How to Holiday

Comfortable (But Cute!) Thanksgiving Outfits with Plenty of Stretch

Go ahead, have that second piece of pie. These stylish holiday outfits have plenty of room for dessert.

Even if you’ve literally never 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. You want an outfit that won't squeeze your waist — especially after you've helped yourself to a second (third?) slice of delicious pie. 

With that in mind, we hunted down Thanksgiving looks that are as forgiving as they are flattering. With plenty of stretch and give, you can guarantee you'll be comfortable from the appetizers all the way through dessert — without sacrificing style. 

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.


Halogen 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 high-low hemline detail that keeps it interesting.


Everlane Cashmere Sweatpants

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


Long 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 without fear.


NYDJ Marilyn Jeans

If you're thinking that jeans are the exact opposite of comfortable, hear us out: NYDJ is a jeans brand built entirely around ensuring they're the stretchiest, most comfortable jeans you'll ever find. Even Oprah has sung the brand's praises. Pair these with your oversized cardigan and you're good to go!


Tie-Front Button Cozy Top

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


Stretch Jeggings

Are they jeans? Nope, but that's your little secret. Pair your tailored blouse with elastic-waistband jeggings, which studies prove significantly lower your chances of feeling post-dinner shame.


Ribbed Turtleneck Tunic 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.


J.Crew Pull-On Velvet Skirt

This velvet 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.


Tie Front Mididress

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

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