I updated this post in February 2017. Many of these Fall looks make great Winter to Spring transition outfits. Affiliate links to similar pieces have been added. Many of these pieces are at end-of-season sale prices!
Oh how I love my Fashion Blogger friends! These are real gals, living on real budgets, with the bodies of real midlife women. They travel, they work, they play with their kids and grandkids. Their clothes have to be versatile and they are more likely to pick up a few key pieces each season to work with what they already have than go out and buy a whole new wardrobe. So check out these Fun Fall Looks From My Favorite Fashion Bloggers!
[bctt tweet=”Winter to Spring transition looks from my favorite fashion bloggers!” username=”MySideof50″]
This post contains some affiliate links for your convenience. Click here to read my full disclosure policy.
Shelly Janac – The Queen In Between
Shelly is my girl. She lives in Southeast Texas not far from me and totally feels my pain when it is pushing 100 degrees in late September. But heat and humidity be damned – Shelly finds a way to keep cool and dress for fall at the same time.

Shelly wearing a sleeveless swing top in Buffalo check & white skinny jeans. The sleeveless top in a Fall fabric is perfect for hot fall days in Texas.
Buffalo Check sleeveless dress worn as a tunic over white skinny jeans with leopard clutch and booties. Red & black check says fall. Sleeveless says “Fall in Texas”. Love this look.
Shop the Look: Handbag (similar here) White Jeans (similar here and here) Black Booties (similar here)

Shelly paired her floral top and white skinny jeans with a mustard colored light weight cardigan. The fall color of the cardigan takes these summer staples right into fall.
Here she wears those same white skinnies with a floral top. She adds a mustard color cardigan for a touch of fall color and her Texas Aggies spirit is showing through in those cute maroon colored booties.
Shop the Look: Floral Shell (similar here)
Shellie Bowdoin – The FABulous Journey
“When it comes to Fall fashion, the chambray button-down shirt is my must-have transition piece. I love the chambray shirt for a host of reasons. For one, it adds a polished, yet effortless vibe to any outfit. It can easily be dressed up or dressed down for any occasion.”
Shop the Look: Chambray Shirt (similar here) Turquoise Sandals (similar here)
“Also, the chambray shirt is great for layering, which is a necessity when the temperature just can’t quite decide what it wants to do throughout a given day. You can wear a chambray shirt in the traditional way, whether tucked in or out. Or, you can use it as a jacket or knotted over another shirt…the possibilities are endless. Just remember that a chambray shirt is a neutral, so it can be mixed and matched with almost any color palette.”
Shop the Look: Black Sandals (similar here)
[bctt tweet=”A chambray shirt is a neutral and can be mixed with almost any color pallette. @ShellieBowdoin” username=”MySideof50″]
Check out this post: Chambray Shirt as a Jacket by Jodie’s Touch of Style
Susan Street – SusanAfter60
I have followed Susan on Facebook and Instagram for quite a while. She is so lovely and chic. But if you follow her closely, you’ll see she doesn’t wear a LOT of different clothes. She has a basic color palette – white, black & denim that she has learned to style so many different ways, you’d think she had 10 closets full of clothes.
Here is Susan in a basic, black tank dress and white blazer. She says:

Susan’s versatile black tank dress can be worn with a jacket or sweater, boots & tights or sandals & a straw hat.
Shop the Look: Dress (similar here) White Blazer (similar here) Taupe Heels (similar here)
“I am wearing a dress that can be worn with almost any jacket or sweater. It can be worn with boots and tights or sandals and a straw hat. Owning pieces that travel well and are versatile are much more important to me now. I am going on more fun getaways than ever before, but I don’t want to be burdened with a lot of luggage.”

