Madewell says it was introduced in 2006 as a premium denim brand, and its own story is unusually plain about what it believes: great denim is forever. I like that as an answer to the fashion cycle. A pair of jeans can feel current without looking like it came from one particular year.

 

Madewell jeans read like a small argument with the skinny era: there is room for a wide leg, a straight leg, a barrel, a crop and a flare, without pretending one is the only right answer. I would start with the cut before the wash, since the cut decides whether the pair feels relaxed, neat or a little theatrical.

 

The Super Stretch Denim Wide Leg has a clean fall; the Emmy Patch Pocket pair brings a high rise and squared pockets; The Ultimate Wide-Leg Jean in Airy Denim has a softer finish and a drawstring; Low Slung Baggy Jeans relax the rise and add knee patches. They are not four versions of one idea. Pocket shape and rise change the proportion more than a new wash ever could.

 

Four newer pairs widen the choice: The Perfect Vintage Wide-Leg Jeans In Airy Denim in a mid blue Bedford wash, The Perfect Vintage Crop Jeans in canvas, the Madewell x Shopbop Ultimate Wide-Leg Jeans in pale pink, and The Ultimate Wide Leg Jeans in Tile White. I would take the crop pair if you wear loafers and the white pair for a day when the shoes can carry the colour.

 

For a cleaner end, The Wide Leg Jeans in black rinse and The Barrel Leg Jeans in Solstice keep the shape but change the mood. I would wear the black pair with a jacket, the barrel pair with a close-fitting knit, and the airy pair with a plain tee. Check the hem against your everyday shoes before deciding; denim inches have a habit of disappearing when you sit.

A straight jean should keep its line from hip to hem, even when the fit changes at the waist. The Straight Super Stretch Jeans in Deep Ocean Wash are the tidy version, with a high rise and dark indigo. The Low Rise Loose Jeans in Solstice loosen the top block and wear longer, which changes the whole proportion.

 

For a closer line, The Jules Slim Straight Leg Jeans in Concho have a mid rise and narrower ankle; The Longline Straight Leg Jeans in Clean Black are quiet and lean, good with a longer jacket. The Low-Rise Slim Jean in Greenwich fits closer up top but still finishes with a little flare, so I would not style it as a skinny.

 

The Longline Straight Jeans in Atlin are the tall, light-wash option. The Pencil Jeans in Monterey taper more narrowly, while the Jules Mid Waist Slim Straight Leg Jeans in Raebrook bring a darker wash and ankle length. The difference is not just vocabulary; rise and opening change where a shoe meets the hem.

 

I would start with the shoes I already own and try the jeans with the exact heel or sneaker I plan to wear. A narrow opening looks sharper with a slimmer shoe, while a looser straight leg can cover more of the top. What I would skip: buying a straight jean by waist size alone, then being surprised when the ankle opening changes the feel. Check the full silhouette in a mirror, not just the waistband.

A flare earns its space at the hem: too much break and it swallows the shoe; too little and it can look like a straight jean that changed its mind. The Flare Super Stretch Crop Jeans in Midvale and The Stretch Flare Crop Jeans in Osgoode both fit close through the thigh, but the darker Osgoode wash and raw edge feel sharper.

 

The Crop Flare Jeans in Coastal Blue are lighter; The Short Raw Hem Crop Flare Jeans move the same idea up the leg. The Short Crop Flare Jeans in Osgoode are another petite option, while The Vintage High Waist Flare Jeans in Rinse reach full length and widen more. I would keep the top half simple and let the hem do the talking.

 

The Stretch Flare Crop Jeans in Black Rinse fit close through the thigh and kick out at a 27-inch inseam, while Relaxed Bootcut Jeans in Solstice Wash keep the thigh straighter and open more subtly at the hem. That is the useful distinction: flares announce themselves; bootcuts quietly make room for the shoe. I would wear the full-length pairs over a heel or platform, and the cropped ones with loafers or a slim sneaker.

 

A wider hem changes the whole outfit even when the wash is familiar. When the leg opens, every shoe gets a cameo, so I would keep the top half quieter and let the line do the styling. Try the hem with the shoes you actually plan to wear, then sit down and check that it still falls cleanly.

I would decide the leg first, then the waist, then the wash. If I want movement, I would try the wide or barrel shapes; if I want a cleaner line, the straight and slim pairs make the better starting point. Flares come last, because the hem needs a shoe to make sense.

 

Then I would check the pockets and rise from the side, not just the front. The Emmy Patch Pocket pair changes the back view, and a high waist can turn a wide leg from relaxed to dressed. I would bring the shoes I wear most often into the fitting room. This is denim; the hem gets a vote. If you want to keep browsing, I also put together Zebra Pants and Taffeta Pants.