26 Wearable Fall Outfits for Women Over 40

Good morning, and happy October!!! It’s hard to believe that Cyndi and I are wrapping up our 5th seasonal style challenge. Today I’m posting a recap of my 26 Days of Fall 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, 26 fall 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.)

26 Wearable Fall Outfits for Women Over 40: Style for Real Life

1 // 2 // 3 // 4
5 // 6
7 // 8 // 9 // 10
11 // 12 // 13 // 14
15 // 16 // 17 // 18
19 // 20 // 21 // 22
23 // 24 // 25 // 26

So that was fun!! I really wanted to stretch myself this time and try some new things. It’s easy to revert back to my safety zone, which is skinny jeans and a cute top, but I’ll keep trying to expand my fashion horizons.

I always feel a little bit sad when one of these seasonal style challenges wraps up, but I have lots of ideas for posts, plus more fall outfits I want to style.

I have a couple of new dresses that arrived while I was gone, and one isn’t even a sheath. Shocker!!! I also want to do more with bootcut jeans and flares, and I have another blazer I want to feature if I can figure out what to wear with it.

I’ve almost given up on finding dress pants I like that aren’t jeans, but I’m determined to make it happen. I really need a classic pair of black or grey pants I can wear when jeans aren’t appropriate, but everything I try on looks frumpy. I need to make that a priority.

I’m working on a massive Instagram Roundup for next week, and I also want to share about my trip to South Carolina. Behind the scenes, I need to catch up on my Adore Your Wardrobe eCourse as well as my bookkeeping. Ugh. I hate bookkeeping.

Ooooh, unrelated to fashion, but if you’re on Instagram, I’m hosting a Starbucks giveaway with 7 other bloggers! It’s $100 Starbucks Gift Card for you and another $100 GC for the friend you tag! Super fun, and there are only 8 of us participating, so it’s not a ton of liking and following. ENTER HERE.

Starbucks Giveaway

Well, that’s about all I’ve got today! I hope you have some fun plans for the weekend. It’s been dank and cold and rainy here for the past few days, so I’m crossing my fingers that it dries out soon so I can enjoy some pretty fall weather. Right now I just feel like hibernating.

Our high school is hosting our annual cavalcade of bands tonight, so we will definitely be attending that, rain or shine. (My son plays drums in the high school marching band.) Other than that, I don’t have a lot on my agenda for the weekend. It will be nice to have time to get caught up on work and laundry… such a glamorous life I lead! Ha!

Make sure to come back on Monday for a huge Instagram Roundup of all the looks I’ve been wearing “in real life” over the past month. Or better yet, sign up for my Daily Emails, and you’ll never miss a thing. You can also follow along on Instagram for my daily outfits and sneak peeks of what’s to come on the blog, and register with LIKEtoKNOW.it so you can shop my outfits first! 

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26 Responses

  1. Thanks for another great seasonal series! Looking at all the outfits laid out, I find myself drawn to the more casual, but polished looks. My top 5 would be #1, 11, 14, 17 and 23. Great inspiration!

  2. Really enjoyed your fall series! Already “copied” a few of the styles & color combinations. I’m heading to a baby shower today, and it’s still cool, damp & drizzley. The cranberry top & black bottoms are an outfit I copied & I’m leaning towards wearing today. There will be a much younger group of gals there, so I’ll be casual, but not regular jeans casual, if you know what I mean! Thanks for all your inspiration & enjoy your downtime. The last few nights here in Pocono Region of Northeast Pa have felt like soup for supper, and snuggle down with an afghan kinda night! Oh, and the fireplace! Can’t believe we’ve had to fire it up already!

    1. So glad you’ve enjoyed it! I wanted to turn the fire on so badly last night. It was definitely that kind of night. My husband has to “turn it on” again and he wasn’t home. Maybe tonight!

  3. Love your blog. But I have a suggestion that you show some jeans that a woman with thin legs can wear. I’m sure there’s someone like me, thin legs and all, that need help. Thank you

  4. Thanks for a fun fall series! I found a pair of dressier black pants at Loft. The skinny ankle pant has a nice fit and I like the stretchy material, but more substantial than leggings and not as thin as their trousers. Looking forward to the flare jeans and bootcut jeans posts.

      1. Yes! Those are it. I bought them in store in black and they also had them in navy and grey at my store in Texas. For sure get ’em on sale!

  5. Hi JoLynne,
    Since we are talking about fall, here’s a question for you. What are your son’s high school colors? What do you wear to the band events and games? I am always trying to wear the school colors but hate the “band mom” frumpy look that I see all too often. Plus, I need to keep warm!!!

    1. Kathy V – I don’t like looking too frumpy either in school colors/clothes.. Have you ever bought earrings from Nickel & Suede? Check this out – they sell them in colors that easily match with school colors… https://www.nickelandsuede.com/shop/game-day/ It’s brilliant! As far as I’m concerned, if my earrings have school spirit, then I’m good to go. 🙂

  6. JoLynne, thanks for the recap. I don’t always get around to viewing all of your posts, so I like to see everything that you did for a particular series. You have some great looks and kudos to you for styling in some dresses. I’m not a real “dress” girl either, but it doesn’t hurt us to change it up a bit, does it? Love your looks. – Amy

  7. JoLynne, regarding nicer pants that aren’t jeans.. Are you into cords at all? Loft has some really great ones – Modern Skinny Corduroy Pants (they come in regular & curvy). I’ve bought two pairs and they are perfection. They are soft & fit like a glove & obviously can be dressed up a bit more than jeans.

  8. You are looking amazing this fall. Really slim and sassy!! How are your ankles? Knees? Feet? I can’t remember which! But I remember you were struggling with your health for awhile a year or so ago. Hope you feeling 110% cause you sure look it!

    1. Awww, thanks, Leslie! I am feeling very good. My ankles and knees and feet and everything are doing pretty well! It was a loooong struggle and for a while I thought I’d never be “normal” again. I was actually thinking about that as I was walking all over South Carolina in flat sandals – how I couldn’t have done that 3 years ago or 2 years ago or even last year very well. It was a long road to recovery with a lot of hiccups along the way, but everything seems pretty good right now. Just praying it stays that way!

  9. Hi Jo-Lynne…I noticed you are not wearing distressed jeans except the black pair…I am wondering what your thought are on the jeans with some light to medium distressing for our age group….thanks!

    1. Hi Georgia. The grey pair is distressed too. 🙂 I do enjoy some mild to moderate distressing, but I’m not a fan of big gaping holes. I say it’s a personal decision. I know some women do not appreciate the distressed look, but I think it’s more about personal style than it is about age, although age should play into the equation. Being over 40 with a fairly classic style aesthetic, I try to go for distressed styles that aren’t as extreme as what I might have worn 10 years ago. I hope that helps!

  10. Great roundup and great ideas! I work in a school so I can’t dress as nicely as I’d like most days, but you make it very easy to copy your outfits… even on a more casual (or sometimes cheap alternative) basis that works in my life. It’s pretty easy to throw on a $10 tshirt, jeans & a hoodie most days (and acceptable too) but it’s fun to add a few accessories or colored jeans 🙂 to make it a little more fun. Your posts show me so many “I could do that” ideas that I don’t see from other fashion bloggers.

    My daughter is in color guard so I know the fun of being a band mom and seeing the great things are kiddos get to do! Congrats to your son.

  11. Love your blog. Check out Chicos Reese cut pants. they are a fantastic chino fabric. Slim fitting but so stretchy you feel like you are wearing leggings. But these are what you are looking for as far as a nicer pant. Not too dressy and NOT jeans

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