Kendall Jenner’s Footwear Evolution: From Rugged One Teaspoon Boots to Minimalist The Row Sandals

Whether navigating London’s avant-garde fashion circuit or a high-profile Miami wedding, Kendall Jenner’s style evolution is defined by a “footwear-first” philosophy.

By prioritizing bold, runway-inspired silhouettes over traditional dress codes, Jenner has mastered the art of the visual statement.

This time, we examine two defining looks from 2021 alongside a formative 2015 outfit, tracing how Kendall Jenner uses footwear—from the rugged utility of One Teaspoon boots to the “naked” minimalism of The Row—to anchor her style, before concluding with links to her most recent and standout shoe moments.

Footwear as Provocation: Kendall Jenner’s Mônot Cutout Wedding Look

In November 2021, Jenner sparked a significant fashion debate when she attended the wedding of Lauren Perez and David Waltzer in Miami. For the reception, she opted for a daring diamond-cutout two-piece maxi dress from Eli Mizrahi’s contemporary label, Mônot.

While she wore a traditional blue silk bridesmaid gown for the ceremony, the reception look became a lightning rod for social media criticism.

Via Kendall Jenner’s Instagram: Kendall wears a Monot diamond-cutout two-piece maxi dress as she takes bathroom selfies with Hailey Bieber, Bella Hadid, and Jesse Jo Stark

Critics labeled the avant-garde piece “unequivocally inappropriate” for a wedding, questioning the etiquette of wearing such a provocative silhouette to a friend’s nuptials.

Despite the controversy, the dress has since become a collector’s item, cementing its place in the Jenner style canon. Here’s what some Instagram users had to say:

“I love Kendall, but is she in love with the groom or something?”

“Wow, completely inappropriate for a wedding.

“Sheesh. At a wedding? The dress is a moment but not a moment to be had at someone else’s wedding.”

“It’s hard to believe she is friends with the bride if this was the outfit she went with.”

Minimalist Grounding: Zebra Prints Balanced by The Row Sandals

For another segment of the Miami wedding weekend, Kendall leaned into a sophisticated animal-print aesthetic.

She was photographed wearing a painterly zebra-print Dundas midi dress, showcasing a more refined version of her “bold and adventurous” style.

Kendall Jenner styles a painterly zebra-print Dundas midi dress with minimalist black The Row Bare sandals, finishing the look with a sleek By Far Rachel shoulder bag (Credit: MEGA / WENN)

The brilliance of this look was in the minimalist grounding; she styled the busy print with “Bare” sandals and a “Rachel” bag, both from The Row.

This choice showed how Jenner uses understated footwear to balance loud, graphic patterns, maintaining an air of effortless luxury even amid high-profile peers like Hailey Bieber and Bella Hadid.

Kendall Jenner grounds the bold zebra-print Dundas dress with The Row Bare sandals, choosing their near-invisible straps to keep the focus on clean lines, ease of movement, and an understated luxury finish suited to a Miami wedding setting on November 12, 2021 (Credit: MEGA / WENN)

Kendall Jenner was joined by longtime friends Hailey Bieber, Bella Hadid, and Los Angeles–born Arab model Fai Khadra at the Miami wedding, with Hadid drawing particular attention in Andrea Wazen Mandaloun sandals styled with a Prada skirt and a refined mix of diamond and gold jewelry.

Kendall Jenner balances a zebra-print slip dress with minimalist black sandals, while Bella Hadid sharpens her patterned co-ord with lace-up stiletto heels as they step out with Fai Khadra for a Shabbat dinner in Miami (Credit: MEGA / WENN)

While Kendall gravitated toward restrained minimalism, Hailey Bieber leaned into sharper evening glamour, grounding her sleek leather silhouette with delicate, lace-up stiletto heels that added precision and lift to the look.

