Taylor Swift, Katie Holmes and More Show How to Rethink Loafers, Oxfords and Derby Shoes for Fall

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Loafers, Oxfords and Derby shoes are not exactly newcomers when it comes to fall footwear. All three silhouettes have long been reliable work shoes, particularly once sandals start looking optimistic and boots still feel premature

Celebrity looks from recent fall seasons, however, have made the category much less uniform, with classic loafers and Oxford shoes turning up in faux-python, tortoise patent, burgundy leather and more unexpected styling

First, the basic difference, for those curious: a loafer is a laceless slip-on, while an Oxford is a lace-up traditionally defined by its closed lacing system. A Derby shoe, on the other hand, has an open lacing system — and some styles that are listed as Oxford shoes are technically Derbies, if you look close enough. Technical semantics aside, each footwear style can still do the obvious office work with trousers, tailoring and midi skirts — but that is only one way to wear them

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In November 2023, Taylor Swift wore Sézane’s Jessie with gray wide-leg trousers and an orange-and-tan Gucci argyle sweater for dinner in New York

The brown faux-python shoes featured a chunky heel and platform, picking up the warm tones of the sweater. The trousers were wide but short enough to leave much of the loafers visible, including the thicker sole

Katie Holmes brought out another fall combination in September 2025. She wore Franco Sarto’s Senna lug-sole loafers in tortoise patent with black socks, a black satin midi skirt and a camel knit sweater

The brown mottled finish worked easily against the neutral clothes, while the lug sole put some heft underneath the fluid skirt. It is a useful middle ground for that stretch of fall when bare legs still make sense but boots feel like overkill

Rosé’s September 2025 look made the case for pairing bright white socks with all black everything, including her black lace-up dress shoes

The shoes were technically Derbies rather than : the eyelet tabs sit on top of the vamp in an open-lace construction. The two silhouette names are often thrown around interchangeably, but Rosé’s look still showed that not all dress shoes have to accompany a dressy or office-ready outfit

Mindy Kaling skipped the usual black Oxford or Derby shoe in September 2025. Her Gianvito Rossi pair, the Vicky Oxford pump, came in burgundy, worn with a cropped Khaite cardigan, matching miniskirt and tights in the same wine-colored family

Instead of using the shoes to break up the monochrome look, Mindy Kaling carried the color all the way down. Burgundy is hardly difficult to bring into an office wardrobe either; it plays well with gray, navy, camel and black

The Colt has a high vamp, low-stacked heel and rounded, snipped toe, covering considerably more of the foot than a standard penny loafer

None of this requires retiring the loafers already sitting under a desk. The familiar black or brown pair still works with trousers on Monday morning. Fall’s more interesting options simply leave room for tortoise patent, burgundy leather, a heavier sole or a sock that does more than prevent blisters

Taylor Swift, Natalie Portman and More Celebrities Embracing the Loafer Shoe Trend [Photos]

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