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Winter Fashion For Women Over 40

Happy hump day and welcome to my winter wonderland! I might sound positive but it’s just an act. This weather is killing me! The snow is deep and I woke up to more snow falling and our temperatures are plummeting to -11 by tonight. Fun times!

Winter Fashion For Women Over 40
I’m sharing some more winter fashion today. I’m sorry to all my warm weather readers. Those of you who live in the deep south or out on the west coast, are not dealing with this winter weather.

The snow stopped yesterday for a while, and I headed out of the house to pick up a few things. Basically, I had been in for 2 days straight and I had to get out!

My goal was warmth and as much as I hate to admit it, fashion wasn’t the highest priority. I miss wearing my booties and heels.

Winter Fashion For Women Over 40
I wore this cardigan back in October when I was doing 31 days of fall fashion. This picture makes me miss green grass!!

Winter Fashion For Women Over 40
Winter Fashion For Women Over 40

Striped cardigan-Stitch Fix//White top-J.Jill//Skinny jeans-Tommy Hilfiger//Ugg Boots-Zappo’s//Earrings-Stella & Dot//Scarf-Walmart

Since I’m stuck at home, I’ve been doing some online spring shopping! I’m gearing up for March. I took the plunge and bought a pair of Converse Sneakers.


These are going to be a little out of my comfort zone but I’m hoping to share how to wear them for women over 40.

I would take a heel over a pair of flats any day! Mules are making a comeback and I love them! I will hopefully be styling a pair in March.

Do you like flats or heels better? Of course, the heels need to be comfortable!

I’m going to be pinning a lot of spring fashion so make sure you follow me on Pinterest. You can also find me on Instagram, and Facebook.

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Beauty For the Heart~~We are here at this time at this season for a reason! God has a purpose for your life and he wants to use you in kingdom work. Don’t forget that!

This generation of Christians is responsible for this generation of souls on the earth! -Keith Green

Have a blessed day!


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  1. I had to chuckle when you said you were online shopping for Spring. I skipped Spring and went straight to Summer and bought 2 bathing suit coverups online yesterday. I am “virtually” getting ready for pool weather!

  2. Hang in there Cyndi!!!! We are currently in the San Fran area of CA, but we spent 3 LONG winters in Minneapolis (2010-2013), so I know EXACTLY how you feel. Look on the bright side, by next week you guys might thaw out, we would have snow (and lots of it) on the ground for 7 straight months…UGH!!!!! I do appreciate the weather here everyday!!! (but I’d move back to the SOUTH in a HEARTBEAT if my husband found a job there) I L♥VE reading your Blog everyday!!!!

  3. Oh Cindi, what a darling outfit! So put together and beautiful against your heavy blanket of winter snow! I had no idea your neck of the woods got that kind of snow! I’m gearing up for Spring also! My tulips are poking their heads out of the ground which prompts me to poke my head out to purchase a few springy outfits! 😉

  4. Cyndi, we’re covered in winter too over here in MO…….my leg is healing slowly and I can just now get into my Uggs so I thought I was doing pretty good till you start talking spring…..LOL
    I will be able to pull off the converse tennies far easier than I will the mules for spring this year……so I can’t wait for ideas to come into your very creative mind! At least we have beautiful sunshine at 11 degrees!
    Love, In Him, Marcia

  5. I too am done with winter and ready for spring. As much as I like my boots – I’m tired of wearing them…. needless to say I also just bought a pair of white converse but I think I need some sort of arch support as this style of shoe is just too flat for me but I sure to love the look. Heels vs. flats….well, I like comfortable wedges and flats with the elastic/comfort backing.

  6. I prefer the comfort of flats, but I like the look of heels….they make me taller and (I think) slightly slimmer. I hope you will find some really comfy heels (I need to try platforms, hear they’re better) to share.

    1. If Land’s end still has them their “Chukkas” with rubber soles and a little height have been a great comfortable alternative to heels for me. Try walking a bit in your platforms before you buy-there is NO flexibility in the shoe whatsoever. I love a heel but I cannot do platforms.

  7. Flats here. I’m always running around, doing housework, laundry, dishes, dropping kids off and running errands – I just don’t see the point in wearing heels. They slow me down!

