Kendall Jenner Is So ’90s With Boyfriend Devin Booker in Tank Top, Jeans & Driving Loafers

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Kendall Jenner brought a dressy spin to off-duty travel style while in Los Angeles today with her boyfriend, basketball player Devin Booker.

Arriving from big sister Kourtney Kardashian and Travis Barker’s viral wedding in Italy on Tuesday, the FWRD campaign star strolled down the street in a pair of blue jeans. Paired with the casual bottoms was a light gray tank top with a rounded neckline and layered trim. Complete with an updo, dark oval-shaped sunglasses and delicate silver drop earrings, Jenner instantly channeled the off-duty ’90 style similar to looks of the era worn by stars including Drew Barrymore, Victoria Beckham and Gwyneth Paltrow.

Kendall Jenner, Devin Booker, jeans, blue jeans, tank top, gray top, sunglasses, tote bag, Los Angeles, loafers, driving loafers, black loafers, leather loafers

Kendall Jenner arrives to Los Angeles with Devin Booker on May 24, 2022.


Finishing her outfit was a versatile black leather tote bag.

When it came to shoes, rather than opt for warm weather go-tos like flip flops, thong sandals or slides, Jenner went the opposite direction and slipped into a pair of driving loafers. The black leather pair featured almond-shaped toes topped with short tassels, as well as top-stitching that pulled the leather inward for a further vintage effect. Faint flat heels, similar to many menswear styles of the same type of shoe, completed the pair. When added to her casual outfit, Jenner’s loafers appeared even more vintage-inspired and added a contemporary finish to her look.

Kendall Jenner, Devin Booker, jeans, blue jeans, tank top, gray top, sunglasses, tote bag, Los Angeles, loafers, driving loafers, black loafers, leather loafers

A closer look at Jenner’s loafers.


Booker looked equally ’90s, complementing Jenner’s outfit in a gray crewneck sweatshirt and black trousers, paired with sunglasses and pale gray Converse sneakers.

The occasion comes after several shoe-related moments for Jenner going viral in recent months. Earlier this spring, the model gained a wave of online reactions for threatening to block comments about her toes on Instagram for photos snapped while wearing platform thong sandals. Most recently, while at Kourtney’s wedding weekend, she was filmed by sister Kylie on Instagram while struggling to move up a set of stairs in a particularly slim-fitting silk Dolce and Gabbana gown; in an attempt to make the uphill hike easier, she wore a pair of Birkenstock’s beige suede Boston clogs.

For footwear, the former “Keeping Up with the Kardashians” star typically wears a variety of both classic and trendy styles. For events and formal appearances, Jenner regularly dons strappy sandals and mules from brands like Amina Muaddi, Bottega Veneta and Saint Laurent. For off-duty moments and casual ensembles, she can be spotted in Nike and Converse sneakers, Birkenstock sandals and a range of boots from brands like Khaite, The Row and Stella McCartney.

Sharpen up your style in loafers.

Sam Edelman Dandrea Slip On Tassel Loafer Flats

To Buy: Sam Edelman Dandrea Slip On Tassel Loafer Flats, $105 (was $140). 

Dr. Martens Bethan Platform Casual Shoe

To Buy: Dr. Martens Bethan Platform Casual Shoe, $150

Steve Madden Brenton Patent Leather Shoes

To Buy: Steve Madden Brenton Patent Leather Shoes, $60 (was $80).

Discover Jenner’s starring role in FWRD’s Summer 2022 campaign in the gallery.

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