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Thanksgiving Day Outfit Ideas for Women Over 50

November 14, 2023

Mind you, I’m not one to think that women over 50 have to dress differently than women under 50. Ha! But I know that a lot of women put that phrase, “Thanksgiving Day outfit ideas for women over 50” into a search engine hoping for a little insight that does take into consideration their maturity and station in life. And there’s nothing wrong with that. I definitely do dress a little differently than I did just 10 years ago. But regardless of your age or stage or whatever, I’ve got some Thanksgiving day outfit inspiration for you here. I’ve rounded up some of my favorite fall outfits from this year to spark our imaginations a little.

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I think many of us dress fairly casually for Thanksgiving dinner. But let’s start with the dressier outfit ideas for Thanksgiving. A simple, comfortable, but also classy skirt could definitely work. The elastic waistband on this pleated skirt makes it a great choice.

Styling a Pleated Midi Skirt 2 Ways for Fall
pleated midi skirt // shrunken sweater // suede block heel pumps, (Use code SARAHFLINT_CCLAURAKAY1 for 15% off at Sarah Flint, new customers only) // necklace // earrings (similar) // bracelet // similar clutch

This velveteen shirtdress is definitely roomy enough to eat heartily in. Ha! Let’s face it; room to eat well is a priority for me at Thanksgiving.

Corduroy Jeans
velveteen shirtdress (runs large) // similar boots // necklace // similar clutch // earrings (use code KAY15 for 15% off your purchase at Penelope Jewelry)

The velveteen shirtdress does run large. I’m wearing a medium, but I really should have had them take the small off the mannequin because it would have fit me better.

floral printed dress // boots (alternative option) // necklace // earrings

 This floral printed dress could be worn with boots or flats. It’s really fun to wear and a definite contender for a slightly dressier Thanksgiving outfit. It also runs large; I’m wearing a small here.

And before we go on to the non-dress options, let me share one idea that is definitely a little more elevated. I have had readers tell me they are going to their country club or other restaurant for Thanksgiving. James and I have done similar things before and I usually wore outfits like the ones above. But in case you need something even dressier (for Thanksgiving or any other time) I can highly recommend the dress I wore to the LTK Con awards banquet.

Maggy London Metallic dress

You’ll have to check out the Maggy London Metallic dress at the website to see the colors in this lovely faux wrap dress better. It’s very comfortable, but also quite elegant. And I think the colors make it really nice for fall and winter.

Add some color to your appearance with makeup.
black pants // turtleneck // black pumps (use code KAYHEELS for $50 off your first pair of heels at Ally) // coat // brooch // pendant necklace // earrings // lipstick in Rebellious Rose and blush in Rebellious Rose and lip pencil in Rebellious Rose

I think classic black trousers with a classy turtleneck is always a good combination. This is a no-fuss, elegant look that is still classy and comfortable. For a slightly less dressy look simply swap in loafers or ballet flats for the pumps.

Party Outfits
black pants // woven sleeve v-neck pullover // ballet flats (use code SARAHFLINT-CCLAURAKAY1 for 15% off your first full-price order at Sarah Flint) // earrings (use code KAY15 for 15% off your purchase at Penelope Jewelry)

The outfit above is one of the holiday party outfits I shared in a recent post. Those black pants from Spanx are slimming, but still comfortable. I do suggest sizing up; I’m wearing a large. The woven sleeve v-neck pullover is one you could wear all holiday season.

red cowlneck blouse
plum wine silk cowlneck blouse (more economical option) // necklace // earrings // Veronica Beard Somner Dickey jacket (more economical options below) // similar black jeans // black Ally leather booties (Use code KAYBOOTS for $50 off your first pair of Ally boots.) (more economical option)// convertible satchel bag (more economical option)

As we move toward a little less dressy outfits, let’s consider black jeans. They’re a smart choice because they look elevated but feel like, well, jeans. You can top them with a pretty blouse and jacket for a more elegant look…

Jeans and Sweater Outfit
jeans // booties sold out // cashmere crewneck sweater // necklace // earrings // bracelet

or wear them with a pretty pullover sweater for a more casual vibe. But this outfit still looks polished and pretty, especially with those pointy toe booties and the trending fuller leg jeans.

Create pleasing neutrals combinations.
quilted jacket // jeans sold out // shrunken sweater // boots on left similar // Tish Chelsea boots on right // necklace (optional necklace) // earrings // bracelet

But dark wash jeans in a low contrast in intensity outfit can look just as sharp. I love combining dark denim with brown for a moody, elevated vibe.

Add some interest to your all neutrals outfit.
black pants // leopard socks // similar loafers // denim button front shirt (TTS; wearing medium) // quilted barn jacket // sweater // necklace // Tish Chelsea boots // earrings // jeans

On the left above I’ve created a classy but casual look with my black Tribeca pants and a denim button front shirt. And on the right I’ve created a similar look but with dark wash jeans and a pullover sweater. I think that owl sweater might be especially appreciated if you’re celebrating Thanksgiving with little grandchildren. I wore it when I taught children’s Sunday school this past week and the kids loved it.

Jeans and Sweater Outfit
Alice Walk Cape // jeans (TTS) // sweater in undyed stone (TTS) (more economical option) // booties // necklace // earrings (use code KAY15 for 15% off your purchase at Penelope Jewelry)

The outfit above is one I would definitely wear if I were going to a friend’s house for Thanksgiving. It’s polished but comfortable. It’s easy on the eyes and very autumnal. But if you prefer higher contrast in intensity in your outfits, you could wear something like the jeans and sweater pairing below.