  8. I prefer heels but my feet do not allow them except for rare treats. There are some really wonderful flats available though, so I guess I can’t complain. Converse makes a leopard print sneaker which is very cute but I like the Vans version more (no white toe with the black and tan). Chucks are classics and women over 40 can assuredly wear them stylishly. Keep you chin up about the weather if for no other reason than to keep your nose above the snowbanks. 🙂

  9. I love your outfit Cyndi! I like both heels and flats. Just depends on what my day will bring. Looking forward to your “spring line” 🙂 and I love mules too! God bless 🙂

  10. Love your outfit and the beautiful white blanket of snow is such a treat to see! I now live in Texas and miss the snowy winters of Michigan – but not the 5 months of frigid temps!! I so enjoy your daily posts! Thanks for sharing your talent with us!

  11. Love the look!! I also love heels but my back prefers flats or a small heel. As I have aged, I spend more on shoes for comfort and try to buy cute too! I really do not do tennis shoes or Converse, except for exercise! I think you would really rock Converse!!

    1. Soma vanishing line panties. They frequently go on sale buy three get two free. No ride up, no panty lines, good coverage if you buy the modern brief style.

    2. I am a curvy girl and found that my panties were always riding up until I found Warners No Wedgies, No Worries. They don’t ride up, even when I am working out. Check them out at Kohls.

  12. I, for one, appreciate your cold weather posts since I’m looking out my window at piles of snow! Your blog is my first and only that I follow. Love it!

  13. Love the outfit Cyndi!! My preference is heels. I’m 5′ 3 1/2″. and overweight. My entire family if tall so I wear heels so I’m not so short next to them. Plus I think flats emphasizes my weight. I don’t like wearing flats with jeans or dress slacks. I wear boots and booties most of the time. During the summer though, I live in flip flops (and dream of being at the beach!!)`

  14. good morning. having completed our 7-10 days of Winter, I am really enjoying looking at your beautiful snowscape photos. I liked the outfit in both seasons.. How great to show the versatility of some articles of clothing in your wardrobe. great example for all of us rather than just reading about it. Does anyone else have leg cramps from the soles of shoes without some arch support ???

  15. I’m surprised by all the negative comments regarding heels. Well, not negative, but that you all don’t wear them. It just takes getting used to and a proper fit, unless of course there is a medical reason. My 80+ mother (can’t give exact age for fear of my life) had knee replacement surgery. In 7 weeks, she was rocking a kitten heel. My mother….think Julia Sugarbaker in her 80s. (Yes, she is also from Georgia.) Seriously, though, I find that rotating the height of the heels I wear is actually more comfortable than flats every day.

    Cyndi, you look precious as always. The snow looks lovely but I cannot imagine actually dealing with it. A 4 day ski trip is about all I can handle.

    Sending warm hugs from the TEXAS gulf coast!

  16. I love a good heel (prefer wedges) but I also enjoy a fabulous flat. Mules — eehhhh — only because I find them harder to keep on than heels with straps. I’m not really a pump girl – I prefer the t-strap shoe. To put this into perspective, I work downtown and have a hike to my car to and from work and I’m 53.

  17. We are dealing with record lows and ice/snow/sleet here in NC too. It is supposed to be 0 tomorrow morning when we leave for school. I’m not looking forward to that. My daughter has to wear a uniform, and her poor legs will be freezing with only tights. Come on Spring! 🙂

    I prefer flats or chunky heels. I cannot wear traditional pointed toe pumps anymore, as my foot problems/bunions get worse with age. I have had bunions since I was 14, and I keep putting off surgery because I think I would die if I couldn’t workout for 6 weeks! I know….I should have the surgery and wear cool shoes afterwards. Or I’ll just live vicariously through all of you. 🙂

    1. My neighbour had the surgery and now delights in painted toes and cute sandsls. I don’t think you would be sorry.

  18. Out on the west coast we are shopping for spring. I went through my closet to purge and narrow down the must haves for my wardrobe. It’s really, really hard to stick to that list though. Too many pretty things.
    I bought a pair of converse last summer but don’t find them particularly comfortable. I think I’ll add a Dr Scholl insert and see if the cushion helps. I bet you’ll rock them!

