I’m convinced no one does off-duty model style like Kendall Jenner. The second-youngest Kar-Jenner’s outfit formulas are never complex or overdone and yet she always looks effortlessly put-together.
Having worked in and written about fashion for many years now, I’ve spent some time cataloguing Jenner’s looks and can say with some certainty the model continues to favour the same pieces.
There’s her impressive collection of caps and her penchant for a straight-leg jean, but it’s her shoe choice that’s inspired me most, regularly spotted in a casual loafer.
Rather than the it-sneaker of the season or a sultry heel, the model is, more often than not, seen sporting a classic black penny style.
The shoe pairs effortlessly with jeans, pants and skirts as well as stockings or socks, making for the perfect alternative when your winter boots grow tiresome.
As demonstrated by Jenner, the shoe’s appeal stretches far beyond the cold season too — the loafer works just as well with shorts come summer. For shorter hemlines, Jenner opts for loafers alone – sans socks – to elongate her legs. When it comes to pants and mid-length silhouettes, either option works well.
Find all the styling inspirations you seek, plus our favourite loafers of the season, below.
RELATED: The Loafers Every Fashion Lover Needs In Their Forever Wardrobe
How To Wear Loafers, Inspired By Kendall
Layered Under A Coat And Skirt
Between Paris Fashion Week fittings, Jenner proved loafers are just as much a jet-set staple, wearing the understated pair with white socks, layered beneath a grey wool coat, white tee and calf-length skirt.
With Short Shorts Or Mini Skirts
Jenner is known to rock a no-pants look on occasion, but some of our favourites have been grounded with a pair of loafers.
Whether it’s stepping out for lunch in a pinstriped shirt and, per some angles, little else underneath or an oversized blazer and sports cap, she proves a mini is primed for loafer-pairing.
With A Turtleneck And Midi Skirt
During Milan Fashion Week, Jenner channelled 90s minimalism in head-to-toe black: a rolled turtleneck, a midi skirt, oval sunglasses and heeled loafers — proof the shoe scales up as easily as it scales down.
With Jeans And A Jumper
When Jenner and best friend Hailey Bieber turned up to a bowling outing in matching The Row Canal Loafers, it was proof the formula barely needs adjusting to work off-duty.
Wide-leg jeans, a red knit and crisp white socks peeking out kept the otherwise polished shoe a little more low-key.
Our Favourite Loafers For 2026
EOS FOOTWEAR
Ganten Loafer
TONY BIANCO
Libby Loafer
THE ROW
Ruched Almond-Toe Loafers
GUCCI
Loafer With Horsebit
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