18 Pairs of Soft, Stretchy Jeans That Feel Like Leggings

J.Crew Factory’s fitted jeans gives us Beyoncé levels of confidence when we walk down the street—even the runway-like streets of Paris or Milan. Classic, versatile, comfortable, high-quality…we can sing the praises of this pair all day long. The secret to their amazing fit is the skinny design that’s fitted through the hips and thighs, but not too snug in the calves.

“These jeans are possibly the most comfortable that I’ve ever owned,” is just one of the dozens of Nordstrom reviews raving over Paige’s cute, cropped boyfriend jeans. Between the relaxed cut and the extremely soft cotton/polyester material with a jot of elastane, this dark-wash style honestly feel like wearing jersey sleep pants, not jeans. Just be sure to size down.

With more flare than slim or straight-leg jeans, but not as much as full-on bell bottoms, bootcut jeans are a classic for their sleek silhouette that just happens to look amazing with heels (and yes, boots—especially those with higher heels). Women who find the fit of bootcut jeans tricky to pull off report that this version from Madewell actually flatters, thanks to the slimness throughout the thighs and the cropped hem. Many owners suggest sizing down, and note that the organic stretch cotton fabric here has a little less give than other picks on this list, but it breaks in perfectly after a few wears.

Wherever you fall in the great to-wear-or-not-to-wear-white-after-Labor-Day debate, this pair of classic white bootleg is a keeper, all year round. Not to get too technical but the fabric is made of 20% Lyocell, which gives them an incredible softness, plus 3% spandex, which makes them form-fitting (but not super tight) in the hips and thighs. As with other bootcut styles, these look best with at least a one-inch heel.

If Uniqlo were to discontinue this mega-stretchy pair of jeans, we’d freakin’ lose it. The Japanese casual-wear brand states that their Ultra Stretch Mid-Rise Jeans are made from the world’s stretchiest denim, and we’re inclined to buy into that bogus-sounding claim (this writer spent her pregnancy in her Uniqlos). Their waistband hits the belly button line to safely tuck in areas you don’t necessarily want on display, and though their cut is super-skinny, it’s not in a stop-your-blood-circulation kind of way, thanks to impressively elastic fabric.

The problem with some skinny jeans is that they are too skinny. You know what we’re talking about—the ones where wiggling into them is a full-body workout that eats up like all of your morning prep time. (Especially not cool when Amsterdam or Prague is out there waiting to be explored!) Kut from the Kloth’s Donna skinny jeans won’t do you like that, we swear. The style fits snugly but not so close as to cut into your stomach or leave stitch marks on your skin. Instead, the cotton-based denim has a bit of spandex for stretch and support. PS: Size down with this style.

If you still haven’t jumped on the normcore bandwagon, here’s your chance to bound onboard and never look back. With a super-high waist and a straight leg, Everlane’s Cheeky style definitely oozes a mom jeans vibe, but not in a baggy 80s kind of way. They have just a little bit of stretch—2% elastane mixed with premium Japanese denim—for a comfy fit that won’t lose its shape as you wear them day after day (which we guarantee you will).

Just the thought of wearing these Gwyneth-esque wide-leg jeans makes us want to bike down a beach boardwalk or swing by a farmers’ market for fresh corn and flowers. The point is: these high-waisters are pure summer. Cut from stretchy denim that hugs your hips before flaring down, these cropped cuties from Madewell are our favorite jeans for warm weather.

If it seems like scrolling Instagram lately comes with a side of major deja vu, you’re not mistaken. Supermodels and fashion influencers are dressing like it’s 2000 again and it’s all because of low-rise jeans. So if you want to relive the early aughts, this is your (and probably your midriff’s) time to shine. Naturally, you should style these babies with your favorite tube top. Belly chains and newsboy caps optional.

Distressed detailing, an undone hemline, and a mid-rise silhouette give these so-called mom jeans a cool downtown vibe. Their 1% spandex may sound skimpy, but for a pair of loose-fitting jeans, it’s plenty—enough that when you sit down or squat, they won’t dig into your skin.

If Kate Moss is your style icon, Brit rock is a regular on your Spotify playlists, and a trip London is on your calendar, then you need these jeans in your life. With just the right amount of distressed accents, they fall in the stylishly edgy category rather than the I-went-overboard-with-the-scissors-while-trying-to-DIY-an-old-pair-of-skinny-jeans one. We also love the slightly fringed hemline—a detail that has been getting some celebrity endorsement in the past year.

The 80s are calling and you better answer! These high-rise jeans sport the coolest peekaboo dip-dye wash; pair them with a longer top when you want to mix up the look. Just don’t reach for the crimper when you put them on—we need to draw the line somewhere.

The problem with some straight-leg jeans is that they fit loosely in the hips, which many women find rather unbecoming. That’s not the case here. With these super-soft jeans from Joe’s, you still get the comfortable fit that the stretchy denim (cotton blended with modal and elastane) and straight legs provide without the awkward and unflattering look on top. 

There’s a reason why the Jamie is one of Topshop’s best-selling jeans. Its high-waist skinny silhouette is very flattering on petite figures and once you style the jeans with heels, it all falls into place. Bonus points for the soft-as-all-get-out stretchy denim that literally makes them feel like leggings.

A pair of slightly bootcut jeans hugs your silhouette nicely before ending in a slight flare that stops short of bell-bottoms territory. If you want the legs for days look, opt for a full-length pair (as opposed to ankle-length or cropped), like Curvy Bootcut Jeans from Loft; pair them with a blouse (tucked into the high waist) and block heels.

Maternity clothes don’t have to be sacklike, unflattering, out of step with current trends, or some combination of the three. Expectant mothers can tap into the cropped bootcut look with AG’s Jodi Jeans, whose thick denim provide just the right amount of stretch and support. 

For jeans that won’t sink your bank account or introduce questionable quality into your closet, look no further than this affordable pair of skinnies from Hontoute. We’ll start by saying: this pair is flattering! Not just oh-you-look-cute flattering, but OMG-who-makes-those-jeans-from flattering. The stretchy fabric and butt-lifting high-waist construction are to “blame” for this. There are six shade options available and we intend to add every single one of them to our closet.

The Paige textile team has managed to create a fabric blend that stretches juuust enough to hug (ie, support) your body without being super-tight or stretchy to the point of losing its shape. You can quote us on this one—you will have the brand’s Transcend Skyline Skinny Jeans for years to come and they will look like new each time you put them on (which will be every day).