  19. I love looking at the snow from my vantage point- on my computer screen! No need to apologize for the winter wardrobe- here in sunny south Florida we are having (our version of) freezing weather! Your outfit today would be perfect today, but the Uggs are a once or twice a season rarity- by afternoon we’d be sweating and have to switch to flip flops! But not tonight- tonight they’d be a dream! We love the chance to get warmed up and throw on a scarf down here, so I enjoy your wardrobe- from my computer!

  20. Love your outfit & the background for the pic is sooooo pretty! You’re getting lots more snow than we are! I love comfy flats and a wedge with a shorter heel…I have gotten pretty clutsy as I’ve gotten older. Can’t wait to see how you style the mules, i used to love wearing mules. Have a blessed day 🙂

  21. We just got 15 inches here in your neighboring state of WV! I love my boots, but it has been so doggone cold here (-15 tonite), that I have not ventured out of the house since Monday. You look very cute in your snow day ensemble!
    Love heels! They just make everything “hang” better. To me, however, there is just boot season , then sandal season. I just don’t care for the shoes that come in between!

  22. Living in Ga, we don’t get much snow. However, we’re expecting below zero wind chills Thurs. Your snow pictures are beautiful, but hopefully this will be the end of the snow for you!!
    I wear a mixture of heels. Being 5’3″, I’m in shoes with more of a heel. I’m not a fan of the lace up sneakers, but have my eye on a pair of leopard print slip on sneakers. I’m so happy to see mules making a comeback, love the tan ones you posted! I’m ready to put the boots away and open up my toes! I love all your looks today, and a BIG thank you for braving the cold for us!!

  23. Yep our weather here in the northeast corner of Indiana is the same. I’m SO over this!
    I’m excited about your converse shoe purchase! I just purchased some myself. Of course my 18 y/o daughter wasn’t that thrilled about them.
    She said, “umm…nice shoes. I would wear those. Those are for teenagers.” (insert eye roll)
    I said, ” you wear “mom” shoes.” (she’s always in my closet)
    She said, ” I can get away with more things because I’m young.”
    Teenagers! Lol!
    Hello, I’m 40 & my life is over! Where’s my rocking chair?! :/

  24. To tell you the truth, I like seeing snow in your background because I was so very jealous of your grass backgrounds for quite a while. Love the outfit! Looks warm and stylish!
    Up here in Ontario, Canada it was -40 for two days over the weekend and the only time I went out was to go to church. I will be so glad to see spring come!

  25. I love the snow. I always look at it in a different way I guess. When I see how white and beautiful it is, I can’t help but to think of how it covers up everything that is ugly and dirty. It makes me think of how much Christ loves us and will take away all the ugly and dirty things in our lives if we only ask Him to.
    Cyndi, you look pretty as always, no matter what you wear.

  26. I bought some converses at the end of summer and I love them!!!! I wear them so much more than I thought I would. They are so fun and make me feel young!!!! I love your blog and copy so many of your looks. Thank you!!!!!

  27. I’m loving that you ordered Converse. I was going to ask you what you thought of them for women over 40 or 50. EEK! I can’t wait for you to style them. 🙂

  28. Who says you can’t or shouldn’t wear converse if you’re over 50. I own 3 pair, black, pink but my favorite are my leopard. Love the snow. I live in sunny Florida and we are expecting to get in the 30’s tomorrow.

  29. I bought a pair of converse sneakers and think they will look cute with ankle jeans and casual wear. Eager to see how you style them!

  30. Hi, You say… “fashion wasn’t the highest priority” … but you nailed it, Girl!!!
    You look cozy warm and very chic!! I think warmth and fashion can go hand in hand!
    Love this ensemble! Keep styling for us… giving us very good helpful tips… and beautiful Bible verses to remember!! Cyndi, YOU are an inspiration to all women! <3

  31. I bought my first pair of converse last summer and have just enjoyed them so much, we have had some warm days in Shreveport La so I wore them with my distressed boyfriend jeans and a gray navy striped short sleeve t-shirt! I love the look and feels to me age appropriate or at least hope so, love seeing the choices you have made I’m inspired to try new things!

  32. Love this look! Comfy, cozy & classy! It’s been below zero here in upstate NY for what feels like forever (right now the wind is howling and it’s around -30 with wind chill) so it’s been hard to look stylish and be warm! However, I’ve been taking notes!! Styled some sweaters with warm infinity scarfs and must say..my hubby even commented on my “new look”! 🙂 thanks for the inspiration Cyndi!