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Casual Winter Outfits for Women Over 50

January 26, 2024

It’s time for me to share my outfits of the week. For the most part it was frigidly cold, so my daily outfits reflect that. But by Thursday it had warmed up into the high 50s. Crazy weather! Of course I mostly work from home and then get out to go to church or run errands or maybe go out for a casual dinner with my husband. It’s a glamorous life! Let’s check out my casual winter outfits from the past week.

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How This Works

These are my real life outfits from my own closet. Many of these things are available, but some may not be. When I can locate one quickly I’ll share substitutes and/or more economical options. But if I don’t provide one and you’d like for me to, just ask.

All available items are linked in the captions of the photos. Even if they don’t look like links (sometimes they don’t highlight for some reason), they generally are. So just click through if you’re interested.

What I Wore Last Friday

Last week I remembered that I have a couple of pairs of wide leg casual cotton pants. Somehow I had forgotten about them. Ha! I pulled the chocolate raisin pair out to wear on Thursday. With wide leg pants I like to keep my top fairly fitted, so I wore a soft, ribbed turtleneck in a muted brown.

turtleneck // similar cardigan // harlow wide leg pants // boots // necklace // earrings

I added a brown belt to pull the look together, and bookended the pants with my brown Chelsea boots. During the day I wore my cashmere cardigan for a little added warmth. And I did like this look. But when it came time to go out to dinner at a favorite diner later that day I was struggling a little with what coat to wear with this trio.

cashmere sweater // harlow wide leg pants // boots // necklace // earrings // purse

Then I remembered I had this cropped length cashmere sweater. I really like this combination even more than the first because the gentle fullness in the sweater balances out the fullness in the pants, while the defined waistline of the sweater gives the look some definition. And the length of the sweater worked perfectly with the high waist pants.

How I Dressed for Saturday

Saturday we woke up to snow. So I just worked a little around the house and then spent most of the day reading. I’m reading Lynn Austin’s new book, All My Secrets. I’m on the book release team, so I need to get it read soon. You can pre-order it now and it officially releases February 6. I’ll confess it took me a couple of chapters to get hooked. But I’m loving every page of this Gilded Age story now.

micro fleece funnel top // black out & about pants // bracelet (currently unavailable) // Orthofeet house slippers // book

For my day at home I wore my black bootcut out & about pants with my clementine micro fleece funnel top. This combination felt cheerful but also casual and comfortable. Honestly, I wear my Orthofeet house slippers most all day when I’m home because I can wear my custom orthotics in them so nicely.

What I Wore to Church Sunday

Sunday we went to church. But remember, we are part of a house church and everyone dresses very casually. Still, I like to dress up a little for the most part. So I wore my wool tapered pants with a grey V-neck cashmere sweater.

similar sweater (alternative option) // tapered pant // belt // necklace // bracelet // earrings // similar boots (more economical option)

I pulled the outfit together with a black belt and stiletto booties. And I wore my Lagos jewelry on this day.

cropped wool jacket // tapered pant // earrings // purse // similar boots (more economical option) // gloves (no longer available)

It was extremely cold on this day, but I felt very warm in my cropped wool jacket, scarf and gloves. I’m wearing a size 8 in both the cropped wool jacket and the tapered pants.

What I Wore Monday

Monday we shot videos, but first I headed out to a much needed nail appointment. It was still very cold at this point, so I wore my new black mock neck from Banana Republic with my cashmere fisherman sweater over jeans.

fisherman sweater (more economical option) // black mock neck // jeans in brunch plans// boots // earrings // purse

These Ayr jeans are new and I really love the silhouette. They’re a gentle bootcut and feel really comfortable even though they have very little stretch in them. They come in other washes, too.

How I Dressed for My Day Tuesday

So yeah, I got in an order from Banana Republic. So the black mock neck above was part of the order and I got in a few other tees, too, including the white Henley I wore in Wednesday’s video. (I wore a medium in that Henley, but it is a close to the body fit.) Another item I got in that order is these Italian flannel wide leg pants. I love them.

grey Henley // v-neck relaxed cardigan // wide leg pant // sneakers (similar option) // necklace // earrings // cotton sweater (more economical option)

They’re great for an elevated stay-at-home look, but you could definitely wear them out and about, too. I’m sure I probably will. Mine are navy, but they come in a soft taupe and a grey, too. They fit true to size; I’m wearing a medium very comfortably.

