Here are easy classic basics to uplift your casual Fall outfits for women over 50. They include a graphic tee, lug-soled loafers, ankle crop jeans, casual slip-on shoes, a chambray shirt, and a maxi skirt.
It’s time for our annual Fall Fashion edit with Cindy, Annie, and other stylish Over 50 women. Their links are at the end of the post!
You probably have some of these classic pieces in your closet already! At this point, I am more into mixing up what I have than buying a lot of new things. But it does help to inject one or two new articles of clothing to make everything feel fresh for Fall.

Easy Classic Basics List:
- Chambray Shirt
- Maxi Skirt
- Booties
- Graphic Tee-Shirt
- Loafers
- Ankle Crop Pants
- Slip-on Shoes Like Vans
There are some affiliate links that may generate a small commission for me at no extra cost to you.

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Chambray Shirt
The shirt that I’m wearing above is several years old from the Banana Republic. Gap Factory has a similar one for a great price right now.
Maxi Skirt
A few years ago, Cindy H. alerted me that she saw a CP Shades maxi skirt on EBay. Cindy finds great deals there. So I bought it. I’ve been wearing the one above ever since with different tops.
And this year maxi skirts are on a lot of “2022 Trends” lists. Here is a cute black maxi skirt from Anthropologie in petite, regular, and plus sizes. This one from Nordstrom is similar to the one above (although I would probably have to shorten it since I am 5’1″).
Booties
I bought these booties last week for half price at Nordstrom. They are waterproof and the block heel makes them more comfortable.

Graphic Tee-Shirt
My daughter’s friend, stylist Allison Bornstein mentioned on Instagram how a graphic tee-shirt can freshen up a suit or outfit. I saw some at the department stores for over $100. Then I thought of checking out Lucky Brand and they have lots of fun ones.

Lucky Brand has a deal where if you buy one you get 50% off the second, so naturally, I purchased two that spoke to me 🙂
Ankle Crop Pants
Someone called these “highwaters” but ankle crop pants have been a fashionable length for a while now.

How do you like the new golf cart? It’s got a nice sound system. We made a rule that we have to take turns driving (it’s so fun) and the driver gets to choose the playlist. Fewer arguments. 🙂
Loafers
These are comfortable loafers by Madewell…I will be wearing them often this Fall. They were 30% off with their Insiders Event. So, if you are on the fence (I was), now is a good time to buy them.

California Casual Slip-on Shoes Like Vans
Here I am at the LAX airport (flying back from visiting our new granddaughter) in another graphic tee (in a small–size up if you want more of a boyfriend look) and grey and black checked Van’s.

Fave Fall Accessory
CHIEF! He was so good at flying coast to coast. I did give him a little sedative from the vet (heck, I would want one if someone put me in a bag under the seat for that long). We took him since we were going for two weeks.

This is also relevant: Four Key Pieces To Update Your Fall Wardrobe.
Now, let’s check out what my friends have curated for us for Fall fashion…

Curious about the sock choice for loafers. I typically have higher or lower vamped shoes, so the loafer is a footwear option I’m interested in but I don’t know what to do about socks. I am not a fan of having a full sock showing in the loafer, but what do you choose for the no-show look? And then how do you keep them from slipping off your heels? Thanks!
Great outfits! Also love your sunglasses and readers. Can you share those brands?
Thanks!
I love all your outfits! I really like your lip color. Can you share your color?
Love all your outfits! Love your style.
Can you tell me what color lipstick you wear. I’m on a search 😊
Usually Nars American Woman…but sometimes I put another on top.
How do the Blondo booties fit? Nordstrom reviews seemed to veer towards a narrow toe and ‘slippy’ heel area. They’re super cute, though, and a great price!
Mine feel comfortable to in my regular size. They are easy to return if they don’t work for you. I wanted an alternative to the flat booties that I have.
Isn’t it wonderful how simply adding a couple of new pieces can freshen up a whole wardrobe! I am also a big fan of Vans!
Congratulations on your new grand daughter!
Thanks, Tamera! Loved learning more about you.
Great post: hope it is cooling down enough to wear crops already in northern FL…
Loved seeing Chief in travel mode! Our first dog, a mini poodle, traveled the world with us when we took family visits to Italy for 3-4 weeks and to CA for the holidays (our beloved Barba: “beard” in Italian bc she had so much facial fur when we got HER and in English, it sounded feminine!).
Re. loafers: just purchased lugged loafers with a white sole (that actually fit my difficult foot), and now all the soles are back to black — fashion!
What a lucky dog!!! I actually wore that cropped pant outfit to dinner the other night. But it still feels like summer here! Supposed to be in the high 70s next week.
You look adorable in every single outfit!
You are so nice, Kathy!
Great choices, Mary Ann! You’ve styled everything so well. And you pup is SO cute!!
I love YOUR pup, Susan. Great post!
You are so cute! I need to find a maxi skirt….but most of the ones I try on have too much fabric! I’ll keep looking cause Lord knows I need to be on trend:)
You are already effortlessly chic, Sherry!
You look amazing! You’ve really managed to effortlessly move from city chic to beach chic!! Love all your looks and those CP shade maxi skirts are amazing! So great for travel!
Thanks, Annie…LOVED your foreign correspondent travel post.
Happy you are living in Florida now! Love your style and nice seeing more clothing for our “warm” climate. Smart idea for the little bit of sedation for pup. It has to be better for Chief being in the terminals and airplanes!
Thanks, Candy. I’m hanging on to my jackets for the few cold days and for travel…but I definitely need to “curate” my SF wardrobe.
Chief refuses to use the Pet Relief areas at the airport. So in Houston (a BIG airport), I had to run him outside to the curb and then back through security. But he was good and I’d do it again.
AS always, love your post! How do the Madewell loafers fit? TTS?
True to size…I normally wear a 7 but a 7.5 if they are pointed. These are comfortable in a 7.
PS. Thanks, Sue!