What to wear for Thanksgiving

For those of us who aren't getting too dressed up (and also avoiding hard pants!)

This past week was a whirlwind. On Tuesday, I spent a good part of my morning trying to figure out where I could take the baby to get the RSV vaccine after it became clear that our pediatrician’s office would not get doses. I finally got an appointment for her, only to end up in the ED that evening to get her breathing checked, resulting in a confirmed RSV diagnosis. Thankfully she is fine. Lots of sleep, nose suction, and sitting in the bathroom with a hot shower running did wonders and she is well on her way to feeling like herself again. And my older kids are fine as well.

But man, sickness in your kids is so painful to see and so hard to deal with. For the one-millionth time, I was so grateful for our wonderful nanny who helps to make sure everything runs smoothly and continues to provide care for my kids even when one (or more!) of them are sick. It meant I didn’t need to take any time off from work, which would be tricky when I have only been back for a week, and it meant that we have extra help with the kids at home that I love and trust. To anyone who is dealing with or worried about sickness this season, I’m sending you a huge hug!

And somehow, we find ourselves just a few days away from Thanksgiving. It’s just about as early as it can be this year, and not only has it come up on me so quickly, but I also feel like we are losing a whole week of the year because the last week of November is just getting skipped over. Christmas things are starting earlier, people will mentally be in December for the whole last week of November. I truly can’t believe that we are at the end of the year. I need a better system in place to keep track of all the holiday stuff that I am responsible for planning!

But, one holiday at a time. This may be an unpopular opinion, but I’ll say it anyway. Although I love Thanksgiving, Thanksgiving with little kids, kind of…sucks.

Yes, (complicated history of the holiday aside) Thanksgiving is a wonderful opportunity to teach your children about the importance of gratitude, to see family, and to gather together and reflect on all the things you are grateful for, and that is important and amazing. However, a day that revolves primarily around spending a lot of time preparing a large meal and then sitting down to and leisurely enjoying said large meal - well that is something that little kids (or at least my little kids) do not give a f&ck about.

I have a lot of nostalgia for a Thanksgiving spent making many intricate dishes, watching the Macy’s Day Parade, and then transitioning to football games, with some favorite Friends Thanksgiving episodes sprinkled in. Having a large meal, many glasses of wine, taking a little nap, enjoying a course of desserts and playing various card or board games for hours.

We will be lucky if we get a few minutes of everyone sitting at the table together. Actually, I have no idea if that’s even a realistic picture for me to have in my mind! My kids might not even eat any part of the meal. My son told me he’s most excited to eat ice cream - you know, that classic Thanksgiving dish!

But of course, we will still gather! We are staying local this year and so we are planning to participate in the Turkey Trot that our town hosts every year. We may try to check out the football game at our local high school! If the weather is good I’m sure we’ll also spend lots of quality time at the playground, or maybe go for a bike ride! And, we will sit down to a meal with family. Thankfully, mostly prepared by my Dad & sister (or at least, I hope; we have aligned on a menu but not on actual cooking duties, so we shall see about that!)

And so, of course, there is the consideration of what to wear. While I love to get dressed up, and will always take advantage of an opportunity to be just a little overdressed, I am also extremely focused on function when I dress for Thanksgiving. I want to be able to sit on the floor with my kids, follow them around my parent’s house whilst making sure they don’t touch anything they aren’t supposed to (everyone’s favorite holiday sport, amiright?), and eat a gigantic meal + many snacks without feeling uncomfortable!

Also, I rarely ever buy anything new for Thanksgiving. It’s a pretty casual holiday for us, and mostly limited to a celebration with immediate family, even on the years when we have traveled to celebrate with my in-laws. So, it’s all about shopping my closet (which hopefully you know by now that I am a huge proponent of), and finding a combination that feels special, a teensy bit festive, and of course, comfortable!

So four things that I am considering wearing and the recipe/formula that you could follow if you want to recreate it with pieces you already have - because, just as a reminder, you probably don’t need more stuff (although you might need more ideas!) - and you certainly don’t need more stuff JUST to wear for Thanksgiving!

