Welcome to Jeans Month on the Strategist, where we’re obsessively vetting denim — from trying on every pair at the Gap to asking dozens of stylish people about their favorite fits. For more, head to our Jeans Month hub.
Contributor Erika Veurink, who’s six-foot-two, and our newsletter editor Ashley Wolfgang, who’s four-foot-eleven, look for very different things in a pair of jeans. Erika hunts for a long inseam (36 inches, ideally), while Ashley searches for a 25-inch one (and often takes jeans to the tailor for hemming). Erika, who wears a size 6 or 8 typically, prefers her jeans with a straight or wide leg, while Ashley, who wears a size 0 or 2, likes her jeans on the tighter, slimmer side (“skinny jean habits die hard,” she says). So we sent them both to Gap to try on eight pairs of in-stock jeans to see how they really fit on a variety of body types.
The Mid-Rise Baby-Boot Jean
Cut: Baby boot | Lengths: Petite 27.5” (67.5 cm), Short 28.5” (72 cm), Regular 30” (76 cm), Long 32” (81 cm), Tall 34” (86 cm) | Rise: Mid | Material: 84% Cotton, 7% Recycled Materials, 9% Stretch | Fly: Zip | Washes: Dark Wash, Light Indigo
Erika: A baby boot cut was an unlikely pair for me, since, as all tall girls know, even the slightest flare can come in inches too short. I was pleasantly surprised by the length of this pair and found the mid-rise to be very comfortable. They’re made from 84 percent cotton, 7 percent recycled materials, 9 percent stretch fabric, which felt stretchier than the 100 percent cotton I’m used to and a lot more comfortable off the bat. The shape and stretch felt a little 2010s, but not in a bad way. I’d take these true to size.
Ashley: This jean was a ghost of denim’s past for me. The baggy, bunched up bottoms brought back a visceral memory of the back of my jeans bottoms getting soaked and ripped up from walking outside in Minnesota winters during the early ’00s. That said, they fit me quite well overall. The petite style has a 27.5-inch inseam, which, again, was a tad too long for my legs, making the boot cut lean on the baggier side. The 24 size fit me perfectly and because these were a bit stretchy, they made the mid-rise a bit more forgiving.
The High-Rise Stride Seamed Wide-Leg
Cut: Wide-leg | Lengths: Petite 29” (74 cm), Short 30” (76 cm), Regular 32” (81 cm), Long 32.5” (83 cm), Tall 34” (86 cm) | Rise: High | Material: 99% Regenerative Cotton, 1% Stretch | Fly: Zip | Washes: Medium Indigo
Erika: I take my denim plain, usually, so it’s fair to say a braided-belt detail isn’t my cup of tea. Overall, these jeans are trend forward, which doesn’t always translate into a tall variation. For example: The faux let-out hem feels kind of goofy when the hemline is short. They feel a lot stretchier than the 1 percent percent elastane they’re made from. But the Washed Black wash feels way cooler and less obvious — more like a flared jean you might have held on to from 2013.
Ashley: I felt like I was drowning in this pair of jeans. The petite length — which has a 29-inch inseam — dragged well past my feet and the wide-leg style looked much baggier than it does on the model on the site. The size 24 felt great in the waist, but it did have a bit too much extra fabric in the crotch area that bunched up when I sat down. Although these didn’t fit my level of petite, if you’re closer to five-foot-three or five-foot-four, I think they might work.
The High-Rise ’90s Straight Jeans
Cut: Straight | Lengths: Short 29” (73.5 cm), Regular 30.5” (77), Long 32.5” (82.5 cm) | Rise: High | Material: 83% Cotton, 11% Polyester, 5% Recycled Cotton, 1% Stretch | Fly: Zip | Washes: True Black, New Off White, Medium Indigo, Dark Indigo, Light Indigo
Erika: It’s tough to find a jean that approximates a true vintage style well. My advice is to hunt for these jeans at places like the Gap, where the vintage pair you’re really hoping to find might have originated. True to their ’90s name, these jeans have a good high rise. They have very flattering back pockets and a length that feels impressive for Gap. The whiskering on the thighs isn’t my favorite, so I’d opt for washes like Dark Indigo or True Black to get as close to the real (vintage) thing as possible.
Ashley: These were my perfect pair. The 26-inch inseam on the petite fit hit right past the ankle and the straight style of the leg felt true to size, as opposed to the much (unintentionally) baggier pairs I tried on at the store. These also fit perfectly at the waist, while being a bit on the snug side (which I don’t mind). I did try a size up in the 25, but it brought back the baggy problems I had with other pairs, so went back to the 24 and took them home with me.
The Mid-Rise UltraSoft Baggy Jeans
Cut: Baggy | Lengths: Petite 28.5” (72 cm), Short 29.5” (75 cm), Regular 31” (79 cm), Long 33” (84 cm), Tall 35” (89 cm) | Rise: Mid | Material: 55% Cotton, 40% Tencel, 5% Recycled Cotton | Fly: Zip | Washes: Ecru Beige, Medium Indigo, Light Indigo, Rinsed Indigo, Black, Green Camo, Straw Yellow, Twig Green, Terra Brown Light Wash
Erika: I don’t want to play favorites, but I kind of have to with these Gap Baggy jeans. They’re pretty close to the comfort level of sweat pants but actually look nice enough to wear out and about. Get your true size to make the most of the bagginess or size down if you want something a little tighter on the hips. My favorite washes were the Ecru Beige and Optic White, which I’d pair with a plain white T-shirt and your coolest sneakers.
