How Denim’s Baggy Fits Drive Footwear Trends

The grip that skinny jeans and ankle boots—a popular millennial pairing from the late 2000s to the 2010s—slipped during the pandemic, opening the floodgates to new Gen Z-approved styles inspired by Y2K, workwear and Western fashion. Young people eschewed the “cheugy” body-hugging jean in favor for roomy and comfortable fits like wide-leg, flare and carpenter jeans.

Millennial women are warming up to the denim industry’s looser fits despite their initial resistance.

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In March 2022, Circana published data showing that straight-leg jeans were the top-selling fit among women in the U.S., dethroning the skinny, which was the only jean style whose revenue declined in 2021 from 2019. The silhouette hasn’t bounced back either as consumers of all ages continue to follow Gen Z’s lead. Loose-fitting jeans are now mainstays in collections from 7 For All Mankind, Good American, Levi’s, Madewell, Old Navy, Universal Thread and more.

Circana, which described roomier fits such as bootcut, wide leg, and flare styles as a “bright spot” in the women’s denim business, said all were up by double-digits in 2023.

The re-introduction of these looser fits is driving millennial women to take a closer look at the rest of their closets, however.

Whereas skinny jeans and ankle boots were once the go-to uniforms on most occasions (equestrian-style boots also had their autumnal moments), the recent shift in proportions is drumming up questions this winter about what type of boots best balances the voluminous bottoms—and still looks stylish.

Even the Princess of Wales has swapped her go-to skinny jeans for kick flares.
Even the Princess of Wales has swapped her go-to skinny jeans for kick flares.

It’s a fashion query that Mandy Edwards fields at her two Jean Theory boutiques in Charlottesville and Richmond, Va. Edwards likes to to talk customers through their questions and concerns, and give them a variety of footwear options to try on. “We always have some shoes in the store for women who are unsure,” she said.

New Territory

Consumers trying out bold new jean styles are curious and eager to put their best foot forward.

TikToks tagged #widelegjeans have over 407 million views; others tagged #stylingwidelegjeans racked up 417,000 views. Vogue, InStyle and PopSugar have dedicated editorials to helping women circumnavigate the confusion. Meanwhile, fashion blogger Jo-Lynee Shane produced a visual “Denim & Shoe Pairing Guide” to pinpoint the best footwear styles for straight crop, full-length straight, bootcut/flare, cropped flare and wide-leg jeans.

Footwear and jean trends go hand in hand, said Myriam Belzile-Maguire, co-founder of the made-in-Europe leather footwear and accessories label Maguire Shoes.

“If you consider how certain fashion brands operate in both the clothing and footwear industry, their designs need to be coherent and complement each other. However, on a smaller level, I believe that pants trends would come first because of how difficult the process of selecting the right pair may be for certain people. I think people look at these trends, find a pair they like and feel comfortable with and then footwear follows.”

Indeed, footwear designers and retailers closely watch the women’s denim and bottoms categories to understand the direction they should take.

“Footwear and fashion trends often unfold in harmony, with each influencing and enhancing the other,” said Monique Rivera, Dolce Vita’s VP of design. “Typically, these trends originate from innovative styles showcased on runways or cutting-edge street style featured in editorials.”

Take, for example, the fusion of pointy-toe silhouettes paired with oversized wide-leg pants, “creating a remarkably fresh and on-trend look,” she added.

Wide-leg, flare and bootcut jeans allow for more experimentation with boots and shoes.
Street style in Berlin

Daniel Villegas, Boot Barn’s lead stylist, said the trend begins with apparel. “A pants trend will be emulated in footwear,” he said. “Sometimes a resurgence of apparel from a certain era can spark a resurgence in footwear from the same era—for example, when flares and wide legs from the ’70s came back, platforms returned and entered the conversation.”

Whereas skinny jeans are “usually paired with a bootie or something else that is sleek and not too bulky,” Villegas said there’s more creative freedom with new fits.