Susan adds color to her black wardrobe staples with the colorful tank and scarf tied near her portrait area.
In this picture, Susan’s core pieces are black pants and a black duster. The blue top and printed scarf add color and texture near her face. As we age, we lose color, so having colorful pieces near our faces can brighten our whole look. Also, as another fashion blogger friend, Jennifer Connolly once told me “texture NEAR our face minimizes the texture ON our face” – if you catch my drift!
Shop the Look: Black Ankle Pant (similar here) Black Duster (similar here) Black Shoes (similar here)
[bctt tweet=”As we age, we lose color, so having color near our face can brighten our whole look.” username=”MySideof50″]
Susan offers these tips for scarf tying:
- Tying a scarf near our “portrait area” avoids adding more bulk at the bust.
- If I am wearing a larger scarf with more texture for warmth, I will tie or wrap it so that it hangs in smooth straight lines rather than adding more fluff where I am already “fluffy”.
[bctt tweet=”Tying a scarf near our portrait area avoids adding more bulk at the bust.” username=”MySideof50″]
Glenda K. Harrison – So What to Twenty
Glenda is my fashionable friend who is bold, confident and fashion forward in her look. She inspires me to step out of my comfort zone and think about who I am and what I am portraying when I get dressed to meet the world every day!
Shop the Look: Jeans (similar here and here) Black Booties (similar here)
This fall I plan on introducing my closet to a variety of unique outerwear options. In this day and age, the traditional suit jacket or cardigan have been upgraded to include more interesting details and flair. I plan on creating a juxtaposition of high/low and have them come together to weave a clever take on downtown cool:
- Structured shoulder tuxedo jackets paired with deconstructed denim.
- Cardigans with bell sleeves or creative interest with flutter backs paired with a classic equestrian look.
- Combining a baroque-inspired floral bomber jacket with unexpected pieces like a metallic skirt, velvet jeans or classic denim.
Since I enjoy adding interesting elements to my wardrobe, these tricked-out, classic, outwear choices will give me just what I need.
Shop the Look: Black Skirt (similar here) Black Sandals (similar here)
Since personally witnessing the Monique Lhuillier runway show for fall 2016, I fell more deeply in love with the idea of wearing ankle socks with open-toe sandals or traditional heels, since many of her catwalk looks showed the models wearing sequined socks with her beautifully fabricated garments. Granted I know this look isn’t for everyone, but it is a quirky and adventurous way to express your more creative side. To pull this look off without a hitch, I strongly suggest:
A) You have the personality to wear it with confidence.
B) You select ankle socks that compliment your look with subtle color variations.
C) Make sure your socks do not have re-enforced toe and heel in a different color. Meaning, if your sock is white with black polka-dots, you do not want the toe and heel to be black.
What do you think? Did you get some new ideas to try? New combinations from your own closet? If you like this post, please share it. Pin it on Pinterest or Share it on Facebook.
You might also like:
Outfit Ideas: What to Wear Shopping
Quintessential Style: Cultivate and Communicate Your Signature Look
Get Your Midlife Style Back: How I Did It!
Accessories – The Icing on the Cake
Lessons Learned From My Favorite Fashion Bloggers
Tie A Scarf 3 Ways!

