Style Sessions

Welcome to Style Sessions, where our experts share their top fashion tips, trend insights, and outfit inspiration. Elevate your style with guidance from the pros.
18 Pins
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Two ways to style the Rail Straight, our infinitely wearable straight-leg. With Emily, our style director.
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How to Style the Rail Straight Jeans
Two ways to style the Rail Straight, our infinitely wearable straight-leg. With Emily, our style director.
Two ways to style the Low-Slung Baggy. One versatile fit for endless possibilities. With Emily, our style director.
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How to Style the Low-Slung Baggy Jean
Two ways to style the Low-Slung Baggy. One versatile fit for endless possibilities. With Emily, our style director.
How to Style Denim for Spring
Spring style, brought to life by The Wide Sweep, Low-Slung Baggy and our Style Director Emily Newnam.
The art of layering, featuring our Style Director in our updated Superwide-Leg Jean with an even wider leg and elongated inseam.
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How to Master the Art of Layering
The art of layering, featuring our Style Director in our updated Superwide-Leg Jean with an even wider leg and elongated inseam.
Light-as air, luxuriously soft. Words can’t quite describe what wearing new Softdrape Denim can. Our style director Emily shows us two ways to wear it.
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How to Style Softdrape Denim
Light-as air, luxuriously soft. Words can’t quite describe what wearing new Softdrape Denim can. Our style director Emily shows us two ways to wear it.
October’s Style Sessions with Emily, our styling director—featuring two classic looks in the Madewell x Kaihara Superwide-Leg.
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How to Style the Superwide-Leg Jean
October’s Style Sessions with Emily, our styling director—featuring two classic looks in the Madewell x Kaihara Superwide-Leg.
How to Style the Darted Barrel-Leg Jean for Spring
The new Barrel for spring—a lighter wash, a raw hem, and two ways to wear it.
Low-slung, slightly distressed with a relaxed leg—our style director's take on our new forever fit, the Dean Easy Straight.
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How to Style The Dean Easy
Low-slung, slightly distressed with a relaxed leg—our style director's take on our new forever fit, the Dean Easy Straight.
For us, denim is always the starting point, and changing up the denim based on your mood or the occasion makes a big difference. Our style director Emily shows us how to dress up denim.

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How to Dress Up Your Denim
For us, denim is always the starting point, and changing up the denim based on your mood or the occasion makes a big difference. Our style director Emily shows us how to dress up denim.
A ’90s revival. Here are two ways our style director wears our best-selling throwback fit.
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How to Style The 90's Straight Jean
A ’90s revival. Here are two ways our style director wears our best-selling throwback fit.
How to Style the Balloon Jean
The Balloon Jean, a new dark-rinse silhouette—and two ways to wear it.
The '70s fit—cropped, high rise and flared. Our Style Director shows us how to wear it.
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How to Style the Flared Wide-Leg Jean
The '70s fit—cropped, high rise and flared. Our Style Director shows us how to wear it.
How to Style White Denim with Madewell
In this week’s Style Sessions: white denim and two ways to wear it.
Our third and final chat, Jake Woolf covers the bases on styling selvedge denim. The same way antique cars are reveled for their timeless charm, the Japanese fabric behind our 1991 Straight Jean carries the same appeal. Woven using old-school techniques, each pair is unique to the wearer...and ages like a fine wine.



Style Sessions with Jake Woolf. A series focused on denim.
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Style Sessions with Jake Woolf: How to Style Selvedge Denim
Our third and final chat, Jake Woolf covers the bases on styling selvedge denim. The same way antique cars are reveled for their timeless charm, the Japanese fabric behind our 1991 Straight Jean carries the same appeal. Woven using old-school techniques, each pair is unique to the wearer...and ages like a fine wine. Style Sessions with Jake Woolf. A series focused on denim.
In our second convo with Jake Woolf, we get his two-cents on styling wide-leg denim. “Don’t overthink it,” says Jake. A solid mantra to live by, clothes notwithstanding. Beloved pieces can add a bit of comfort when you’re trying something new—so let loose. And don’t overthink it. 

Style Sessions with Jake Woolf. A series focused on denim.
0:49
Style Sessions with Jake Woolf: How to Style Wide-Leg Jeans
In our second convo with Jake Woolf, we get his two-cents on styling wide-leg denim. “Don’t overthink it,” says Jake. A solid mantra to live by, clothes notwithstanding. Beloved pieces can add a bit of comfort when you’re trying something new—so let loose. And don’t overthink it. Style Sessions with Jake Woolf. A series focused on denim.