14 Easy and Effortless Winter Dresses That Are Affordable Too

I've never really considered myself much of a dress person, but when it comes to those days when I just can't seem to put together an outfit , a dress is a one-stop garment that just makes the process much easier. While the clothing style may be considered an item solely for spring and summer, there's nothing I love more than throwing on a dress in the colder months with a thick pair of stockings and boots. Not only does it take less than 10 minutes together, but it looks good, too.

Thanks to our namesake clothing line, we've got you covered with a variety of dresses suited for the winter months that are trendy and affordable. Think muted colors, velvets, and comfy knits. Scroll below to see the under $50 winter dresses we'll be stocking up on, plus some outfit inspiration along the way. 

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(Image credit: @sarahkretzu)

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(Image credit: @shhtephs)

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(Image credit: @thedailynsreen)

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(Image credit: @wendymakss)

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(Image credit: @whowhatwearcollection)

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Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.