For this work-from-home day I wore the wide leg pants with the ribbed grey Henley from yesterday’s blog post. It’s very soft and comfortable and fits true to size. In real life, I wore this v-neck relaxed cardigan over the grey Henley. But later when I was playing around with the look, I decided that it looks better with this cotton sweater over my shoulders (more economical option). I finished the look with my Tretorn sneakers, but you could also wear loafers, other flats or even heels with these pants.

How I Dressed for Errands Thursday

Wednesday I completely took the day off and read my book. I think I eventually did get dressed, but I didn’t take a photo. Anyhow Thursday I worked from home for a bit and then headed out to run some errands. It was rainy and unseasonably warm. So I wore this lush longsleeve tee from Ayr with my J.Jill jeans.

tee // jacket (not available in this color)// jeans // similar sneakers (more economical option) // earrings // chain necklace // compass necklace

This relaxed but sporty combination felt perfect for the rainy day out. I actually didn’t even need a coat or jacket. But while I was at the mall I made my first purchase for my upcoming Alaskan cruise and land tour (in late May): this icy blue long trench jacket from Athleta. The sales person said it’s new and has been selling like wildfire, but I don’t see this color on the website. Maybe it will be available online soon. It fits like a dream true to size and it checks all the boxes: it’s lightweight but lined, has a hood, zips and snaps, has comfortable side zip pockets and is 100% waterproof (but doesn’t have that heavy waterproof feel at all). The jacket does come in black which would be really chic, too, but I think this soft grey-blue will be nice for the spring.

By the way, if you’ve been to Alaska in May and have any suggestions for how to dress, I am so open to those. We will be on a nice cruise line, so I’ll need to wear some elevated but still casual/sporty things for that. But I really need help with what to expect weather-wise in late May. I’m assuming it will be quite chilly still.

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Blessed for My Day

This week in my Bible reading I came across Genesis 50:20 and Matthew 16:22-23 on the same day. Both scriptures spoke to me about the importance of seeing life through God’s perspective rather than just through my own desires, emotions or plans. When we consider our relationships, happenings, interactions and circumstances from God’s vantage point rather than just our own, we see things very differently.

That perspective also actually makes us more useful to God. Like Joseph, God is able to use us to accomplish His purposes and we bring Him glory. Finally, when we look at life from God’s purposes and not just man’s we have more peace and joy. Do you need to reconsider something that is going on in your life, this time looking at it through the perspective of God’s purposes?

“As for you, you meant evil against me, but God meant it for good in order to bring about this present result, to keep many people alive.” ~ Genesis 50:20

And yet Peter took Him aside and began to rebuke Him, saying, “God forbid it, Lord! This shall never happen to You!” But He turned and said to Peter, “Get behind Me, Satan! You are a stumbling block to Me; for you are not setting your mind on God’s purposes, but men’s.” ~ Matthew 16:22-23

xoxo, Kay
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37 thoughts on “Casual Winter Outfits for Women Over 50

  1. My husband and I are just starting to look at Alaskan cruises for the August timeframe. I would love to know which cruise line you decided on.

    1. We’re going on Regent. We definitely wanted something smaller. And since this is a big celebration of our 60th birthdays, we also wanted something luxe.

  2. I’ll be following along as you plan for your Alaskan cruise! We’ve also got an Alaskan cruise booked for late May and I’m wondering what the weather will be like and what to pack (without overpacking ; I do know that we’ll have lots of daylight!

  3. We did an Alaskan cruise in June, and I was so glad I packed a down filled puffer jacket, hat, and gloves. Also recommend warm socks and waterproof footwear. ( Teva sneakers worked great.) Sweaters and sweatshirts you can layer will also keep you cozy. Your shore excursions may take you to a glacier or native village – always a bit windy too. I would also recommend extending your stay with a train trip from Anchorage to Denali. Our cruise was Royal Caribbean, and very informal. Lots of multigeneration family groups. Your trip,will be memorable, I promise!

    1. Thanks for all the tips. Yes, we are extending our stay, but have opted for a driving tour. We want plenty of time for James to be able to take photos at his own pace.

