Fall/Winter Fashion
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25 Fall Outfits for Women Over 40

Happy October, friends!!! Time just keeps marching on, doesn’t it? Today I’m recapping my 25 Days of Fall Fashion, a style series featuring 25 fall outfits for women over 40 including casual looks, date night ideas, and work wear for your style inspiration!

Jo-Lynne Shane styles 25 fall outfits for women over 40 including casual looks, date night ideas, and work wear for your style inspiration!

I really tried to show more variety in this series than what I wear on a typical basis — I tried some new silhouettes and showed some dresses, but I always get to the end of one of these series and wish I’d done better. There is a serious lack of skirts and casual pants in this set, but I literally never wear either so… I guess I did alright, considering.

My favorite looks are still the skinny jeans with sweaters (shocker!!!) but I’m warming up to the straight cropped jeans, and I always love a good bootcut outfit every once in a while.

Let’s break it down…

25 Days of Fall Outfits for Women Over 40

DAYS 1 — 5

We kicked off the series with dark wash bootcut jeans, a gorgeous purple shirttail hem sweater, and grey peep-toe booties. I’ve worn a few variations of this outfit since, and each piece has become a fall wardrobe staple this season.

I showed an athleisure look with ponte moto leggings and a striped pullover for day 2, and then I styled straight leg jeans on day 3. There was a lot of good feedback on that post with ideas on tweaking the outfit to make it better.

The next outfit was work wear and not my favorite, but the comments were really fun to read, and I think we all learned something. I came back strong on day 5 with the floral blouse with my black skinnies and a pair of fabulous mules — definitely one of my favorite outfits of the series.

one // two // three // four // five

DAYS 6 — 10

For day 6, I styled a lace trim cami at a reader’s request, and I paired it with this really fun paystub jacket. I wore bootcut jeans for variety’s sake, but I prefer the outfit with skinnies and wore it that way to have lunch in Philly a few days later. My day 7 outfit with the sleeveless cowl neck top and red mocs is one of my favorites of the series, and I’ve already worn it a lot in one variation or another.

I like the work wear look on day 8, but it could use some accessories and maybe a different shoe. I about melted in 90-degree heat to get photos of the cashmere sweater on day 9, but it was worth it. That outfit will definitely come in handy once the weather cools down. Then there are the infamous yellow pants on day 10. #winsomelosesome

six // seven // eight // nine // ten

DAYS 11 — 15

I styled a really pretty floral blouse on day 11, wearing it with my trusty 7FAM high waisted skinnies and peep toe booties — two of my favorite wardrobe staples this season. Then I partnered with Kohl’s on day 12 to talk about completer pieces, and this camo jacket was a reader favorite.

The sweatshirt trim sweater outfit on day 13 is another one of my favorites from the series, and one of the most true to my personal style. Also, that sweater is by far the most popular item of clothing I featured during this style series, according to my analytics.

I brought you a tweed shift dress on day 14, and then on day 15 I’m back in my comfort zone with a pullover sweater, skinny jeans, and leopard slides. I always say I don’t buy duplicates, but that rollneck sweater is worth making an exception for — I’m seriously crushing on the dark papaya.

eleven // twelve // thirteen // fourteen // fifteen

DAYS 16 — 20

Next I styled a really pretty lavender cardigan with grey jeans that a lot of you loved, and on day 17 I partnered with Nordstrom to style an outfit with straight cropped jeans and leopard booties. I think that might be my favorite outfit of the whole series, and FYI, those booties have been restocked!!!

I featured an open front poncho on day 18, and then I brought back the yellow pants on day 19. I think we all agree this look is much better than the one on day 10, but there’s still room for improvement.

Opinions were mixed on my camo pants, but I like the look for a change, and I really like that denim jacket I wore with them. It was a new purchase this fall, and it’s going to be a great year-round wardrobe staple.

sixteen // seventeen // eighteen // nineteen // twenty

DAYS 21 — 25

The stripe v-neck sweater I featured on day 21 is nice because it can be dressed up or down, but I went for a more casual look since I had some requests for more athleisure. I’m not a fan of wearing yoga pants or leggings when I’m out and about, but I like to wear black jeans and black leather slip-on sneakers with casual tops for a dressed-down but put together look.

I styled red booties on day 22, and while I love them with the bootcut jeans, I will definitely be sharing other ways to wear them this fall and winter. The twist-front sweatshirt on day 23 was the 2nd most clicked-on pieces of my entire outfit series (after the sweatshirt trim sweater) and with good reason. It’s such a great casual piece and comes in a bunch of fun colors — another top I’m tempted to buy two of.

