blustery days.
Chunky Sweaters
When autumn arrives, a chunky sweater becomes a cherished wardrobe item; its warmth is a cozy hug against the crisp air. When paired with jeans the casual style epitomizes fall, or when worn atop a dress or layered with outerwear when the sun goes down. While sweaters go with everything, don’t be afraid to make them the focal point of your outfit. Bonus points if it’s vintage or homemade!
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Tipped V-Neck Oversized Sweater
Dress in comfort and style with this oversized v-neck sweater. With its tipped detailing, it's easy to match with similar colors for a preppy or laid-back OOTD. Versatile for layering or as a standalone piece, it's a fall essential.
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Rugby Stripe Polo Sweater
This striped polo sweater combines a sporty and sophisticated rugby vibe. Its cozy knit design makes it a standout choice for both casual outings and polished occasions. It’s also a perfect layer to keep with you for changing weather or beach days.
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Crochet Knit Crop Sweater
Crochet styles are popular and perfect for the autumn season. The loose weaving helps you stay cool, while the varying patterns keep your outfit interesting. And who doesn’t love a cropped sweater?
Cozy Pants
Cozy pants are basically my character outfit—you know, what you’d wear if you were in a cartoon. Elastic waist pants, especially options with drawstrings, redefine relaxation on lounge days, adapting effortlessly to your daily routine. You’ll want more than one pair of comfy sweats to mix and match with button-downs, sweaters, and your favorite pair of moccasins.
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(Re)Sourced Fleece Roll Sweatpants
Madewell x Donni Pearl
Dive into cozy chic with these (re)sourced, roll-top sweatpants from the Donni Pearl collaboration. Crafted for comfort and sustainability, they're ideal for relaxed days or pairing with a casual-chic ensemble.
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Ribbed Pull-On Flare Pants
Mix texture into your casual collection with these ribbed pull-on flare pants. The soft material adds dimension to an outfit, while the flare silhouette brings a hint of flair. These are versatile and comfortable for both lounging and going out.
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Donni Waffle Roll Pants
This pant’s waffle texture adds depth, and the relaxed fit guarantees day-long comfort. Dress them up or down for a versatile fall addition, made easy thanks to the neutral color.
Denim Overalls
Overalls add charm to fall wardrobes. Beyond their nostalgic flair, they inspire creative, curated looks ranging from whimsical to rugged. Their genius lies in their adaptability—perfect for navigating the unpredictable shifts of seasonal weather, whether paired with a lightweight tee and sandals for warm afternoons, or layered with chunky sweaters and ankle boots for cool nights.
Our Inspiration:
Shop: Denim Seamed Zip-Up Jumpsuit in Laurelhurst Wash
Our Favorites:
Image: Madewell
Denim Carpenter Overalls (Copley Wash)
You can never go wrong with a traditional pair of denim overalls. This versatile piece offers a playful style, ideal for creating many trendy looks for fall.
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High-Rise Loose Flare Overalls (Ashlane Wash)
Channel retro vibes with the perfect vintage flare overall. Its classic design is complemented by low-stretch Cone® denim, a high-rise fit, and zippered hardware.
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Oversized Denim Overalls (Tile White)
These oversized carpenter overalls update your denim game with a relaxed silhouette and detailed stitching that blends comfort and style perfectly for fall.
Midi Skirts
Midi skirts bring an air of sophistication to your seasonal wardrobe. Whether it’s with simple, solid colors or intricate patterns, midi skirts effortlessly elevate any ensemble and keep you from feeling too overdressed—both for the occasion and the weather. From cozy sweaters to tailored blouses, a midi styles well with various tops, allowing you to curate looks with items you already have.
Our Inspiration:
Shop: Layton Midi Slip Skirt
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Denim Mid-Rise Maxi Skirt (Pineland Wash)
This mid-rise denim skirt has a medium wash with an eye-catching front slit. The Pineland-inspired wash makes it easy to dress up with a purse or jewelry.