Favorite Winter Outfit Formula
dolman ribbed sweater in cream (TTS) // stretch bootcut jeans // sugar Envoy booties // earrings // similar necklace option

I think nice jeans and a simple but polished sweater is a great outfit formula for Thanksgiving day. But if you fear that the jeans may be under dressed, swap in a pair of black pants instead, like I did below.

Cashmere sweater with Tribeca Pants
Audrey cashmere Donegal sweater // Tribeca pants // necklace // loafers // earrings // bracelet not available (substitute)

Here are a few other great jeans outfits for Thanksgiving.

Jeans outfit for Thanksgiving
 sweater in undyed stone (TTS) (more economical option) // jeans // boots // earrings // shoulder bag // jacket
jeans outfit for Thanksgiving
jeans // boucle cardigan // boots // earrings
jeans no longer available // tank // flannel shirt // loafers // necklace // earrings
casual fall outfits from JCPenney
mid-rise straight leg jeans in dark formation rinse (TTS; wearing a misses 10) // black tank (similar) // plaid flannel shirt (TTS) // black belt // black Chelsea boots // necklace // earrings // bracelet

And finally a few non-jeans options that are still casual and comfortable. First up, my favorite wide leg trousers.

cardigan // antique cream ribbed top // brown Harlow pants // belt // croc Mary Jane sandals // purse // necklace // earrings (use code KAY15 for 15% off your purchase at Penelope Jewlery)

Above I’m wearing the Harlow pants in a pretty chocolate brown with my croc Mary Jane sandals. I topped the look with an antique cream ribbed top and a simple cardigan. So this outfit looks a little more elevated than a jeans outfit, but it feels just as comfortable if not more. And below I have a very similar outfit with the Harlow pants, this time in a khaki shade.

Harlow wide-leg pants // white tee // cardigan (similar 60% off) // earrings // necklace // loafers (another option) // belt // bucket bag // loafer

Next, I’m a big fan of corduroys on Thanksgiving. They just feel very appropriate to me.

styling cords for favorite fall outings
denim button front shirt (TTS; wearing medium) // stretch corduroy straight leg pants in almond buff (TTS; wearing a 10 comfortably) // Tish Chelsea boots // skipping stones stretch bracelet // earrings // crossbody saddle bag

But if you’re staying in and keeping the day super casual, then I suggest putting together a polished outfit of athleisure or activewear.

woven trim jacket // top // pants // sneakers // necklace // earrings // bracelet

And here’s another similar option.

T by Talbots
sherpa jacket // top // pants // sneakers // necklace // earrings // bracelet

Between the two jackets I wore with those outfits, I’d say the sherpa jacket above is my favorite and the softest, coziest.

Thanks so much for dropping in. I hope you got a little Thanksgiving Day outfit inspiration!

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Blessed for My Day

Today we can praise the Lord in various ways. We can verbally tell Him who He is. “Lord, you are holy and high and lifted up. Praise You that you are like no other and there is no other like you.” We can praise Him through song, singing along with praise songs or hymns. And we can praise Him to other people.

While I think it is very important – commanded even – to praise God directly, it is such a living testimony to sing His praises to other people. I like to do that simply by bragging on Him in my normal conversations. I may say something like, “We are so grateful that God has provided for us so that we could do this for you. God is faithful to us, and oh so generous. So we wanted to be generous to you.” How will you praise the Lord today?

I will give thanks to the Lord according to His righteousness And will sing praise to the name of the Lord Most High. ~ Psalm 7:17

xoxo, Kay
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9 thoughts on “Thanksgiving Day Outfit Ideas for Women Over 50

  1. Thanks Kay! You’ve given me some ideas for Thanksgiving. I’m always debating whether or not to wear pantyhose with dresses that expose your legs. Boots are a great option to avoid the issue, but what about if you want to wear a pump and it’s a dressier event?

    1. I think it’s fine to wear sheer, nude hose with pumps. Just don’t wear them with sandals and I prefer they not be worn with sling backs either. But that may just be me. 😉

  2. Thanks, Kay! I love all of these options. We will be meeting our family in the N. GA mountains. We’ve rented a house in Blue Ridge. So we will probably be wearing sweaters, jeans and boots, my favorite!

  3. What is the color you have on of the fisherman’s sweater in the picture with the brown jacket? The brand is Quince and I can’t tell if it is Oatmeal or Camel.

    I like all of the outfits that you did. We are casual for Thanksgiving so jeans and a sweater are good for me.

    Thank you.

  4. I also have a question about pantyhose, even though it’s not directly related to Thanksgiving. I recently purchased a black dress that I will probably wear with black pumps to funerals and possibly dressy restaurants. Should I wear nude or black pantyhose with this outfit? I read somewhere that it is inappropriate to go with bare legs to a funeral. I apologize for getting a little off the subject! I do appreciate all of your great advice.

    1. I think that rule is out the window unless it is for a particular funeral venue, such as a church that requires covering. However, if you feel you should wear hosiery that is perfectly fine and you should definitely do what you feel is best. I think either option is perfect – black or nude – and you could create very different looks depending on which you choose. If you do choose to wear black hosiery then I would opt for black shoes, too.

  5. The cool beiges in the tonal outfits look amazing on you Kay! That bronze dress is next level. What would you wear as a layer over the floral dress if you needed to? Would you do a post on what to layer over dresses for those of us who get chilly but still like to wear the cute dresses? I am deterred from wearing them in the winter because I feel limited by a suitable top layer.