Hailey Bieber wears a strapless midi Magda Butrym dress with FEMME LA sandals, an Anita Ko Zoe necklace, and a Saint Laurent bag (Credit: MEGA / WENN)

Kendall Jenner’s preference for clean, minimalist footwear often leads back to The Row. Your Next Shoes has documented her off-duty looks in The Row Adam loafers paired with the Margaux bag, as well as her tailored Paris Fashion Week styling in The Row Enzo loafers worn with sharp suiting.

Even outside of footwear, the Olsen-founded label remains a constant in her wardrobe, from accessories like The Row Banana bag, spotted during Met Gala week, to pared-back separates that echo her signature quiet-luxury aesthetic.

A Shift in Tone: Minimal Styling During a Moment of Reflection

Just days before the Miami wedding weekend, the tragedy at the Astroworld Festival in Houston—headlined by Travis Scott—resulted in a mass casualty incident that claimed ten lives.

During this time, Kendall’s public presence shifted from the runway to social advocacy. Both she and Kim Kardashian used their platforms to express grief and solidarity with the victims, a stark contrast to the high-glamour appearances usually associated with their brands.

While Jenner’s 2021 Miami looks leaned into minimalist luxury, her ability to anchor a “visual statement” with specific footwear began years earlier.

To understand her current mastery of the high-low aesthetic, one must look back to her formative style moments in London, where she first began experimenting with the rugged-meets-refined combinations that would later become her signature.

Early Foundations: One Teaspoon Boots and Kendall Jenner’s London Style Era

Kendall Jenner steps out at night in a black-and-white fringed mini dress, carrying a structured leather bag as she keeps her look sleek and understated

During a visit to London in July 2015 to explore an Andy Warhol exhibit at Sotheby’s, she leaned into a bohemian-luxe aesthetic that felt worlds away from her 2021 looks in Miami.

Kendall Jenner steps out at night in a black-and-white fringed mini dress, finishing the look with sleek black ankle boots and a structured leather bag

She wore a striped, fringed dress from the Alice McCall Spring 2015 collection, accessorized with a B-Low belt and Saint Laurent sunglasses.

Most notably, she anchored the feminine fringe with rugged boots from One Teaspoon and a Givenchy tote.

Shielding herself from flashing cameras, Kendall keeps her off-duty style polished in dark sunglasses, a tasseled knit dress, and pointed-toe boots (Credit: Will Alexander / WENN)

This early look signaled her evolution into a fashion maven, influenced by her growing exposure to industry giants like Karl Lagerfeld and Olivier Rousteing.

A closer look highlights Kendall’s understated beauty styling, with aviator sunglasses and a monochrome palette anchoring the ensemble (Credit: Will Alexander / WENN)

One Teaspoon’s laid-back, rock-inflected aesthetic has also appeared on other style-savvy celebrities featured on Your Next Shoes, from Emma Roberts styling a One Teaspoon romper with Isabel Marant wedge sneakers to Gwen Stefani pairing a One Teaspoon denim skirt with statement knee-high boots.

The Australian label’s easygoing silhouettes have also been spotted in off-duty denim moments, like Alessandra Ambrosio’s relaxed One Teaspoon jeans styled with ankle boots, reinforcing the brand’s crossover appeal between casualwear and standout footwear.

The outfit’s sharp proportions come into focus as Kendall’s black suede ankle boots add edge to the short hemline

Kendall Jenner visits Sotheby’s auction house on Bond Street before heading off to see Lewis Hamilton at Claridge’s hotel in London on July 1, 2015 (Credit: Will Alexander / WENN)

Kendall takes in an Andy Warhol exhibition, her fringed black-and-white dress echoing the graphic repetition of the iconic artwork (Credit: Kendall Jenner’s Instagram)

Kendall Jenner’s Shoe Strategy, From Off-Duty Staples to Fashion Week Statements

From minimalist sandals and relaxed sneakers to polished loafers and Paris-ready boots, Kendall Jenner’s footwear choices consistently anchor her fashion moments. Explore more of her standout shoe looks and style evolutions below, curated by Your Next Shoes.