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Overlap Midi Skirt
Reistor
Hang on to the dwindling days of summer with this blue and white striped midi-skirt. This nature-inspired skirt is perfectly suited for everything from the classroom to a wedding.
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Antique Pull-On Skirt
World of Crow
This cottage-core dress will make you want to tend to the garden. The rich, rustic brown is the perfect neutral to easily match with sweaters and footwear, while the pull-on waist ensures a relaxed fit.
Quilted Outerwear
Quilted outerwear is a fall favorite that fuses form with function. Beyond its aesthetic allure, this outerwear style is also practical with water-resistant fabric and a lightweight feel. The detailed stitching patterns are not only visually appealing, but keep you from looking like a singular puff ball. Wear these with everything from tailored trousers to well-worn jeans, or even atop an evening dress or flowy skirt.
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Quilted Bomber Jacket
The cozy-chic oversized bomber jacket comes in both standard and plus sizes, so everyone can add it to their cart. Its generously-sized shape fits over thick layers, while the rich fall colors effortlessly complement other wardrobe pieces. The lightweight design is everything you need to transition into the cooler season.
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Quilted Oversized Puffer Vest
If you aren’t ready to commit to a jacket, try this quilted vest instead. With its lightweight construction, this vest adds warmth without bulk, perfect for layering or wearing as a statement piece, with the waist tied in a cute bow or hanging loose.
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Alba Overshirt
Woolrich
For a top-tier laid-back fall aesthetic, try this soft plaid overshirt. The rustic look makes it feel more like a favorite flannel or shacket than a puffer jacket, so it’s the best of both worlds.
Light-Wash Jeans
Light-wash jeans are the style equivalent of a breath of fresh air. Their light shade keeps outfits bright without venturing into summery territory. Ideal for both back-to-school outfits and laid-back weekends, these jeans complement a range of looks. Pair them with a crisp button-down and a blazer for a polished yet approachable ensemble, or dressed down with a simple tee for a casual, confident statement.
Our Inspiration:
Shop: The Curvy '90s Straight Jean in Mercer Wash
Our Favorites:
Image: Madewell
Crossover Baggy Straight Jean
Madewell x Molly Dickson
The crossover button closure is popular, and we know why: it helps to accentuate your curves and gives you an hourglass figure without doing anything but buttoning up. These baggy-straight jeans are comfortable all day long whether you’re walking to class or working from home.
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Kick Out Crop Jeans (Mather Wash)
Are slim jeans still a thing? We think so! These cropped “kick out” flare jeans are just right for fall, complete with a mid-rise waist, authentic fading, and denim that stretches with you instead of constricting your skin. (Plus, they come in a huge variety of washes!)
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The Maternity Side-Panel Slouchy Boyjean (Wrightlane Wash)
Moms can wear jeans, too, even when pregnant. This pair of maternity jeans has ripped knees and an ultra-icy wash that makes you the coolest mom-to-be on the block.
Blazers
With their sleek lines and laid-back charm, blazers effortlessly dial up any look. Wear them over a crisp button-down and your favorite jeans for a low-key, put-together vibe. Or throw one on with a graphic tee for that 'just grabbed it off the chair' cool. Blazers are the secret sauce – they blend tailored elegance with an "I woke up like this" ease, making your autumn-style game strong without breaking a sweat.
Our Inspiration:
Shop: Dorset Crop Blazer
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Image: Madewell
Oversized Knit Houndstooth Blazer
Blazers with a structured shape are great, and they’re even more fun to style when they have a pattern. This Houndstooth style elevates your outfit even if it’s just a white tee.
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Rumpled Terry Blazer
For those who live in hot climates or aren’t ready to say goodbye to summer, opt for this lightweight cotton blazer. It’s rumpled intentionally, so you can dress it up or down with accessories.
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Dorset Blazer
Another patterned option is this plaid number. It has a slouchy yet snug fit for a tailored-like look that will leave you feeling comfortable and confident even if you’ve got a big day ahead.
More Essentials to Keep in Your Closet For Fall
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Amalia Boot
Nisolo
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