Thanksgiving Day Outfit Inspiration for All the Ways to Celebrate

If you’re one of my American readers, how will you celebrate Thanksgiving this year? While most of us are aware of the traditions surrounding this annual holiday – Macy’s Thanksgiving Day Parade, a dinner complete with turkey, stuffing or dressing and potatoes, a turkey induced comatose state nap in the afternoon and maybe some football on the television while browsing the Black Friday Sale listings – families generally put unique spins on it. And since many of my readers, like myself, are over 50, I know that many of you may be doing things differently now than you did while raising your families. So in the spirit of Americana spiced with a bit of individualism, I’ve rounded up some Thanksgiving Day outfit inspiration for all the ways to celebrate one of our favorite days of the year.

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First as a pastor’s family living far from our relatives and now as empty nesters (still living far from most of our family), James and I are accustomed to spending Thanksgiving a little differently each year. We’ve celebrated in a cabin in the woods, outside a tent, gathered in friends’ backyards, around our own table with active military members far from home, at restaurants, hiking through the woods and seated around large tables with family. No one Thanksgiving has been just like the others, and we’re fine with that. The important thing is that we pause to express our gratitude to God for our blessings and that we break bread with someone we love…even if it’s just each other.

Depending on where we’ve been and what’s been on the agenda, I’ve dressed a little differently for each celebration, too. None of the outfits below were created specifically for this national day of thanks. But my hope is that we can use them for outfit inspiration – outfit starters, if you will. Take what you love and tweak the rest to suit your taste and your day of thanks, however you celebrate it.

The “Comfort Rules” Celebration

This year we’ll actually be celebrating Thanksgiving as well as my son’s birthday on the 27th. We’ll go over the river and through the woods to his home near Columbus, to spend a day or two with Daniel, his wife Stephanie and their dog Cooper.

We won’t have turkey since he’s not a fan, and that’s fine with me. This mama just wants to be with her kids and really doesn’t care what’s on the table. But Daniel will smoke some kind of tasty meat in his smoker overnight and Stephanie and I will create a few good dishes to accompany it. The day will be casual and slow, and comfort will rule, so I imagine I’ll wear something like the outfit above minus the boots. I’ll swap in my Brunch slippers instead.

If comfort rules your casual celebration of Thanksgiving, you may want to wear soft, cozy pants, too. The Ayr High Hopes pants above look a little more polished, but they’re super soft and comfortable. Top them with a t-shirt and sweater for an easy on the eyes combination.

Another comfy pant option is the Spanx AirEssential wide leg pants shown above. They come in lots of nice colors, including a brilliant red and a trending brown. Mine are black and they’re so versatile. I like to travel in them, but I especially enjoy wearing them around the house. These pants come in a full range of sizes and include petite and tall lengths. I wear them in a size large.

If you prefer something a little more street-worthy, but still want to be comfortable, you may like to celebrate the day in an outfit like the one above. These Lands’ End corduroy pants are super comfortable (I’m wearing them right now!), and when you top them with a simple t-shirt and flannel shirt you’ll feel pulled together but still casual.

Hosting the Casual Family Celebration

If you are hosting a family gathering for Thanksgiving, but your family keeps things pretty casual, you might enjoy looking a little more polished but still comfortable.

I selected these particular looks because they do include slipper type shoes, but not house slippers, so to speak. And because I started with the shoes, these looks also include jeans or pants that work nicely with flats. The pants above a super comfortable and modern, but they’re almost sold out. I wear a medium.

But you could also wear flats like my M.Gemi Una ballet flats with cropped length jeans, like the slim wide leg jeans shown above or the slightly slimmer jeans shown below. The above outfit is a simple sweater and jeans combo. Below I’m wearing a suede jacket, but you could leave that off for a stay-home look.

If you are hosting a casual family celebration, but plan to wear something a little dressier, you could wear a simple wide-leg jeans and half zip top combination like the one shown below.