    2. Good advice! We’ve been in July and August and were very chilly! And wet. Snug hat, gloves, long underwear and waterproof clothing helps. Shorts and short sleeves for the hot days but we rarely wore them. Binoculars are a must! If you don’t have good ones, they often have nice ones for purchase on the ship, high quality. Can’t wait to hear about your trip!

  4. Too funny. Hubby and I also have a late May cruise booked to Alaska! Not sure what you mean by a “nice cruise line” as they all seem to be nice. We do a lot of cruising! I live on the west coast of Florida so don’t have a lot of warm “winter” clothing. Watching for end of season sales. Elegant nights are my concern! My closet of sundresses may not work for Alaska elegant nights!

    1. We’re going on Regent. While dress code requires that James wear slacks and a collared shirt, we don’t plan to dress up especially. I will take one to three lightweight dresses and James is not planning on taking a sport coat or blazer. He’ll just stick with button-up shirts and polos. I know you’ll have a wonderful time, too. Stay tuned; I’ll be sharing my packing list as I prepare for sure.

  5. Love your “what I really wore” posts! I’ll be retiring in a few months and I’m determined to do my best to look “put together” at home every day in retirement – whether or not I’ll be getting out of the house. So your “real outfits” are very helpful to me! Thank you! Enjoy the Alaska cruise – we went on one in July so not sure I can help with what to wear weather wise. But the scenery is so gorgeous. We did a couple of beautiful hikes and also did a whale excursion that was just incredible!

  6. Your daily outfits are all so lovely and reflect your style for sure. The big pants are still a hard silhouette for me to appreciate. As for Alaska in May, that is when we did our trip a few years back. It was cold, with some rainy days and sunny days. The only time I was really frozen was at the glaciers – like standing in an ice cube! Most of the time the seas were calm with a rough crossing to Seward which was most unsettling. The land part of the trip was wonderful, on the train and bus. This was a trip of a lifetime and I really can’t wait to go back. Your really cute trench jacket will be perfect – layers layers layers. Don’t stress on the dressy outfits, one or two will suffice. Alaska is very casual. Enjoy!

    1. Thanks for the scoop, Penny Jo. Yes, I thought maybe 1-3 lightweight dresses and then a pair of nice slacks for dinners. We’re not going to dress up very much.

  7. Hi Kay
    When we took our Alaskan cruise several years ago we packed one large each bag which we checked, and a carry one with outdoor clothing for our land days. You will need jeans, good walking shoes or hiking boots, sweater, lightweight parka, our cruise line had 2 of their own hotels in Denali for our stay for 2 nights. Excursions during the day you will need to have casual clothes and when you cruise into the glaciers you will need gloves, wool cap, sweater your lightweight parka. It’s magnificent ! Have a most wonderful trip.

  8. We did a Holland America land/sea cruise from the middle to end of May 2022. The smaller ship catered to an older group. We fit the demographic. The weather was lovely and only one day with a light rain, although our wilderness guide said it had been very cold just the week before. My normal puffer jacket was sufficient. The only really frigid weather was in Glacier Bay. It was not a very dressy group even on the designated dressy evenings. I wore black dress pants with dress shoes, small clutch and dressy jewelry and just wore different somewhat dressy blouses for those evenings. I was perfectly comfortable and dressier than most. I only saw one older lady with a lovely long gown and thought “someone’s granddaughter got married this year.”

    1. Sounds like a plan. I had thought I might carry one or two lightweight dresses I can easily pack and a pair of slacks. But when push comes to shove I may just do the slacks and blouses like you mentioned. Sounds good.

  9. Hi Kay,
    Layers, layers, layers. Good walking shoes are essential for any excursions. We had exceptionally warm weather in May when we cruised 2 years ago, it’s was 70-75 every day with no rain at all. But when the sun goes down at 10pm it does get cold, mornings too. The cruise line told us that was definitely not the norm! I dressed up for dinner every night in a pretty dress or fancy pants. This May we are headed in the opposite direction to Bermuda.

  10. Nice outfits. I’m interested in your Alaskan cruise too. I plan to go with my son’s family when my grandson graduates next year. It will be in June. I’ve wondered what to wear. Good tips on the comments.

