34 Thanksgiving Dresses That Are Cozy, Cute, and Comfortable Enough to Wear for Second Servings
Thanksgiving always proves to be one of the trickier events to dress for. While I want to look presentable and stylish, I also want to feel unrestricted and comfortable in my ensemble because, well, mashed potatoes. In an effort to look put-together while avoiding restraining pieces, I'm opting for breezy fall dresses in multiple hues and fits this year. Not only is it a less restrictive option, but a dress is also an instant outfit. It'll help you avoid the struggle of pairing pants, a sweater, and a blouse moments before running out the door or getting up to help yourself to a second serving of your family's favorite dish.
Whether you're heading home for the holidays, attending a Friendsgiving, or meeting your significant other's family for the first time, opt for a stylish dress that feels appropriate, on-trend, and, most importantly, comfortable. Not sure where to start? Scroll to shop my favorites at every price point.
I own this dress in two other colors already and wore it to my family's festivities last year, so when I was searching for the best Thanksgiving dresses, I knew this silky yet breathable Réalisation dress would top the list.
Eloquii has been killing the game with its offerings this year.
Hill House Home's iconic Nap Dress just got a dressy upgrade with this comfy yet chic midi dress.
If you fell in love with Chloé's bohemian romance–inspired collection, this merlot dress should be your newest buy.
I have this dress in the V-neck version, and it's so comfortable. I've flown over five hours while wearing it.
I have this dress, and yep, it's just as good IRL as it looks online.
You can wear this chic dress on its own or pair it with mid-wash jeans, similar to the styling above.
This is my favorite comfortable fall dress when I want to look like I've put tons of effort into my outfit.
This chic dress is perfect if your family likes to have a dressier Thanksgiving.
This brand may be Australian, but it does Thanksgiving dresses so well.
Three of my friends have this dress, and I low-key might copy them.

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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