What Happened When I Put Gap's Most Popular Jeans to the Test
From Hailey Bieber's much-discussed baggy style to familiar favorites, here's what stood out.
I practically live in denim, especially during the colder months. My autumn wardrobe is filled with everything from slim-fit cigarette jeans to wide-leg styles, many of which I’ve shamelessly worn into the ground. Fraying hems, faded indigo washes, and the occasional loose button are proof.
In need of a refresh, I turned to Gap’s latest fall denim collection, which has no shortage of options.
During a recent visit to Gap’s Flatiron store in Manhattan, I found an entire section devoted to denim. Jeans were stacked nearly to the ceiling and neatly folded across display tables, with seemingly every silhouette, size, and wash represented. Naturally, I made a beeline for the Hailey Extra Baggy Jeans, which debuted in collaboration with Hailey Bieber earlier this year. The style has been generating plenty of buzz, and I was determined to see what all the fuss was about. (Spoiler: I left with a pair.) There were also familiar favorites, including Gap’s High-Rise Stride Jeans, a longtime staple of the brand’s denim lineup.
Jane Pattinson, Gap’s SVP and Global Head of Design, says that range is precisely the point. “Denim is personal, so versatility in our assortment is crucial,” she tells me. “We aim to offer newness in silhouette and proportion while always refreshing the iconic styles our customers know and love.”
I tried on several pairs, each with a slightly different fit and feel. Some were relaxed and slouchy; others had a more tailored shape. Styled with simple tees, knit sweaters, and structured jackets, they gave me plenty of ideas for getting dressed this fall. More importantly, I found a few pairs worth making room for in my already denim-heavy closet.
Ahead, the Gap jeans that caught my attention and how I plan to wear them this season.
The Hailey Extra Baggy Jeans
At five-foot-four, I was admittedly worried that these baggy jeans would overwhelm my frame. Instead, the roomy silhouette had just enough structure to feel flattering without losing that relaxed, oversized look. I initially reached for a size 28 but ended up sizing down to a 27, so I'd recommend going down a size if you're between sizes.
To balance the proportions, I'd pair the Hailey Extra Baggy Jeans with a fitted crewneck T-shirt and a cropped jacket. It's an easy combination for weekends when you want to look put together without trying too hard.
The High-Rise Stride Wide-Leg Jeans
Gap’s High-Rise Stride Wide-Leg Jeans come in 15 different washes (yes, 15!), but I was immediately drawn to this deep indigo shade. The dark wash feels a little dressier than traditional blue denim, which suits my tendency to lean toward more tailored looks.
For styling, I wanted to introduce some color, so I paired them with Gap’s CashSoft Crew Sweater in a vibrant shade of cherry red. Layered over a plain white T-shirt, the combination felt like an easy way to bring a little personality to a classic fall outfit.
The Mid-Rise Straight Taper Jeans
The Mid-Rise Straight Taper Jeans are one of Pattinson’s favorites from Gap’s fall denim collection. “This style offers a balanced, slightly tapered silhouette for a polished yet effortless look,” she says.
That slightly tailored shape is exactly why I’m adding these jeans to my workwear wardrobe. I can already picture wearing them with a crisp button-down and a cardigan draped over my shoulders for an office outfit that feels relaxed but still considered.
The Low-Rise '90s Loose Jeans
Can I let you in on a secret? I’ve been avoiding low-rise jeans since high school. The waistline always seems to slip below my hips, leaving me feeling overexposed and uncomfortable. So imagine my surprise when I tried on Gap’s Low-Rise ’90s Loose Jeans and found that they offered just the right amount of coverage without sacrificing the relaxed fit.
Leaning into their vintage appeal, I paired them with a retro-inspired leather bomber jacket featuring a funnel neck and ribbed hem. The combination has an easy ’90s feel without looking like a costume.
The Mid-Rise Split-Hem Relaxed Straight Jeans
As the name suggests, these jeans are all about comfort. The relaxed, straight-leg fit offers plenty of room to move, while the cotton-stretch blend feels especially soft.
They're the kind of jeans I'd reach for on busy days when I'm constantly on the go. Add a cozy barn jacket and a pair of comfortable shoes, and you've got an easy fall uniform you'll want to wear on repeat.
