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    Home»Fashion»The Coolest Way to Wear a Dress and Loafers in Fall 2026
    Fashion

    The Coolest Way to Wear a Dress and Loafers in Fall 2026

    By AdminSeptember 30, 2026
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    Paris Fashion Week has kicked off in great fashion—not only on major runways (including Jonathan Anderson’s romantic Dior collection and Anthony Vaccarello’s rumored final Saint Laurent show) but also on the streets. Stylish dressers from around the world have descended on the city to showcase their finest street style, and Jennifer Lopez stands out as a clear highlight. No matter where she is, J.Lo always delivers effortlessly chic ensembles, and today, she showed the ultimate formula for styling a maxi dress this fall, pairing it with one of the season’s key flat-shoe styles.

    While taking a break from the shows to shop, J.Lo was photographed wearing an ivory lace slip dress, black loafers, and white socks. She completed the look with a Dior bag and aviator sunglasses.

    If I’m being honest, J.Lo’s outfit felt unexpected—and for good reason. First, she typically opts for platform heels or PVC pumps, so a fresh shoe style caught me off guard. Second, the contrast between the sophisticated dress and the casual flats and socks stood out. The juxtaposition is what made the ensemble look fresh, cool, and aspirational. It was a prime example of Allison Bornstein’s wrong-shoe theory.

    Latest Videos FromWho What Wear

    If you’re inspired to re-create J.Lo’s look, keep scrolling. Ahead, I’ve rounded up the chicest maxi dresses and loafers to wear this fall.

    The Dress-and-Loafer Outfit on J.Lo

    Jennifer Lopez wears an ivory lace slip dress with socks and loafers.

    (Image credit: Backgrid)

    On Jennifer Lopez: Khaite dress; Dior bag

    Shop Maxi Dresses and Loafers

    Z Supply Charisma Midi Dress

    Z Supply

    Charisma Midi Dress

    Every It girl’s fall wardrobe includes at least one simple black maxi dress.

    Lennon Loafer

    These new Nordstrom loafers, which also come in chocolate brown, look so expensive.

    Reformation, Cecilia Linen Dress

    Reformation

    Cecilia Linen Dress

    Just because it’s linen doesn’t mean you can’t wear it in the fall. Add loafers and a sweater around your neck, and you’ve got a chic autumnal look.

    ZARA, Suede Gathered Loafers

    ZARA

    Suede Gathered Loafers

    Satin Midi Dress

    Massimo Dutti

    Satin Midi Dress

    If I didn’t already own a similar style, I would buy this dress. I tried it on in the Madrid store and loved the way it fit.

    The Grayson Penny Loafer

    Madewell

    The Grayson Penny Loafer

    Carey Knit Halter Maxi Dress - Burgundy

    LE BOP

    Carey Knit Halter Maxi Dress

    Shopbop’s label Le Bop makes great elevated basics.

    Terry Patent-Leather Penny Loafers

    AEYDE

    Terry Patent-Leather Penny Loafers

    Burgundy loafers are just as versatile as black ones.

    Ten, Champagne Satin Dress

    Aritzia

    Champagne Satin Dress

    Yes, you can style this dress with heels, but I think it would look cooler with more casual shoes like loafers.

    Libby Loafers - Chocolate Crinkle

    Tony Bianco

    Libby Loafers

    Slip Cami Dress - Black

    The crinkled fabric adds just the right amount of dimension and polish.

    Bryant Leather Loafer

    Stuart Weitzman

    Bryant Leather Loafer

    I guarantee that these are worth the investment.