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Live the Gossip > Lifestyle > My Mom, 52, and I, 28, Always Fight Over Who Has the Comfiest Jeans — These Are Our Top Fall Picks from $53
Lifestyle

My Mom, 52, and I, 28, Always Fight Over Who Has the Comfiest Jeans — These Are Our Top Fall Picks from $53

Written by: News Room Last updated: September 9, 2026
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Including straight-leg and relaxed styles

Credit: Nordstrom (1)

The Most Comfortable Jeans for Fall

My Picks

  • Madewell The Perfect Vintage Wide-Leg Jeans, $148; Madewell
  • Gap Barrel Jeans, $53 (orig. $90); Amazon
  • Everlane The Low-Key Jeans, $67 in cart (orig. $168); Everlane
  • Abercrombie ’90s Relaxed Jeans, $90; Abercrombie

My Mom’s Picks

  • Kut from the Kloth Catherine Boyfriend Jeans, $67 (orig. $80); Amazon
  • Good American Good Legs Straight-Leg Jeans, $98; Nordstrom
  • Mother The Kick It Straight-Leg Jeans, $167 (orig. $278); Nordstrom
  • Maeve Colette Cropped Wide-Leg Jeans, $118; Anthropologie

I go to my mom for advice on everything from skincare essentials to packing tips, but the one category we can never agree on is jeans. 

For the past two years, my mom has failed to persuade me to swap my tried-and-true denim brands for her supposedly “superior” picks. Where I’m a fan of loose, relaxed styles, she prefers a more form-fitting look you can cuff. I also prefer a slight stretch whereas she appreciates compression. We each believe we’ve found the comfiest jeans, but we’ll let you decide who’s right. 

Keep reading to shop our favorite styles from brands such as Gap, Good American, Mother, and Madewell. 

Related: A Stylist Says These 4 ‘Timeless’ Fall Staples Can Create Endless Outfits — Build Your Capsule Wardrobe from $18

Madewell The Perfect Vintage Wide-Leg Jeans 

Credit: Madewell
Credit: Madewell

$148 at Madewell.com

I worked at Madewell for two years, so I’m a self-proclaimed expert on the brand, especially its jeans inventory. My best argument? The material holds up over time. I have pairs from six years ago that look and feel brand new. Every time I wash them, they grow softer and the slight stretch lets them gently form to my body. 

Gap Barrel Jeans 

Credit: Amazon
Credit: Amazon

$90 $53 at Amazon

My least favorite jeans are the ones I can’t squeeze past my thighs, which is why I look for pairs with extra room in the legs. Gap’s barrel jeans provide that feature without swallowing my short frame, as some wide-legs jeans do. The material isn’t overly rigid and the rip-free design makes these jeans easy to dress up with a button-up shirt and ballet flats for the office.

Kut from the Kloth Catherine Boyfriend Jeans 

Credit: Amazon
Credit: Amazon

$80 $67 at Amazon

My mom always tells me to try Kut from the Kloth jeans — she even tried sneaking a pair of hers into my suitcase during a recent visit. She likes how “certain areas [are] compressed”, including her stomach, for a smoother look. The jeans also have stretch, but not so much where it feels like everything is on display. A boyfriend fit is one of her go-to silhouettes because it’s slightly loose without feeling baggy.

Good American Good Legs Straight-Leg Jeans 

Credit: Nordstrom
Credit: Nordstrom

$98 at Nordstrom

This is one of those brands that makes my mom feel “excited” to wear her jeans. For her, a good pair of denim should be comparable to sweatpants — comfortable enough to wear for long periods of time, but put together enough to leave the house in. She’s been gravitating towards straight-leg denim ever since skinny jeans became “outdated” because they make her appear taller and rarely feel constricting.  

Refresh your denim collection with our favorite jeans, and keep reading for more options we love starting at $67. Then let us know who persuaded your purchase in the comments!

Everlane The Low-Key Jeans

Credit: Everlane
Credit: Everlane

$169 $67 at Everlane.com

Abercrombie ’90s Relaxed Jeans

Credit: Abercrombie
Credit: Abercrombie

$90 at Abercrombie.com

Mother The Kick It Straight-Leg Jeans

Credit: Nordstrom
Credit: Nordstrom

$278 $167 at Nordstrom

Maeve Colette Knit Wide-Leg Cropped Jeans

Credit: Anthropologie
Credit: Anthropologie

$118 at Anthropologie

We independently evaluate all recommended products and services. If you click on links we provide, we may receive compensation.

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