  11. Hi, Kay! My husband and I will be cruising to Alaska in May as well, but our trip is early May. We are so looking forward to it! I’d love for you to share more about what you will packing as you prepare in the next few months. Have a great weekend!

  12. On our Alaskan Cruise in May we just had fleece jackets and we were fine. A rain coat in Alaska is always and good idea, so just layer up on whatever excursions you plan to do. We walked a lot at each port we stopped in. Had a great time.

  13. I actually have been to Alaska in May! I don’t know if it was because of the amount of light, but it was warmer than I expected. Fairfax was cool. We went for a walk in this GORGEOUS park with birch trees-probably my favorite hike (Haines a close second). Denali was chillier. I suggest layers and tha coat is perfect. Kayaking to see the eagles in Ketchacan (spelling?) was freezing. Lots of rain there. Hope that helps! Have fun!

  14. Hi Kay….my husband and I Love to Cruise 🚢 and have been on an Alaskan Cruise and we have also flown there to Kodiak, AK always in the month of July because that’s when the salmon are spawning. I would recommend taking long sleeves because it’s always cooler on the water. Also take a rain jacket just in case. The weather is “iffy” in the month of May I would think. It will be an amazing time though.


  15. That pale blue Athleta coat is PERFECT! Perfect in every way! We went on an Alaskan cruise years ago and one of my strongest recollections (from our pictures) is ….”Did I wear the same nasty white hoodie every single day???” And I practically did!! We went in the summer and this was back when we weren’t phone savvy so I had no clue how to research the weather! And it was afterall summer…. I had actually just thrown that hoodie in for walking on the deck! I don’t think I ever did take it off!!! So YAY for that classy-looking Athleta jacket! You will wear it a lot! And I can just imagine how so many tops will look fantastic under it! PLUS… it is most definitely in your color! It looks great on you!! So bottom line, my advice is to forget it’s summer!! Think windy and pack to stay warm…. be it on boat or land!

  16. Hi Kay, I went to Alaska in May in 1994 and 1996 (cruises: first, Inside Passage round trip from Vancouver, second Anchorage to Vancouver) – would love to go back. Alaska is spectacular, the air is crystalline. If your lovely jacket is truly waterproof, that’s one item checked off. I’d also bring a hooded, zip front sweatshirt. Waterproof shoes are a good idea, I love my waterproof sneakers from Merrell. I found that the temperatures ranged from 45 to 80 degrees, so layers are certainly what is needed. You need to be prepared for changing weather conditions, and be comfortable on any excursions, but bring good quality items and don’t weigh yourself down. The mosquitos are not quite “the state bird” yet in May but I’d bring some bug spray anyway. As far as dressing up on a cruise, I’ve always found that a pair of good black slacks and a variety of tops and scarves or jewelry go far in creating the look of multiple outfits (a black merino wool top and pearls with the black slacks is certainly enough for a dressy evening). I can’t believe it’s been so long since I was there but I’m sure that Alaska is still as awe inspiring as I remember. Have a wonderful time and say hello to all the magnificent soaring eagles for me!

  17. I cruised in Oct. on Celebrity Silhouette, I found layers to be best. I wished I had brought a jacket for rain. It was the best cruise we have taken so far.

  18. I commented in your “Contact” specs on your blog. Sorry! We cruised to Alaska in 2000 in early June. I agree with other commenters who said to layer your clothes. The athleta jacket should work well, as long as you have room to layer sweaters, fleece jackets, down vests underneath. A warm hat and gloves, sturdy, waterproof walking shoes//boots (Merrell and Keen have good options), are essential for on shore excursions. On board days are good for more elevated basics, layered. A dressy pair of black slacks with several nicer tops would be fine for dinners. My parents took all three of us kids, our spouses, and the ten grandkids to celebrate their 45th wedding anniversary. It was a fabulous trip! Do plan on rain and cold, especially near the glaciers. Have a wonderful time.

  19. Kay,
    You will love your trip to Alaska, as long as you are prepared for the weather.

    Take layers from thin insulated long underwear, a thin quarter zip patagonia on top of this, a warmer base layer,, a down jacket to a TRULY waterproof coat AND rain pants. Be able to wear all the layers under your Rain Coat and Rain Pants. (Rain pants that easily snap or zip over you existing pants work the best.) And of course thin gloves to WARM winter ski gloves. Warm boots you can hike in. And a back pack to wear on excursions that you can tuck the layers in as you take them off and put them back on again. I think the oversized rain coat to wear on top no matter if it is drizzling or a downpour is the key. But, I am not dressing for fashion – I do not want any weather to stop me from experiencing this most amazing beautiful area.