The floral blouse on day 24 isn’t my favorite, but I tried to turn the post into an opportunity to explain the rule of thirds as it applies to outfits. Finally, I wrapped up the series with a pretty mosaic shirtdress and knee-high boots.

twenty one // twenty two // twenty three // twenty four // twenty five

photo credit: Alison Cornell

So that was fun! I hope you enjoyed these fall outfits for women over 40. I always enjoy hearing which looks were your favorites, so feel free to chime in, and be sure to visit Cyndi to see the her 25 Days of Fall Fashion recap today!

I’m also up for suggestions for future posts. It always takes me a few days to get my sea legs under me after a series like this. I get so used to posting outfits that I suddenly feel at a loss for other topics. I need to spend today planning my editorial calendar for October and prepping some posts because right now I have nothing in the queue except for a couple new fall outfits, but at least I have that!

Facebook Lives Resume Tuesdays at 1PM EST!

Yes, that’s right. I’m planning to bring back my Facebook Lives! We’re going to try for Tuesdays at 1PM and see how it goes. I might have to change the time, but for now I think 1PM is a good one to try for.

These Lives are just basically a time for us to chat — topics vary from open Q&A sessions to unboxings to seasonal style topics, but I don’t usually have much of a script. I like to leave it open ended so I can answer your questions, but I try to have a few things to talk about in case it’s slow.

It’s nice when I get some of your questions beforehand so I can prepare, and also to have some things to discuss while people are joining. I’ll try to remember to ask for those ahead of time, but you can always email me your questions throughout the week and put “Facebook Live” in the subject line. You can ask me anything — it doesn’t eve have to be fashion related, but that’s usually wear the conversation ends up.

Anyway, be sure to mark your calendars for Tuesdays at 1PM if you’d like to participate!

All you do is go to my Facebook Page (make sure it’s my blog page, not my personal profile) and it should show up once I go live. I try to be on time, but sometimes I get on a few minutes late, so refresh your screen if you don’t see it right at 1PM.

If you can’t attend at that time, I always save the Lives to my Facebook Page, and I try to remember to link them in my email newsletter each week. Even if you’re not on Facebook, I believe you can watch them on your computer from my link.

Speaking of my newsletter, the winner of the September giveaway did not claim her prize, so if you’re a newsletter subscriber, be sure to check Saturday’s newsletter and see if it’s YOU!!! The winner has until midnight tonight to email me back, or I will choose another name.

If you don’t subscribe, you can SIGN UP HERE and be eligible to win a $50 gift card each month! Plus you’ll receive a notification of my latest blog post AND exclusive newsletter content like special sales, my newest favorite finds, and a peek behind the scenes — all delivered right to your inbox. You can choose a daily or weekly option, and the weekly newsletter comes out on Saturdays. (I always announce the giveaway winner in the newsletter on the last Saturday of the month.)

So that’s about it! The sun is shining here in Philly today and the temperatures are moderate… it’s basically the perfect October day. Plus my calendar is blank, which is such a great feeling. I’m looking forward to spending the day puttering around the house and working on future content for the blog. I hope you all have an absolutely marvelous Monday!!!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

Join the Conversation

46 thoughts on “25 Fall Outfits for Women Over 40

  1. Thanks for the recap!!  My winter “uniform” is also skinny jeans and a sweater but I’m trying to “expand my horizons”. A suggestion for a topic— jumpsuits. My 25 year old daughter has several casual ones and they are adorable. I’d love to try one but have hesitated, worrying I’ll just look silly. Decided to start with a dressy one. I have a wedding to attend that is dressy but not so dressy that I would feel uncomfortable not wearing a dress. Struggling to find the right one though. And most are black. Have you tried jumpsuits, Jo-Lynne?

    1. HEY GIRL!!! I was thinking about you just yesterday and thinking it had been a while since I heard from you. I have tried jumpsuits, and they all look AWFUL on me. My biggest issue is I’m so short waisted. This one is the best one I found, but of course old and sold out: https://jolynneshane.com/jumpsuit-style-collab.html

      I’ll keep trying tho. In fact, I thought I just ordered one but I never got it in the mail. I’ll have to check my emails.

      1. I never miss a post. Just been super busy— vacation, children and grandchildren, and caring for my dad. I moved too, and of course there’s the day job. 