Like to accessorize with scarves, but bored with the way you are tying them? Subscribe to My Side of 50 and get 3 Fashionable Ways to Tie a Scarf TODAY!
Beautiful women modeling beautiful clothing! Love this post!
I love all of these ladies—it’s so refreshing to have women our age showing that style doesn’t have to leave us as we get older!!!
Thanks for including me in this great post!!
jodie
http://www.jtouchofstyle.com
Cathy, how clever of you to create your own fashion week. I love it! Thank you for including me with such fashionable women.
Where did Glenda Jackson get that jacket? Love it.
Hi Susan! I’m Glenda Harrison. Here is the link to the post. I have the location of the jacket listed. Happy Shopping!
it’s lovely to see all these fabulous ladies here. I really enjoyed this post .
http://www.vanityandmestyle.com
I love these looks. It just needs to cool down a little bit so I can copy some of these looks.
Debra, I hear you! I live in Texas and am still wearing shorts! Thanks for reading and commenting!
What a great post! I am 66, and I love seeing the fashionable ladies in your photos. Kudos to you! We are NOT invisible!
Amen – gorgeous group of ladies. They are inspiring. Thanks for reading and commenting, Mimi!
[…] Fun Fall Looks from My Favorite Fashion Bloggers […]
Cathy we have got to have a meet up some day…just too close not to!! Your sweet words just made me smile so big this morning! Oh how I only hope I can look as beautiful in my 60’s as Susan. wow!!
Isn’t she just gorgeous! Thanks so much for being a part of the post again. Everyone LOVES your looks! Next time I drive to Austin to see my daughter, maybe I can run by CS and we can grab a cup of coffee. Or if you come, this way, let me know. Would love to meet you in person!
Love the soft layered look, it’s so important when it’s chilly in the morning and evening, but so warm during the day. Super classy looks and so beautifully confident too, just they way we should be 😉
Michelle – so glad you liked the looks! I love all of them!
Fabulous looks! Gorgeous bloggers! Love the chambray shirt! And I love how they’ve made it easy to mix and match. Thank you for a delightful post, Cathy!
So glad you liked it Vidya. I’ve ordered a Chambray Shirt – such a great year round piece!
Cute outfits! I really loved the Chambray Shirt layered with an orange tunic.
Wasn’t that cute! I never would have thought to put that together. I just ordered a Chambray shirt from Talbots!
Some great looks here. It’s still so hot where I live, I am loving all the open-toe shoes.
I feel ya! I’m in Texas and it’s still shorts weather here. Glad you liked the looks!
Love it! Guess who needs to go shopping!
I know – aren’t they inspiring?
Thanks for all the great ideas! I never know what to wear this time of year. In NJ it’s already in the 50’s and I haven’t changed my closets around. These ladies look fabulous! (I wish I could still wear heels. It’s flats all the way…) Great post!
So glad you liked the looks, Cathy! Thanks for reading and commenting!
Wow! I want to be Susan when I am 60!!! It’s actually still warm in NE Oklahoma also. Love the white pants and red plaid top. Updates the pants for fall, but not dying in the heat.
Laura – we all want to be Susan! I’m in Texas and it’s still hot here too. Shelly – who wore the white pants and red plaid shirt is also a Texas girl. We know what it’s like to be in the 90’s in September!
Thanks for introducing me to Shelly Janac. As another Texas girl, I feel the burn! xoxo, Brenda
Brenda, Shelly is awesome. Great sense of fashion. She lives in College Station and works for A & M.
Fabulous fall looks! Everyone looks fantastic! Great post!
I thought so too, Andrea!
such gorgeous women – each owning their own age and their own style – such great role models compared to the skinny little high fashion ones we have paraded under our noses by the media.
Good point, Leanne. They are great role models. Beautiful in every way.
What a way to begin my first morning in Santa Fe! I love all the bloggers and their picks. Shelley’s color combo rocks my world and Glenda is always fashion forward. But I got ideas from each of the bloggers. Lovely.
So glad you liked all the looks, Carol. These ladies are lovely and I get so many great ideas from them.
How fun are these outfits and bloggers! So different in their style choices, but fun and put together. I think I am a mix of all of them. I like to wear jeans and can see the tops and sweaters or jackets working for me. And I think I need to get some buffalo checks into my wardrobe and some booties! Thanks for the great suggestions to help me shake it up a bit this seson!
I learn something from each and everyone one of them. They inspire me to “mix it up” a bit with what I already have!
So much fun and such great ideas. Confidence is the best accessory! Loved the post!
I agree, Tammy! Confidence makes all the difference. So glad you liked the post.
Love all of these ladies rocking midlife and style. Great series Cathy.
Thanks, Sue! I love their looks.
[…] Fun Fall Looks From My Favorite Fashion Bloggers […]
I am so happy to see the white pants for fall! I love all the looks but I definitely don’t have the confidence to wear socks with my sandals. I wish I did because my feet are always so cold!
I just bought a pair of winter white jeans for the fall.
Lovely! I have been taking much more care with my clothes lately, Chicos has been giving me style!
I love Chicos! Great fit & quality!
I am a confirmed wear what I want kinda person, and it is nice to see women discovering and sharing their own confidence through clothing and attitude.
And they absolutely do – each with their own style.
I just found 3 new fashion bloggers who are great! (Two named Shelley…what a coincidence!) I was already aware of Susan, she is so elegant.
Susan is just gorgeous. And the other 3 are favorites. Glad you found some new ones to follow.
It’s nice to see fashion bloggers for the mature ladies. So really great looks.
I love all of them. They have so many great ideas to keep us looking stylish, no matter what our age.
Wow, I love all the fashion Ideas and I will be taking some tips from them. It is great to see ladies comfortable i their own skin
Julie – I agree. They are lovely!
Great trends and fashion! i found a couple of new bloggers to check out!
#PitStop
Great – all of these bloggers are great to follow. I’m glad you liked their looks!
Visiting from the Blogger’s Pit stop! – found a few new blogs to follow too!! thanks for sharing the post!
Helen – thanks for reading and commenting!
Cute outfit ideas. I will have to show my Mom as well!
Amanda – so glad you liked them. These ladies are fabulous!
My favorite is the chambray top… so versatile and cute ❤️
I agree – and Shellie styled it so well – in a way I never would have thought of!
Cathy, this post was among the most clicked on the Bloggers Pit Stop. Be looking for a feature on Friday. Well done.
So honored to be featured. Thanks, Kathleen!
[…] Fun Fall Looks From My Favorite Fashion Bloggers by Cathy […]
[…] Fun Fall Looks From My Favorite Fashion Bloggers by Cathy […]
Lovely friends and fashion choices. I like the ankle socks. I wear them but I know many our age think they’re juvenile. I think Glenda rocks the style and she definitely has the personality to pull it off. (and I don’t know her in real life) ^_^
Thanks for the tip about the scarf. I rarely use them as my round and chubby face doesn’t need any more attention. ^_^
Sara – yes – Glenda really pulls off that sock look. She doesn’t care what people think. She dresses in the way she wants to and looks fabulous. I like studying the different looks and finding what works for me.
One of the biggest mistakes we make with our clothing, is to think “I can’t wear that!” These ladies show that yes, yes indeed you can wear that! Love the looks and the colors on all these ladies.
Thanks, Olivia! All of those ladies inspire me!
Cathy, I am so honored to be included in your little style posse!! It is great to see what everyone picked. I have also enjoyed seeing you rocking your style picks on some other posts.
Shellie
Thanks, Shellie! I love featuring you in these posts! I have learned so much from you!
[…] Fun Fall Looks from My Favorite Fashion Bloggers […]
[…] Fun Fall Looks from My Favorite Fashion Bloggers […]
[…] Fun Fall Looks from My Favorite Fashion Bloggers […]
[…] Bowdoin, the blogger behind The FABulous Journey. Shellie has been featured in several of my fashion posts. By looking at her, you would never imagine that she has struggled with her weight. I didn’t […]
[…] To Twenty, has been a blogging friend of mine for the last year. I have featured her in some of my fashion posts and she has even done a guest post on my blog, My Side of 50. I admire her greatly, not only for […]