    And then if you have warm gorgeous sunny weather – Hallelujah!
    (And you will be all outfitted for a trip to Patagonia :))
    Enjoy, Tammie

  20. Your Alaskan trip will be wonderful. I am glad you are doing the cruise and land tour. Many folks only cruise and miss the massive land that compromises Alaska. Our son lives in Anchorage, so we are privileged to visit there several times yearly. We just returned from celebrating his January birthday with him in a winter wonderland. You have received some good suggestions. I will add that attire in Alaska is very casual. People dress for comfort rather than the latest trends or styles. Several must haves are rainwear and comfortable shoes for exploring. The temps in May may be in the 50’s, and it is always cooler on the water. I always take too many clothes and usually wear things several times for comfort and warmth. As has been said packing layers is smart. You will see some of the most beautiful of God’s creation there as you cruise and drive in Alaska. If you have any time near the airport in Anchorage the largest seaplane base in the world is located nearby where you can watch sea planes take off and land on Lake Hood. It is an important mode of transportation to the remote areas of that vast state.
    There will be lots of daylight as the summer solstice approaches in June. Most places to stay have black out curtains so you can sleep. I am very excited that you have chosen such a beautiful place to visit.

  21. We celebrated our 25th anniversary with my dream trip – to Alaska! It was a land tour, followed by a cruise, and like you, on a smaller ship. It only had about 800 passengers and catered to a slightly more mature patron, so my husband and I saw no children, and no fun things that children are drawn to. It was very relaxed, and personal.

    Many of the activities were things that we learned about ALASKA. The first day, we chose the activities we wanted. On one excursion, we rode a plane over the Arctic circle and on the way there, we stopped at a village of residents. It’s was such a delight to mingle with them. In fact, there were some young girls, probably 9 or so, and they were selling some jewelry that they made, and it was worth the smiles on their faces to purchase their work.

    We rode a helicopter to a glacier – I took a photo of my husband with his hand in the clear water, we visited a dog camp, the Mendenhal glacier, went whale watching on the ship, because when on the ship we still got to take excursions.. We purchased a package that included a ceremony in which we repeated our vows and had a nice dinner in their fine dining area. Normally the ceremony involves all couples who were on the ship (and signed up for the ceremony) but it was just us and the Captain, so we had the opportunity to talk to him for at least a half hour. It was a Holland-America line and I hope he enjoyed our company.

    We went in July, and happened to be on train the day of my birthday, so of course we got a cake and I blew out a candle. I thought that was very thoughtful of them.

    Went went to Susan Butcher’s dog camp (Iditarod winner), went to a salmon campout.
    We did more and if I think of them, I’ll let you know.

    We dressed nice on the ship when we knew we were going to be on the ship, every day we did something that we needed to ‘dress for the weather.’ It was in July, and temps were about 75 in the day time, and it never rained – so it was perfect. However, people post their pics of their current trip, and it doesn’t seem to be nearly as cold, because so much of the snow, and ice, has melted. I suspect May will probably have days similar to what we had (we were told it’s colder in the spring) We had heavier jackets and wore them a few time. Jeans were not out of place and I did take gloves that I wore, usually if being off the ship in the morning.

    Right now, that’s all that I can think of, though I’m sue there was more. Have a beautiful anniversary, and let them pamper you!

  22. Hello Kay… I too am tall and usually wear a size medium. Would you tell me what size you purchased in the Banana Republic mock neck? I am unsure if I should order the medium or large mock neck in brown….appreciate all your work here at Dressed for my day!
    Thank you,
    Ann Marie

    1. I am wearing my TTS medium and am happy with the fit. It is a close to the body fit, however, so if you’d prefer something looser I’d go with the large.

  23. We are cruising to Alaska in June! On a Holland America ship. This is great I can follow you to help us get dressed and pack for this trip! I am going to start shopping for good walking booties now. Maybe I will get a sale. Thanks for all you do Kay!