We'll Still Be Wearing This Fall Dress Trend in 5 Years—Shop My 25 Favorites

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(Image credit: Free People)

Right now, I'm transitioning everything in my wardrobe over for fall and winter. I've just swapped out my sandals for boots and pulled out my chunky knit sweaters from the back of my closet. And with all this closet reorganization comes another category: dresses. Yep, you guessed it. I've just put away my light sundresses until next spring and am replacing them with fall-ready long-sleeve midi dresses.

There are dress trends, and then there are dresses that are classic enough to be categorized as a fall staple. IMO, midi dresses with long sleeves fall into the latter category because the style is one that just never seems to quit. No matter what the dress trends du jour are, I'm confident that there will always be a spot in my closet for a few of these midi-length numbers.

Ready to dive into this roundup of fall dresses you can wear now and own for years to come? Scroll down to shop my favorites that I'm already envisioning with other seasonal staples like boots and jackets.

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(Image credit: @tamaramory)

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(Image credit: @lefevrediary)

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(Image credit: @eniswardrobe)

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(Image credit: @yasminedevonport_)

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(Image credit: @abimarvel)

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Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.