        Thanks for all the work you put in each day to connect w/ your readers. 

  2. Thanks for a great fall series. Nice to have the recap to refer back to. Would like to see a few athleisure wear outfits for home but changed up to wear out. Also if you’re  wearing a dress with a taupe bootie and don’t want bare legs or pantyhose what would you suggest ? A neutral tight? Enjoy your sunny day it’s a beautiful fall day here too.

    1. Also I had a crew neck tee on one day with a cardigan and it didn’t feel right so I bought a v neck which felt better; However with my denim jacket I like a crew neck.. is there a rule of thumb here? Also I’m small busted. 

    2. The taupe booties with dresses are tough. I will have to research that one! I’ll write it down for the FB live tomorrow. 🙂

      I honestly don’t really wear athleisure even at home… I guess I have one or two pairs of joggers (ironically, wearing them now with a tee and cardigan) but I would just swap them out for jeans if I were going anywhere. I don’t wear leggings except with tunics, and that is rare. I dunno, I guess the athleisure trend has never really done it for me, lol! If I want to be comfy at home, I usually wear my oldest ripped AG legging jeans and a tee or sweater. Those jeans feel as comfortable as any leggings I’ve worn. Still, that could be a fun challenge for a blog post!

  3. Could you do a review on ballet flats? I have been trying to find an affordable comfortable pair, and I don’t think I am ever going to find them. I really enjoy your blog, I have learned a lot about fashion and being in my 40’s.

  4. Hi Jo-Lynne!
    Thanks for another great series! I would love to see a post about selections for a trip using items from your fall series……maybe for a 3-4 day or long weekend that would include just the kinds of things you just described……family time, football game, casual church. It would be nice to be able to pack a few of these items with similar jewelry and shoes and be ready to go. You always are lovely and so put together- look forward to your blog every day! 

    1. It should come to your email every day. I looked at your MailChimp profile and it says you’re getting them. If you’re missing some, check your spam. Gmail can be really cranky sometimes. Also check your Promotions folder. Or better yet, search my email — [email protected] .

      1. I don’t get a newsletter either. Is it separate from the normal email? I tried to sign up again, it said to click on the link in the email sent to me, but there was no email. Hmmm

  5. So funny that the sweatshirt-trim sweater and twist front sweatshirt were both so popular. The ones I had to refrain from buying myself were the floral blouse you paired with black skinnies on day 5 and the navy wrap top with blue skinnies on day 11, as well as that last dress on day 25. I suspect I might be on the dressier end of your readership as far as my lifestyle demands, not that casual is a bad thing. I wish I could wear sweatshirts more often! Have a great day!

  6. I am not buying anything fall/winter til it gets at least 70 during the day so that may be Nov. But I do enjoy your blog to see what is trending and see if anything I have fits that. And it does. I think I am more into straight leg or boot at the moment for jeans. Maybe more fitted tops. Love all that you show us.

  7. Like I said to Cyndi – THANKS for putting all of this together for us!! I love the orange cardigan and sweater looks, but I also love orange for fall, so maybe that is why! I wanted to say thanks also for trying different looks for us, I know it isn’t always easy!

  8. Thanks for the great Fall series!  Lots of great outfits!  I’m such a skinny jeans and sweater person, too, but it’s great to be inspired by some options for shaking things up.  Looking forward to FB Live again!

  9. So many great outfits! I appreciate the challenge of changing your look up for 25 days. We all have our “ uniform” in some way and tend to stick to variations of that. If I had to pick my favourite it would be #1 . You look long and leggy in bootcuts. The whole outfit flowed. But there were lots of winners!
    I’m into bootcuts at the moment. Having gained a few pounds ( up a size) I feel I look slimmer in them. But, come winter I’ll be back into skinnies to wear with my boots. I feel with boots it balances the look. 
    Can you do a post on what’s in and what’s considered old news in footwear – heel style, shaft height of booties, etc? I read open toe booties and wedge heels are out. Truth? 

      1. I’m not on Facebook, Twitter, etc. I am on Instagram and even that I rarely post to, but do look at others’ pretty pictures. My iPhone remains in my purse unless I get a call or have to make one. All these forums become time thiefs. I spend enough time on blogs and feel a little guilty about that. I’ve deleted all but my favourites. Yours is the first one I read every morning. 
        Have a wonderful first day of October! 

