My Favorite Dresses for This Winter (and Beyond)

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My Favorite Dresses for This Winter (and Beyond) | Wit & Delight

Thinking about putting your favorite dresses into storage for the winter season? You might want to consider keeping them around.

When it comes to getting dressed in the morning for a day of staying (mostly) at home, I’ve found that there are few style approaches more simple than throwing on a dress. And while dresses may be slightly more synonymous with summer than winter, there are ways you can seamlessly transition these wardrobe staples from season to season.

Below, I’m sharing my tips for doing just that, no matter how far north you might reside. Here’s to simplifying the process of getting dressed well into the winter months ahead. After all, we’re mostly just dressing for ourselves this winter…why not have a little fun with it?

1. Warm-Weather Dress, Styled for Winter

My Favorite Dresses for This Winter (And Beyond) | Wit & Delight

Flowy summer dresses might not seem like a suitable option for the dead of winter, but wearing them is one of my favorite ways to shake up the winter wardrobe fatigue that comes from wearing sweaters day in and day out. A thin bodysuit looks great under silk cami dresses, and a chunky sweater worn atop sweet summery prints gives the seasonal look a refresh.

The dress below was given to me as a birthday gift, and while it’s definitely above my standard price range, I consider it an investment piece that I’ll wear for many, many years to come. And I love that the purchase supports not one but two women-owned small businesses (Idun and La Reunion Studio).

Product Sources: Above: Silk Eva Slip Dress, $148 (currently on sale for $99) from Madewell | Below: La Reunion Studio Patchwork Dress, $435 from Idun

2. Knit Dress

Here we have the quintessential winter frock: the knit dress. I’ve lived in one black turtleneck tunic since the winter I was pregnant with August almost five years ago. It’s a style that will always be classic and, as an added bonus, it’s super comfortable and flattering. 

Product Sources: Above: Belted Rib Midi Dress, $129 from & Other Stories | Below: Rib-knit Dress, $34.99 from H&M

3. Nap Dress (à la Pride and Prejudice)

This was my look du jour all summer long. I love the idea of wearing a long black turtleneck under my puffy-sleeved dresses to help transition them into the winter months. Pair your nap dress of choice with Blundstones, chunky socks with tights, and a beanie.

Product Sources: Above: Oversized Ruffled Maxi Dress, $99 from & Other Stories | Below: Jasmine Dress, $188 from Mille

4. Structural Dress 

Prefer a less flowy dress? You can do the same tights/boots/beanie combo with a more structural frock. 

Product Sources: Above: Esther Mini Dress, $148 from Anthropologie | Below: Textured Button Up Hourglass Mini Dress, $89 from & Other Stories

5. Classic, Colorful Shirt Dress

Are you someone who tends to be committed to neutrals? Infusing a little color in a classic shirt dress might be just what your closet (and mood) needs this winter. Color block with fun socks, tights, or a knit cap.

Product Sources: Above: Bea Dress Blue, £100 from Kai Collective | Below: Mini Shirt Dress, $89 from & Other Stories

What dress styles will you be wearing all winter long?

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