What to Wear for the Holidays? Think Fabulous Dresses and Sensible Bags 

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Photographed by Phil Oh

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If fall is the season of minimalist slip dresses and impractical yet beautiful evening pouches, this holiday season is poised to flip that dynamic—in other words, statement-making dresses paired with smart bags. Seen on and off the runways this Fashion Week, from Valentino’s spring 2020 runway show to street style stars from all four cities, this trend is easy to make your own in time for the holidays. How to put together this effortless look? Instead of reaching for a typical sequin dress, opt for something more voluminous and fantastical. As far as an evening bag goes, switch out those fancy mini bags and fragile acrylic clutches for a functional day bag. A tote, a structured crossbody, or a shoulder bag is large enough to carry your iPhone—and a bottle of wine for your Thanksgiving hosts.

A blue Valentino Garavani VSling Shoulder bag will add a pop of color to any winter wardrobe, dressing up any neutral-colored party dress. Paravel’s canvas tote and Tamara Mellon’s versatile crossbody bag make a perfect day bag as well as evening when styled with a fanciful frock. Below, eight dress and bag pairings to shop now before your weekends fill up with holiday gatherings.

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Photographed by Phil Oh
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Cecilie Bahnsen Cotton Macy Ribbon Tie Dress

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Valentino Garavani Small VSLING Shiny Calfskin Shoulder Bag

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Leal Daccarett Idilio Ruffled Silk-Faille Dress

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Gabriel for Sach Leo XL Brown

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Photographed by Phil Oh
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Cult Gaia Shannon Feather-Embellished Silk-Tulle Mini Dress

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DeMellier London The Vancouver

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HVN Paula V-neck Sequined Dress

Chylak Croc-Effect Leather Shoulder Bag

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Photographed by Phil Oh
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Stine Goya Jasmine Jacquard Mini Dress

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Tamara Mellon Kiss Bag

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Molly Goddard Bronwyn Tulle Midi-Dress

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A.P.C. Maelys Leather Cross-Body Bag

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Photographed by Phil Oh
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Merlette Soliman Tiered Minidress

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Paravel Pacific Tote

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Simone Rocha Dawn Off-The-Shoulder Taffeta Dress

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Kate Spade New York Medium Toujours Leather Crossbody Bag