  10. Day 7 was my very favorite. Love the cowl the jeans and those red mocs. I purchased them in both the chestnut and the black ( could kick myself for not getting the red, thought that would be terribly redundant). Such a cute casual pulled together outfit. As far as future posts…please do one on pumps. I need a pair of black pumps and just can’t find a decent pair. Maybe with different ways of styling. Love your posts and looking forward to your live(I look forward to watching after school). It is so beautiful out(in Princeton NJ). Thank you for your post.

  11. I always love seeing all the outfits you styled in a collage. Thanks again for the fashion inspiration. Some ideas to explore could be fall jackets, then winter jackets for those of us who have to endure cold temperatures. I would love to have help with what to wear to Thanksgiving early so I have time to order, get the item altered etc. It seems many families have casual get togethers on Thanksgiving. Maybe take your outfit and expand on how someone who has a warmer skin tone might select a different color or what someone with a different body type might choose a different style. I loved it when your daughter styled some clothes,. In fact I took my granddaughter shopping and we bought the entire outfit. Any trends for guys this fall? 
    As always, thank you for inspiring me to dress better and for being so open about your life. You truly are the girlfriend next door. 

  12. Great recap. Here are a few ideas: Would love to know what your favorite running socks are. Whether all of the varying jeans you style fit right in your hip area…I can try on 25 jeans, but only one fits right. Do all of these different brands/styles really feel good? What do you wear as an under layer under sweaters? It is too cold in the Midwest during the winter to not wear a tank or cami underneath…..searching for a new favorite. Favorite makeup/beauty products. Everyday life tidbits! Keep up the great work!

  13. I really like skinny jeans with sweaters or tees so naturally those were my favourite outfits. Thanks for a great fall series. I would love to see how you decorated your house for fall. That kind of post is a favourite because I LOVE fall!

    1. I haven’t done much, but I’ll try to snap a few pictures of what I’ve done. I’m still working on the foundation of my decor so I haven’t been able to really focus on the seasonal. Next year, maybe!

  14. Hi Jo-Lynne! I always love your recap posts- there’s just SO many good outfits for inspiration! I am wondering if you switch up any of your makeup for fall? Do you have favorite fall nail and lip colors that you go back to, or any new ones you’ve discovered? I’m a cool undertone as well. I am interested in holiday looks- I know it’s a little early for some people, but the weeks fly by and then all of a sudden I need holiday wear! I do not wear dresses, and am wondering if you could feature blouses, cashmere sweaters and jewelry or accessories and how to ‘level them up’ to church, office party appropriate, Date night, girls night, etc. I am also wondering what is ‘in’ with jewelry this fall and winter- are statement necklaces out? Sorry for all the questions, lol. I follow you, One Little Momma, Cindy Spivey, Adore Your Wardrobe(member), and Hi Sugarplum for all my fashion and beauty advice. Thanks! 

  15. I love seeing all the outfits again in the end and hearing your thoughts on which ones worked and which didn’t. I appreciate your willingness to step out of your comfort zone!! I’m going to second the comment about packing for a trip based on some of these outfits…that seems like a fun idea. Also, I really love the wear multiple ways types of posts. I’ve learned so much from your blog but i have to always restrain myself from buying something new every other day! 🙂 Need to be a good steward of my closet and just use your ideas as inspiration – you know?

    1. Absolutely, and that is what I hope everyone will do. Styles turnover so quickly in stores that I have to constantly feature new things so I can link to them, but no one buys a new wardrobe every season (except fashion bloggers, haha!) and I wouldn’t want anyone to think I’m pushing people to buy new stuff all the time. I’m definitely planning some more 3 ways posts and other types of content that helps rework the clothes we already have. 🙂

  16. There were so many great ones, too hard to pick a favorite! I’m beyond ready to be able to try some of these looks. Texas just needs to cool down already. Sigh.
    I had to let you know, though, I just got the UGG mocs in last week and I’m obsessed. I honestly didn’t care for them at first, but the more I saw and heard about them, the more they grew on me. They were such an amazing buy for 60% off!

  17. Thanks for all the inspiration! I love florals so I’m happy you mixed in a few. I liked the crop straight leg jean on you. Planning to try them soon but like you they’ll never replace my skinnies!

  18. Fantastic fall series. I didn’t get a chance to comment much but I enjoyed the variety of outfits you posted. Day 3 was my absolute favorite followed by the Day 2 athleisure outfit, the tweed dress and the shirtdress (both bought!)

  19. I got the Leith Cardigan and the Ugg Loafers for my birthday! I cannot wait to wear them! Its raining here in MI so not today.

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