“With more relaxed denim styles—like straight leg, ’90s fit, dad fit, mom fit, things of that nature—there’s a little more flexibility for footwear choices,” he said. “People’s eyes aren’t immediately drawn to the boot like when they’re wearing skinny jeans, so you can experiment with footwear adorned with fringe or embellishments and just have more fun with the boot style. When you’re wearing something a little bit more relaxed, you have a wider range of boots you can pair it with.”

Boot Barn’s Idyllwind Charmed Life boot, a pointed-toe suede Western boot, offers consumers a lot of leeway for experimentation. “It’s a sleek, suede boot that comes in an array of colors. It’s also very versatile—you can tuck your pants into the boot for a more urban-cool feeling or drape them over the shaft for a more classic look,” Villegas said.

Boot Barn’s Idyllwind Charmed Life Boot
Boot Barn’s Idyllwind Charmed Life Boot

Besides boots, wider bottoms allow other footwear categories to deviate from the constraints of skinny silhouettes.

“Maybe the most obvious change is the increasing prevalence of men’s wear-inspired trends, particularly evident in the popularity of tailored footwear like slim and chunky loafers, as well as the rising trend of platforms,” Rivera said. She added that roomier denim, trousers and maxi skirts harmonize with these silhouettes and “complement the broader and more structured nature of such footwear.”

Dolce Vita Morna Oxfords
Dolce Vita Morna Oxfords

While there’s no one right or wrong style to wear with loose-fitting jeans, Maguire said shoes and boots offering a silhouette with a longer toe are in greater demand. “Since pants are longer and wider right now, it’s always nice to have the toe long enough to peek out from under,” she said.

Flare and wide-leg jeans, she said, pair well with slimmer boots like Maguire’s Salema, an ankle boot with a blade heel. “It allows the jeans to hang nicely over top,” she added. For an everyday look, Maguire suggests the Sevilla, a square-toe ankle boot with a low heel that comes in neutrals and color pops like Denim.

Maguire’s Sevilla Boot
Maguire’s Sevilla Boot

Rivera suggests choosing a pointy-toe pump, or a high heel or kitten heel for a more formal and dressy appearance. “During the fall season, a snug-fitting stretch shaft ankle boot can be an excellent choice, providing both style and comfort. For laid-back and casual days, consider a slim sole sneaker, a deconstructed loafer, or a low-heel ballet flat to effortlessly blend fashion with comfort,” she said.

What’s Next

What’s the next denim trend to impact the footwear market?

Villegas anticipates that skinny jeans will continue losing wallet share. “I think we’ll continue this path within the fashion space where there are different iterations of wide leg, loose fit, or relaxed style for quite some time in a multitude of interpretations,” he said.

Loose-fitting pants give women more room to play around with styling. With jeans that have a straight and relaxed fit, Villegas suggests fully tucking in the pants for a modern look. Or slouching the boot and half-tucking the pants, which can completely change the vibe. “Having a bit more fabric in the jeans gives us more flexibility with our design choices,” he said.

While super-oversized denim might eventually fall out of favor, Rivera said the appeal of flared and looser-legged styles should last for some time. “The shift toward a more rigid and less stretchy denim further solidifies our position within this trend, suggesting its longevity in the fashion landscape,” she said.

During the design process, Rivera said she finds someone in the office sporting looser pants to ensure compatibility, regardless of the shoe silhouette. “Looking ahead, I’m thrilled about incorporating different platform styles and enjoy seeing them paired with wider leg pants for a dynamic and fashionable combination,” she said.

“I think looser jeans will be around for the next couple of seasons, but I’m sure we will be introduced to some new styles of jeans very soon, Maguire said, adding that capri-length jeans appear to be on the horizon.

Instead of getting bogged down by trends dictated by another category, Maguire suggests aiming for balance. “I think it’s important for us to be aware of those trends and consider their impact on shoe trends and vice versa, but at the end of the day, we try to focus on designing pieces that will live outside of trends so that our clients can feel fashionable wearing them for a longer period,” she said.