The only problem is that most of my wide leg jeans require me to wear at least a little bit of a heel. So if that’s fine with you, go for it. The outfit above still looks casual, and you could swap in sneakers or clogs if you like.

The jeans and lightweight floral pink sweater combo above is similar. And below I’ve just got a good example of the most basic sweater and jeans combination. Still, it’s smart and polished, easy and effortless.

I think the key to dressing for a casual dinner that you’re hosting for multiple family members is to wear something that feels comfortable for the tasks at hand, looks a little polished and pulled together but also puts others at ease. This is not the time to put on airs, of course. This is family!

For over ten years while in Arizona, our family actually began each Thanksgiving by volunteering at the Salvation Army community meal. The outfits above are also perfect for volunteering. The tips below apply to such opportunities as well.

Keys to the Hosting Family Casual Thanksgiving Outfit:

• create an outfit that feels good but also looks a little special
• keep the fabrics soft and comfortable, but select items with a little polish
• accessorize simply, in a way that doesn’t interfere with the tasks of hosting
• start your outfit with your shoe choice, whether that’s flats or low heels

Invitation to Celebrate Casually

If you’re invited to a casual celebration at someone else’s home, things change a little. These days I think it’s smart to consider whether you’ll be expected to remove your shoes or not. At my son’s home we’re certainly not forced to remove our shoes, but it is their custom, so we gladly oblige. But that means I have to take along my slippers because my metatarsalgia prevents me from walking all day in my sock feet.

Likewise, if you know you’re going to remove your shoes in someone’s home, you’ll want to wear good socks or carry along some house shoes. (Remember, we’re talking about a casual gathering here.) The train of thought continues, however. If you’re going to remove your footwear or even change into slippers, you’ll want to wear pants that won’t drag the floor once you’ve done so. Hahaha! It’s a lot to consider, isn’t it?

On the other hand, if you don’t expect that you’ll be removing your shoes, you have the freedom to wear something casual but a little more elevated, like booties or kitten heels. Jeans and sweater outfits take on a more elevated feel when you wear nicer footwear.

Still you’ll want to choose jeans and a sweater that are casual enough for a day of varied activities, such as putting together a puzzle, helping out in the kitchen, playing a little with grandchildren, sitting outside on the deck if the weather allows, etc.

Another option is to wear a short sleeve sweater like the one above. If you are concerned about getting warm in a home filled with people and heated ovens, this might be a smart option. Simply add another layer for going to and from the event.

Finally, another option would be a button up shirt with a jacket. You might feel even more comfortable in this top. And you could swap in sneakers for any of these outfits if you feel the occasion calls for more casual footwear. Plus, you’d be ready for that annual walk around the block. Some call it the turkey trot!

Keys to the Invitation to Celebrate Casually Outfit:

• consider whether you’ll be removing your shoes indoors
• start your outfit with your footwear in mind
• accessorize your outfit and pull it together with styling techniques
• wear something that looks polished and purposefully put together, but also casual enough for possible activities
• consider the indoor temperatures as well as the outdoor weather

Celebrating at a Casual Restaurant

We’ve celebrated Thanksgiving a time or two at casual restaurants like Bob Evans and Cracker Barrel. One other year when the holiday fell on Daniel’s birthday and he was ill, the other three of us ended up at Golden Corral after volunteering at a community dinner at the Salvation Army. Not our finest meal, ha!

But honestly I kind of enjoyed the dinners at the other casual restaurants. Everyone was in good spirits and the clean up was…zip! So if that’s your plan for this Thanksgiving, ain’t no shame in that! Again, our celebrations are all different, but we can enjoy the day for what it is…an opportunity to express our gratitude to God for His blessings and break bread with someone dear. Truly, let’s be appreciative if we can check just those two boxes.

The key to getting dressed for a Thanksgiving dinner at a casual restaurant is to remember that it is what you make it. I encourage you to make it a true celebration by putting a little extra effort into your outfit. Wear something you enjoy wearing, something a little special that makes you feel pretty.

