How to Holiday

Stylish, Stretchy Thanksgiving Outfits That Leave Plenty of Room for Dessert

Go ahead, have that second piece of pie.

Even if you’ve never literally popped a button from overindulging, on at least one day a year, it's not an unreasonable fear. We're talking, of course, about Thanksgiving.

The food-centric holiday doesn't exactly play well with body-con dresses, slender silhouettes, or anything else that could be described as fitted. What you want to feast in is an outfit that lets you eat with impunity.

With that in mind, we hunted down Thanksgiving looks that are as forgiving as they are flattering. 

Eliza J Fit & Flare Sweater Dress

I know, I know, you’re thinking, "That’s your idea of a forgiving dress?" But take a closer look. Yes, it’s fitted from the sleeves through the bodice, but see how it then flares out just below your ribcage? No one will ever see that little pouch expanding with turkey and stuffing and cranberries and four or five Pillsbury Crescent Rolls.


Vince Cashmere Tunic

Or why not just go into full-on sweatsuit mode — but in a way that even your kind of judgy grandma won’t raise her eyebrows over. Start off with this cashmere sweater, which shares a sweatshirt’s basic silhouette, but with a cut-out shoulder detail that keeps it interesting. And then...


Everlane Cashmere Sweatpants’ll want to pair your cashmere sweatshirt with — what else? — cashmere sweatpants, an item that might be the single best idea ever.


Leith Blouson Sleeve Cardigan

You already know that your Aunt Jane has a philosophical objection to setting the thermostat above 68, so come prepared. Not only is this cardigan warm and cozy, its complete lack of a nipped-in waist means you can stuff yourself with impunity.


NYDJ Marilyn Jeans

Balance your oversized cardigan with a pair of skinny jeans by NYDJ, which were made precisely for occasions like this. Using some sort of sartorial magic, the brand’s pants manage to squeeze in your belly in while also being stretchy enough to accommodate all that pumpkin pie you just can’t stop eating. 


Robert Rodriguez Tie-Front Blouse

This perfectly tailored blouse appears as proper as can be for a holiday feast, but its sneaky tie at the front disguises all kinds of gluttonous indulgences.


Raquel Allegra Relaxed Pants

Pair your tailored blouse with elastic-waistband pants, which studies prove significantly lower your chances of feeling post-dinner shame.


Vince Deep V-Neck Sweater

How does such a roomy design still manage to look so sleek? We’re not sure, but all we really need to know is that the A-line cut leaves plenty of room for dessert.


Splendid Paperbag Skirt

This leatherette skirt’s accommodating waist is as is stretchy as can be, but the loose design is cleverly balanced by a short length that’ll keep the focus on your legs.


Topshop Tie Front Minidress

Slip on this sleek dress and tie the front. Loosen throughout the day, as needed.

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