RECIPE NUMBER 1: SLIP SKIRT + SWEATER + FLAT (OR KITTEN HEEL)

Sweater (Similar) / Maxi Slip Skirt / Flat Slingbacks

This is a go-to winter outfit for me. I finally, finally, found a great maxi slip skirt (I have ordered and returned about 10 I think!) and I am extremely sorry to say that it is now backordered until the end of January. If you can wait until then though, it’s really great. I think it runs pretty big, I took a 6 and probably could have sized down, but I like the slightly loose fit. Also, not me telling you I just bought something new after I just wrote multiple paragraphs about NOT needing to buy anything new - but, to be clear, I didn’t buy it specifically for Thanksgiving - a skirt like this was on my seasonal wish list. If you’re looking for a maxi skirt that doesn’t break the bank - this one comes highly recommended (Anthropologie, $99), as does this one (J.Crew, $98) I have it in the midi-length!) A couple more ideas here (Favorite Daughter, $198), here (Anine Bing, $400) and here (Reformation, $218). If you don’t have a slip skirt, you can wear a slip dress (Madewell; $98, but also 40% off right now)! A little tip for getting a good tuck on your sweater - you can tuck the bottom of your sweater into your bra, to get a nice, even tuck, without bulkiness, but I often find that my sweaters are too short for that (even longer ones!) Another tip is to wear a skinny belt around your waist, under your sweater, and then you can tuck your sweater into that! As far as shoes, I am wear a go-to neutral flat in this outfit; any flat will do. You could also do a tall boot (Banana Republic, $450), or a kitten heel boot (Staud, $395), whatever you love the most!

RECIPE NUMBER 2: SWEATER DRESS + PENDANT NECKLACE + CLOG (OR BOOT)

Sweater Dress (old, similar), Loeffler Randall Clogs

This one is so so so simple. Any sweater dress will do, with your shoe of choice. My dress is from H&M last year, this is similar. Some other sweater dresses I love: This black one from Dissh is on my wishlist ($160), this from Mango ($60, included in Black Friday Sale), and this one (Sezane $218). If you like a mini, this is so cute (Madewell, $138).

I like the slight height that a clog gives me, but I wear this dress with tall boots, chunky moto-boots, ballet flats, loafers, you name it. Add a layer with a blazer on top. Wear a belt if you want a little shape. Add some additional interest with an even larger or longer pendant necklace, or a scarf around your neck. Sweater dresses are also my winter uniform when I’m pregnant. I will say, not the most convenient if you are nursing/pumping, but I will wear when I know I will be able to nurse somewhere totally private and just lift the dress up!

RECIPE NUMBER 3: WIDE-LEG PANTS + WRAP CARDIGAN (OR BELTED SWEATER)

Belted Sweater (old, similar) / Pants (old, similar), Flats

This is probably what I will be wearing this Thanksgiving! A high-waisted, stretchy waistband pair of satin pants - perfect to eat a large meal in and feel like you’re wearing sweats but not. You could wear knit pants (COS, $135), or even your favorite pair of high-waited trousers (Reformation, $178). Add in my favorite wrap sweater, and simple flats (I’ll swap in a boot if its extra cold!) This is also a great maternity outfit - I wore this sweater throughout multiple pregnancies because you can tie it above the bump, and wear it open! It’s especially great if you get dressed up for work! My sweater is from MM LaFleur, which is a fabulous woman-owned brand that makes work and travel-friendly clothing. It looks like it is no longer available, this (MM LaFleur, $185) is very similar, and I love it!, and this is also similar, but more of a blazer situation (MmLaFleur, $325). This has a similar look at a lower price point (Gap, $128), as does this (MaxMara $198)! Any cardigan would work great here, if you have a longer one, you could belt it with your own belt!

RECIPE NUMBER 4: WIDE-LEG JEANS + SWEATER + FUN BALLET FLAT (AKA, THE LAST RESORT if you must wear hard pants)

Sweater / Jeans / Flats (old, similar)

Can you tell that jeans aren’t my first choice for Thanksgiving? Too constricting. I want to eat as much as I want in peace. Form and function, always, and the function I need on this holiday is not feeling like my waistband is too tight at any point in time. That said, if you really want to wear hard pants, I would recommend a pair of jeans with at least a little stretch. My favorite pair right now are these Levis (Levis, $98). They are just a really great jean - a true denim with a tiny bit of stretch that helps the jeans fit so well! I also really like the pair pictured - they are a much stretcher denim, but I love the crop, the slightly kick flare, they are super flattering. This pair is very similar at a lower price point (Gap, $70). Pair with your favorite sweater - either tucked or untucked, whatever your preference is. Add a bit of fun with your shoe choice - I love a silver flat (Margaux, $198) because it feels festive but I also wear these flats for everyday. If you have a red or blue flat that would be fun too, or even a little kitten heel!

I hope you have a wonderful, relaxing and peaceful holiday. I am so grateful that you are read and reading!

Thank you for reading!

Thank you for taking the time to read this post, I am so glad you are here. I hope you enjoy reading it as much as I enjoy creating it. If you like what you’re reading, please consider:

📱 Screenshotting your favorite part of this newsletter and share it on Instagram. Be sure to tag @ct_shopguide and I’d love for you to follow!

💌 Forwarding this email to a friend

👩‍💻 Commenting and liking this post on Substack!

All products highlighted are chosen by me, and some may be affiliate links. Your support is appreciated!