The outfit can still be simple and comfortable. But choose a festive, feminine blouse, like the ecru guipure lace button front shirt above instead of a sweatshirt or tee. Wear some pretty booties and favorite jeans. Top the look with a casual but on trend jacket.

It’s also smart to add a little color. The people working at the restaurant will enjoy seeing you show up in a cheerful red jacket or a bright blue sweater.

Another good option for a casual dinner out is to wear corduroy instead of denim. This fabric is still casual and comfortable, but looks a little more special. The Spanx straight leg corduroy jeans have become some of my favorites because they feel so good.

Since you’re dining out, you’re freed up to wear whatever kind of shoes you’d like. Remember, you create this celebration by dressing up for it a bit. No need to go fancy, but make it special.

Meet the Other Family

My parents have actually been celebrating Thanksgiving with my brother’s family and in-laws for years now. As families grow, I’ve discovered it’s quite common for different sides of families to combine for these gatherings. So I selected a few outfits that I think are perfect for meeting the “other family,” whether they be your in-laws, friends of friends or a work associate’s family.

This is a time to put your best foot forward, but you’ll still want to dress for the day. It might be a good idea to ask the host about a dress code or at least suggestions for attire. Because we do all celebrate this national holiday a little differently, I imagine most hosts would want to help you fit in with their celebration appropriately.

But if you don’t get the scoop, I’d suggest dressing simply but with some finer details. Maybe wear heels instead of flats, opt for pants or a dress instead of denim, and definitely accessorize to create a polished look.

Something like my Scotland getaway set would be perfect for such an occasion because it looks polished and elevated, but also comfy and casual. I would wear this in a heartbeat for our Thanksgiving gathering, but it require heels because the pants are so long (and I’m 5’8″).

Another good option would be this gorgeous green corduroy dress since you can easily dress it up or down.

Keys to the Meet the Other Family Outfit:

• remember that first impressions matter
• if possible, find out from the host about dress code or customs and atmosphere
• accessorize your outfit and pull it together with styling techniques
• if you’re unsure about what to wear, stick with a simple outfit, paying attention to the finer details
• dress in a way that feels authentic but special, then forget about your appearance and engage enthusiastically

Empty Nester Elegant Celebration

In the few years after our children’s graduations from college and departure from Arizona and before our own move to Ohio, James and I enjoyed making reservations at upscale restaurants in Tucson for their set Thanksgiving Day menus. I remember well wearing a corduroy skirt and boots on one occasion and opting for a pretty dress on another.

Dining at a restaurant may not be a traditional way to celebrate Thanksgiving, but we were used to unconventional celebrations by this time. And we wanted to save our travel for opportunities to be with family during Christmas if possible. Remember, a pastor can’t be gone from church too many Sundays, so we had to pick and choose our travel times accordingly.

If you choose to dine at a nice restaurant on Thanksgiving, look at it as an empty nester perk or an opportunity to experience a different type of celebration. Undoubtedly people will be dressed in a variety of ways, but take this chance to put on something very special. No one will think you look over dressed; it’s a big holiday, worthy of the extra effort. A pretty dress or skirt will help you to feel festive and all the more grateful for your blessings.

Keys to the Empty Nester Elegant Celebration Outfit:

• make the occasion feel more festive by dressing up a little
• add some color that will lift your spirits as well as those of others around you
• accessorize your outfit and pull it together with styling techniques
• wear a shoe that feels and looks a little more elevated
• consider that restaurants are often cool so dress in layers if you’re concerned

Thanks so much for stopping in for a little Thanksgiving Day outfit inspiration. The big day is just two weeks away. I’d love for you to share in the comments how you’ll be celebrating. And remember, there is no one right way to enjoy this important day. The keys are expressing gratitude for our blessings and breaking bread with someone special.

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