Style & Beauty

Jean And Boot Pairings: How To Match Fall's Most Popular Trends

Wondering what to wear with your cropped jeans and flares? A stylist has the answers.

Finding the perfect pair of denim in a sea of must-have trends can be overwhelming, especially with the wealth of new styles hitting the racks and online shopping marketplaces ― flared, skinny, cropped, bootcut and high-waisted seem to be the go-tos this season. But when you add another step to the process and pair them with boots, how does one find their perfect pairing of silhouettes?

To get a better understanding of how to pair denim and boots, we enlisted the expertise of former BCBG fashion buyer-turned-celebrity stylist, Thanda Gibson.

So what’s the secret to matching denim with the right footwear? “Balance is key,” Gibson said.

“To maintain this balance, I find it best to pair cropped denim with a boot that is tall enough to cover your exposed leg to elongate the leg,” she said. “If the boot is too short and your leg is showing, it can cause your legs to appear short and stubby.”

Cropped denim may be an intimidating trend, but that’s no reason to shy away from it.

“We all can embrace trends,” Gibson said. “Fashion shouldn’t be limited to just a few body types. However, it is important to learn your body type and tweak things a bit to best flatter your figure.”

“For instance, if you are petite, I would try pairing your cropped denim with a block-heeled bootie to add a bit of height to your overall look,” she continued. “For a curvy physique like myself, I like to choose a cropped sweater for fall. Or try a long-sleeved bodysuit to keep your figure balanced and avoid creating a boxy silhouette.”

If you’re still unsure about how to mix and match your denim with your fall footwear, here are a few general rules.

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Cropped Jeans + Narrow Boots

With cropped denim, Gibson recommended “going for a narrow boot that is a bit elevated with a small heel, keeping the cropped denim from looking too boxy on the legs, helping to give the silhouette some shape and dimension.” A mid-calf version makes for the ideal height, she said.

Flared Jeans + Square Toe

“Try a square toe with a flare jean this season,” Gibson said. “There are plenty of options out there at the moment.” She suggested pairing 1970s-era pants with “a Western-style square toe with a metal tip to keep it fresh and new.” You can go as low or as high as you would like, from ankle to knee.

Slouchy Jeans + Ankle Booties

Slouchy bottoms may seem right for select body types, but look for a high-rise option that defines your waist. Gibson recommended try an ankle bootie to tie your look together, noting, “A closed-toe mule is great as well, since it’s boot-adjacent.”

Additionally, go for a slight cuff on your jeans when pairing them with ankle booties.

“No need to make it perfect, just a slight roll,” she added. “I would stay away from a thick cuff, as this is usually not flattering on the leg.”

Wide-Leg Jeans + Metallic Boots

With wide-legged denim, Gibson pointed out, “There can be a lot of fabric, and a pointy toe ― especially an exaggerated one ― really helps to bring balance. Try going for a bit of a pop, with white or maybe a metallic-like silver.”

Whatever you do, just don’t tuck your jeans into your boots.

“I wouldn’t recommend tucking a wide leg into a boot,” Gibson said. “In most cases, this will look sloppy and not flattering.”

Skinny Jeans + Knee-High Boots

The skinny jean has a longstanding history as a go-to silhouette, but that doesn’t mean you can’t teach an old jean new tricks. Try a pair of knee-high boots, since “knee-high boots work great with skinny jeans,” Gibson said. There are many great options to choose from the season, but Gibson favors an “’80s slouchy knee boot or patchwork boots.”

Gibson’s final tip: Invest in a “neutral snakeskin-embossed knee high or calf boot.”

“You can pair it with everything, but it adds a bit of texture and dimension that your black boot is lacking,” said Gibson, adding that, “they will work with cropped, straight and wide-leg jeans. Thank me later for how often you reach for them this season.”

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