What We Plan to Wear for Thanksgiving This Year + Our Traditions

Thanksgiving is a tough holiday to dress for because you want to be both comfortable AND cute. And sometimes it can be difficult to find a Thanksgiving outfit that checks both of those boxes.

Some family get-togethers may be fancy, and others may be much more laid-back. So we’re going to share what we’re planning to wear based on our Thanksgiving dinner plans (spoiler alert…neither of us are dressing very fancy for turkey day this year!).

Bridget’s Thanksgiving EnsembleBridget's Thanksgiving maternity wear

Let me first start by saying this Thanksgiving I am grateful for whoever invented the blanket sweater and over-the-belly maternity leggings- genius! Haha all jokes aside, this may be the comfiest Thanksgiving outfit I’ve ever worn. Finding maternity outfits that don’t feel super outdated (read: ugly) has been a lot harder than I anticipated. I’m happy that this option seems “put together”, not super maternity-ish, while also leaving lots of extra space for the growing bump and an XL Thanksgiving dinner.
Comfy maternity clothes can also be cute

I’ve purchased a few Target maternity tees and have been pairing these super comfy tops with jeans and in this case, black leggings. The blanket sweater is a little outside my comfort zone but it was too cozy not to try and so far I’ve really loved it.

It’s one size fits all, which made me a bit nervous at first. But I like that it doesn’t feel “overwhelming” on my body. And I also love that there are sleeves so it’s not constantly falling off me.

This casual, easy maternity wear is also super cute and comfy for ThanksgivingI haven’t had any luck finding black maternity pants that I love, so I’ve been wearing my regular black pants with a belly band to work. But since I want to be extra comfy this Thanksgiving, I opted for these black (over-the-belly) leggings that are SO soft. And you guys know how much we love our TOMS so it was a no-brainer to top off this comfortable yet “pulled together” look with our go-to fall/winter shoes.

Thanksgiving is actually one of my favorite holidays of the year! I love that the whole day is about being together, eating traditional food, and taking time to relax before the holiday craziness starts. Plus I love traditions and Thanksgiving oozes with them, which makes me extra grateful.

Bridget family photoMatt and I both have BIG extended families that get together for every holiday.  For Christmas, we travel to all of the different family parties, but for Thanksgiving, we split the day into the morning and afternoon and rotate which family we eat dinner with each year. This year we will do breakfast with his family and then head to my aunt’s for a large family dinner with my entire mom’s side.

Honestly, I don’t care where we end up each year, I’m just so thankful to spend time with our families. I also LOVE sipping coffee (decaf this year!) while watching the Macy’s Day parade. It’s been a tradition in our house forever and it’s definitely one I want to continue with our growing family!

Casey’s Thanksgiving EnsembleCasey's Thanksgiving outfit

Our Thanksgiving is SUPER laid-back and it only includes our immediate family. Even though we have a small group (less than 10 of us), it’s so nice for it to just be the core group of family. Less small talk with distant relatives, and more together time. Yes, please!Casey's Thanksgiving decor

Last year we actually hosted Thanksgiving at our place for the first time ever…which was amazing! But for most of my life, we’ve had Thanksgiving at my mom’s house in the suburbs. She recently moved to a gorgeous new place in the city (pictures coming soon) and is still getting settled.  So we figured we should have Thanksgiving elsewhere.

Now that everyone lives in the city (between my mom, us, my brother, and my sister we all live within a 2 miles radius!), it makes sense to have it at one of our places. My brother Harry and his wife Jackie just moved to a gorgeous new house in Bridgeport, so we will be having our turkey dinner there. They have a newborn baby girl, as well as my two-year-old godson, so we will all be bringing food to make it a tad easier on them!

Usually, we all get together around noon and have some drinks and appetizers. Then we’ll eat dinner around 4 or 5 pm. After we’re stuffed from the food, we play board games and hang out all together. In year’s past, we have a sleepover at my mom’s and the festivities last well into the night. Casey's family photo

In terms of wardrobe, things are really casual for our Thanksgiving holiday. However, we usually take our family Christmas card photo (the pic above is from last year) so no one wants to be too casual for the photo op. I think my outfit this year is the right mix between pulled together and comfortable.Casey's comfy and casual Thanksgiving outfit

This year I’m planning to wear leather leggings, a cozy oversized sweater, and my new leopard loafers.Comfy leather leggings

I’m obsessed with these leather leggings from Athleta (which they sadly no longer sell). They’re high-waisted so they suck it all in (even after a big Thanksgiving dinner!), and they’re stretchy and flexible. This will really come in handy on Thanksgiving day since I’m sure I’ll be running around after my nephew. The leather detailing on the front makes them a tad dressier than a normal black legging and I love that! These leather leggings from Spanx have amazing reviews, so if you’re looking to buy some leather leggings…I’d go with these! Plus that moto detailing is perfection. These BP ones are a great price if you want to try out this trend, without committing to a big purchase.

The sweater is a new purchase for only $45! I love the v-neck and the chunky knit on this top. It’s a little longer which is perfect to cover the booty. It’s loose in the mid-section, yet not too oversized to make me look larger. All in all, a great purchase! They have a few colors in this sweater, so there are lots of gorgeous options to choose from.These leopard loafers are amazing

Finally, these loafers. I was a bit hesitant to buy these because I have trouble with flats giving me blisters or being too flat for my feet. I’m so happy to say that these are incredibly comfy and it feels like I’m wearing slippers! There was no breaking in period and I’ve gotten zero blisters from them!

I truly think leopard is a neutral and can pair with just about any outfit. I’ve had leopard flats in the past and have wanted some new ones for quite some time. I’m really happy I scooped these babies up. I’ve been wearing them to work a lot because they make even jeans and a button-down look that much more pulled together.These flats are comfy and versatile

If you’re on the hunt for some new flats, I highly recommend these.

Casey's complete Thanksgiving ensembleOverall, I’m excited to wear this outfit to our Thanksgiving day celebration. Comfy, cute, with a bit of an edge. That’s a combo I can get behind.

If we were a fancy holiday family, I’d probably go with this dress, some tights, these boots, and this fun necklace!

Casey's Thanksgiving tableWith Thanksgiving a little over a week away, it’s time to start prepping for this holiday! What are you planning to wear to your Thanksgiving celebration? Do you get dressed up? Or is your family much more laid-back? We’d love to hear more about your Thanksgiving traditions.



The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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