Ashley: With a 28.5-inch inseam, these were very long for a short/petite jean. Like the name suggests, these were baggy all around. So baggy that even the waist felt oversize to me. I tried on the 24 but could have sized down to a 23 or 22 if they offered them. Fabric-wise, these felt more like a pair of sweatpants I would lounge around in or wear to do errands if I wanted to be comfy but still look nice (perhaps they’re the modern-day jegging?).
The High-Rise Horseshoe Jeans
Cut: Horseshoe | Lengths: | Rise: High | Material: 95% Cotton, 5% Recycled Cotton | Fly: Zip | Washes: New Off White, Black, Rose Mist Pink, Dark Blue Indigo, Light Tint, Medium Indigo, Light Indigo
Erika: My expectation was to hate these jeans (horseshoe, really?). But slipping into these strange little pants, I felt a smug sense that I was being proved wrong. They’re too short for me, but to be clear, I’m six-foot-two. On an average tall person, these would crop quite nicely. They’re soft and snug on the bum but loose in the leg, which can be hard to find. I was impressed by the Dark Blue Indigo wash, which was a very good vintage impression. Bravo, Gap. Horseshoe it is.
Ashley: With an inseam of 27 inches, these were the shortest of the bunch so far and the hem just grazed my foot. I’m sure these would be a great cropped style on someone much taller, but this pair looked comically overproportioned on me. Looking back at pictures, the seams around the knee also make it look like my knees are bent (they are not). Compared to the other styles I tried, the waist on these was a tad looser and didn’t do much for my figure (other than remind the world how short I am).
The High-Rise Barrel Jeans
Cut: Barrel | Lengths: Petite 27” (68.5 cm), Short 28” (71 cm), Regular 29.5” (75 cm), Long 31.5” (80 cm) Tall 33.5” (85 cm) | Rise: High | Material: 95% Cotton, 5% Recycled Cotton | Fly: Zip | Washes: Dark Rinse, Black, Medium Indigo, New Off White, Riverbed Brown, Mesculen Green, Classic Khaki Tan, Light Indigo, Flannel Taupe Beige
Erika: Now’s the time for me to get candid. I hate barrel jeans. I just have a prejudice against them, and even the best barrel jean in the world couldn’t convince me otherwise. These are my least favorite jeans I tried on, not only because the distressing hit me at mid-thigh instead of my knees but because I so preferred the understated shape of the High Rise ’90s Straight Jeans or the High Rise Horseshoe Jeans. Commit in one direction.
Ashley: Less exaggerated than the Horseshoes, these also had a 27-inch inseam and fit pretty similar to the Horseshoe jean in the length and rise. The fit overall just looked baggier than in barrel. I’m not opposed to the horseshoe fit in general, but have yet to try a pair that don’t make me look shorter than I am.
The High-Rise ’70s Flare Jeans
Cut: Flare | Lengths: Petite 30” (76 cm), Short 31” (78 cm), Regular 32” (81 cm), Long 34.5” (88 cm), Tall 36.5” (93 cm) | Rise: High | Material: 86% Cotton, 13% Recycled Materials, 1% Stretch | Fly: Zip | Washes: Medium Indigo, Dark Wash, Dark Indigo, Medium Wash, White, Medium Indigo
Erika: Tall flares are hard to find. These, in fact, proved that age-old conundrum true by clocking in at a few inches too short, but as mentioned, maybe you’re “regular” tall and could pull these off. They’re stretchy enough that you could size down for something sexy. I’d go for the darkest wash possible to keep them from looking too trendy. There’s no hem to let out here, so it’s important to try these on if you’re anywhere above six feet tall.
Ashley: These were perfect flares. They hit me in all the right places from the waist, butt, and through the thigh and knee. With a 30-inch inseam they were the longest of the bunch, though, but after our social-media editor Kathy genuinely suggested I try cropping them, I fell in love. Seeing how these would look cropped felt flattering and complemented my height without overwhelming my leg. I will be taking these to my tailor!
The High-Rise True Skinny Jeans
Cut: Skinny | Lengths: Petite 24.5” (62 cm), Short 26.5” (67 cm), Regular 28” (71 cm), Long 31” (79 cm), Tall 33” (84 cm) | Rise: High | Material: 81% Cotton, 13% Recycled Materials, 6% Stretch | Fly: Zip | Washes: Dark Wash, Medium Indigo, Indigo Destroy
Erika: As a Gen-Z cusp, I know I’m supposed to embrace skinny jeans, but I’m leaning into my millennial side by side-eying these jeans. They’re stretchy, which you’d want in a skinny jean, hypothetically, and very high waisted. They’re also a little on the shorter size, and when I bent over I noticed a bit of gaping in the waist because of the stretch. My suggestion? Size down in the High Rise ’90s Straight Jeans instead.
Ashley: I tend to like jeans more on the fitted side, but I thought I’d sworn off skinny jeans once I was past my emo phase. I have to admit, though, these fit pretty well. There’s a reason why so many short people wore them for so long. These ones from Gap had the shortest inseam of the bunch (24.5 inches) and hit me right at the ankle. They also had just the right amount of stretch in them that felt comfortable and not restrictive.
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