Time for a Re-Boot! – Bootcut Jeans Are the Y2K Inspo You Need Now

Move over skinny, there’s a new silhouette in town. But these aren’t the aughties versions you wore in school. We’ll show you 15 fantastic bootcut jeans, updated and ready to rock for your Summer/Fall

Oops, we did it again. It was bound to happen, really. Following the return of the Y2K jewelry obsession, the micro mini and the tuck-under-your-armpit crescent bags, that darling apparel item of the aughties, the boot cut jean, was the obvious next choice.

That’s not to say today’s versions are a total rinse-and-repeat of the originals. It’s 2022 after all. This season’s version of the boot cut include lots of advanced materials that are both more comfortable (stretch and performance fabrics) and made with better practices in place (recycled materials, fair trade labor practices, working wages, etc).

With all that in mind, let’s show you fifteen fab boot cut jeans as picked by our editors, ready to add some fresh back into your S/F wardrobe.

Let’s start strong with these dark wash beauties that understood the assignment completely. Premium denim adds a touch of stretch to support you in all the right places, courtesy of a proprietary slimming panel with a patented criss-cross design. It gives your bootie a little lift while keeping things sleek in the front. Extra points for the dark azure blue that easily transitions from baby tee & platform shoe casual to crisp white button down + heels office fit. Did we mention it comes in Reg/Tall/Petite options as well as sizes 00 to 18? Seriously, why aren’t these in your closet already?

NYDJ, Barbara Bootcut in Rinse $99


Looking to go all in on the retro look? Here’s your trifecta: hip-hugging inseam, whisker-washed denim and of course, the super-stitched, horseshoe pocket branding from the one-and-only OG…True Religion.

True Religion, Joey Super T Stitch Jeans $179.25


Fun fact: black denim jeans were never more popular than in the aughties…at least so far. These mid rise, durable black denim bootcut jeans are made with stretch fabric up top, giving a fitted look through the hip and thigh, with a relaxed opening through the leg. What else to love? How about deep, full sized pockets you can actually fit things into? Also, they come in sizing options from 00 all the way up to 40 (that’s a 7x).

Universal Standard, Marne Bootcut in Black $98

Full length boot cut isn’t the only version seeing a resurgence. The bootcut capri has also been gaining traction, especially in these warmer summer months. These capri length lowrise fellows are the perfect example. The medium true-blue color makes them a versatile option for day or night. Shoewear is key to pulling this look off right. Square toed booties, flatform sneakers and stacked heels look absolutely best with this jean.

Paige, Sloane Crop Bootcut $229


Still hoping to score that perfect pair of white denim that’s comfortable enough to wear in summer’s heat and stylish enough to take you into fall? Look no further than these slim bootcut ankle jeans. They’re made with a moisture-wicking Cool Embrace® Denim by NYDJ. The fit is slim but with a touch of Lycra woven in, you’ll be moving easy and feeling chic. Comes in a really nice range of sizes from 00 to 28W.

NYDJ, Slim Bootcut Ankle Jeans in White $119


Don’t like the idea of anyone else having your exact jean? These patchwork bootcuts are made from all recycled denim and are crafted together individually, so no two are exactly alike. Definitely a show-stopper and they normally retail for much more, but lucky you! We found them on sale at a price that’s just as stunning as they are.

RE/DONE, 60s Patched Bootcut $195 (reg. $650)


If raw hems are your thing, these dark wash indigo jeans are for you. With a midrise inseam that hits just above the hip bone, they’ll look fantastic with any cropped top you have in your wardrobe rotation right now. Ditto for your micro cardigan.

rag & bone, Peyton Mid-Rise Bootcut $255


If you prefer your bootcut a little more on the conservative side, but still crave that wow factor, these pretty paisley-patterned jeans will do the trick. Barely there flare at the bottom with a loose fit, these are a welcome edition to your fall fits.

The Kooples, Faded Paisley Pattern Crop $125


They call them green jeans, but not for the color. These high rise, slim bootcut jeans are made of over 25% recycled cotton and elastane. And when they say this is a retro look, they mean it…they’ve been outfitting professional cowgirls since 1947.

Wrangler, Retro Green Jeans $79


Feeling the need for a little destruction in your bootcuts? These high rise jeans have just the right amount of distress and with over 2% of spandex they have a fitted look with easy movement.

Lucky Brand, High Rise Bianca Bootcut $50


These lemon-lime colored crops are super faded and made with a vintage stretch fabric that feels super soft. Ideal for those summer days but they’ll look just as chic with your fall booties and chunky sweaters.

Joe’s Jeans, The Callie Highrise Cropped Bootcut $188


Not everyone is a fan of the fitted. If you’re favorite thing about the aughties look leaned more towards the skater vs the skinny, these jeans will have you in your happy place. High rise inseam with a looser fit throughout, and because they’re cropped you’re free to show off your Vans to all the world.

Hudson Jeans, Blair Starry Night Bootcuts $89.99


So how low can you go? Well these leggy lovelies from Balmain are not for the torso-timid. With a super low rise they hit just under the hip bone, making them all but ready for you to sport your whale tail.

Balmain, Black Bootcut Jeans $525

Not interested in embracing the full whale tail? Designers understand, which is why these next jeans give the illusion of the ‘peeking undies’ without the real deal. With cutouts in the front, you can have your peek-a-boo and you’re demure too.

Good American, Good Boy Bootcut Jean $47.99

And for our last pick, well it wouldn’t be truly a trip down the aughties path without paying homage to those bedazzled patterns that literally took over the jean world for over half a decade. They can be a galvanizing look. But this pair we found takes these embattled embellishments and gives them a cool boho twist.

Johnny Was, Westside Baby Bootcut Jeans $111.99

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