25 Winter Outfits // Fashion Over 40

Hello, friends. Happy Saturday! Today I’m posting a recap of my 25 Days of Winter Fashion in case you missed any of my looks, and so they’re all in one place for easy reference. Here they are, in no particular order, 25 winter outfits for women over 40!

(Feel free to pin this image to your fashion board on Pinterest so you can find it easily. I also put it on my blog sidebar with a link to this post.)

25 Winter Outfits for Women Over 40

While this one was challenging, I think this might be my favorite seasonal style collab yet. Fall fashion was fun, but it was so warm here this year, it was hard to get in the spirit of the challenge. I’ve enjoyed putting together winter outfits with the various layering possibilities, and I feel like I’m really honing my fashion sense and coming into my own personal style while still being willing to step outside of the box every once in a while.

As y’all know, I’m no stylist or fashion expert. I’m just figuring this out as I go and sharing it with you, and I appreciate all the encouragement and positive feedback as well as the occasional constructive criticism.

So let’s break it down. Click through the numbered links beneath the images to see the full details on each outfit.

Days 1-5

1 // 2 // 3 // 4 // 5

Days 6-10

// 7 // 8 // 9 // 10

Days 11-15

// 12 // 13 // 14 // 15

Days 16-20

16 // 17 // 18 // 19 // 20

Days 21-25

21 // 22 // 23 // 24 // 25

Which outfit is your favorite? I’d love to know. I really think Day 21 is my favorite. It’s everything I want my style to be — modern but classic, feminine meets edgy, figure-flattering without sacrificing modesty… does that about sum it up?

Speaking of defining your personal style, Cyndi and I have an ebook in the works on exactly that topic. We were hoping to have it finished by last summer. Ooops! We had to put it on the back burner with everything going on in both her life and mine this fall, but we hope to wrap it up and have it available within the next few months.

She might send a lynch mob to Philly now that I put it out there, but I figure, if we put it out there, we HAVE to finish it!

Thank you, once again, for all of your support and encouragement this year! After a full year of doing the fashion-blogging thing full-time, I’m really feeling more confident and at home with this niche, and I’m so grateful for each one of you for sticking around while I find myself. Haha!.

Be sure to visit Cyndi and see the winter outfit she’s styling today!

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24 thoughts on “25 Winter Outfits // Fashion Over 40

  1. My favorite was day 8, and I bought that top! I needed a classy, simple top to wear to my home Christmas party and I like to wear shirt sleeves and this was perfect! I also got the sweater (before it sold out) from day 6 in the reddish color and love it! Love your style and blog!

  2. They were all beautiful, but my favorite was Day 21, too. You looked stunning in that ensemble. Thanks for all of the inspiration!

  3. JoLynne, How are you feeling? So, when there is snow on the ground, doesn’t that mean the water park is ice! I’d be on the sidelines as well.
    Regarding your outfits, I really like day 7 because you showed how I can wear the same color top and jeans then add a pop of color with my shoes, and look great. I also really like day 25 because it is something I would wear. I actually tried to order the long sweater from Target yesterday, but the site kept telling me it’s not available in my area. I’m not sure why!
    I hope y’all have an awesome family get away!
    Finding your and @CyndiSpivey’s sites have definitely been a blessing in so many ways. I’m looking forward to sharing 2017 with everyone.
    God bless!

    1. Ginger, I am finally feeling somewhat human again. It was a doozie of a cold. The waterpark is all inside. 🙂 No ice. It was actually so warm I had to buy a t-shirt to wear b/c I was roasting in my turtleneck. Thanks so much for all of your comments and encouragement throughout the year! xoxo

      1. I understand about the cold. This Thursday will be the two week mark for me. I am finally going to see a nurse practitioner in town tomorrow afternoon because it has settled in my ears. Jo-Lynne, I so appreciate you taking the time to reply to our comments, especially when we have a question. I know that it is time consuming, and it doesn’t go unnoticed. You doing so helps us be better friends. I pray that you and your family have a very Blessed and Merry Christmas and Happy New Year!

  4. Thanks again for another great series! I think my favorite is Day 10, but #1 and #19 were favorites also. They’re all something I would feel myself in and could easily recreate. I’m still kicking myself for not get those scarves, but I had to keep reminding myself I have plenty to get me through the few days I could actually wear them! Ha! But really, thanks for all your hard work with these and the extra posts with gift ideas and such. You must be so relieved it’s over! 😉

    1. I love all of those outfits too! It is a bit of a relief to be done, but the outfit posts are my favorites to write, so it’s also a bit of a letdown. 🙂 I am happy to take a couple weeks off, but I’m looking forward to new outfits in January! Glad I’m not doing the capsule wardrobe again. Haha!

  5. I enjoy your blog and Cyndi’s so much! Quite often I can shop my closet and sort of duplicate one of your outfits with just the addition of a new accessory. Day 21 is my favorite. I’ve asked Santa for a grey scarf! Please keep doing what you are doing! Your blog is the perfect combination of helping us learn about fashion/style and sharing about your life. Feel like we are friends from afar! Wishing you a very Merry Christmas!

  6. Hi Jo-Lynne. On you my favorite is 21, as well. For me, I love day 25. In fact I’ve got a question. What are your thoughts on a sweater like that with a hood and a scarf? Many of my sweaters have hoods and I never know if I can wear a scarf. I usually end up wearing them and they don’t interfere, but I may start look for non hooded ones soon. Thanks!

  7. I love 21, but also like 20. It is not a look I could pull off but looks amazing on you & is sort of an edgy party look to me. Love your posts. Have purchased several items here & there from them & love them all! Have a grand weekend!

  8. I really like #18. I like #24 too. I also like many of the ones mentioned above. I have to remark on the pastels. It just is a soft beautiful look.

  9. #18 and #21 with a special smile for #19….your look AND the pup! Thanks for what you do….you and Cyndi are my favs!

  10. i agree – love #21. But I also love 18, 12, 13 and 9. Hard to pick a #1 when there are so many great options! Hope you are enjoying your Christmas-y weekend in the Poconos 🙂 Cheers!

  11. I am absolutely hopeless so in no particular order my favourites are: 12,13,16,18 and 19! The message from all that? What a great series Jo-Lynne! Thank you so much for your gorgeousness, good humour, grace and style.

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