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Easy Classic Basics To Uplift Your Casual Fall Outfits

September 22, 2022 By Mary Ann Pickett 24 Comments

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.

Mary Ann Pickett in Chambray shirt and maxi skirt with tan booties

You may also like Wallpaper In A Small Foyer Makes A Statement.

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.

suede bootie

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.

Mary Ann in a casual Fall outfit with denim jacket

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.

Chief in dog carryier

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…

Fall over 50 fashion

MOST LOVELY THINGS

CINDY HATTERSLEY DESIGN

TAMERA BEARDSLEY

UNE FEMME D’UN CERTAIN AGE

SHERRY HART DESIGNS

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Filed Under: casual, Style Over 50

Reader Interactions

Comments

  1. deborah says

    September 30, 2022 at 11:00 am

    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!

    Reply
  2. Lori Tally says

    September 25, 2022 at 11:19 am

    Great outfits! Also love your sunglasses and readers. Can you share those brands?
    Thanks!

    Reply
  3. Jean says

    September 24, 2022 at 4:20 pm

    I love all your outfits! I really like your lip color. Can you share your color?

    Reply
  4. Jeanie says

    September 24, 2022 at 4:17 pm

    Love all your outfits! Love your style.
    Can you tell me what color lipstick you wear. I’m on a search 😊

    Reply
    • Mary Ann Pickett says

      September 25, 2022 at 8:17 am

      Usually Nars American Woman…but sometimes I put another on top.

      Reply
  5. Tess says

    September 22, 2022 at 9:53 pm

    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!

    Reply
    • Mary Ann Pickett says

      September 23, 2022 at 2:01 am

      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.

      Reply
  6. Tamera Beardsley says

    September 22, 2022 at 5:18 pm

    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!

    Reply
    • Mary Ann Pickett says

      September 23, 2022 at 8:53 am

      Thanks, Tamera! Loved learning more about you.

      Reply
  7. Joan says

    September 22, 2022 at 5:17 pm

    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!

    Reply
    • Mary Ann Pickett says

      September 23, 2022 at 2:03 am

      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.

      Reply
  8. Kathysue says

    September 22, 2022 at 10:56 am

    You look adorable in every single outfit!

    Reply
    • Mary Ann Pickett says

      September 23, 2022 at 2:04 am

      You are so nice, Kathy!

      Reply
  9. Susan B. says

    September 22, 2022 at 10:54 am

    Great choices, Mary Ann! You’ve styled everything so well. And you pup is SO cute!!

    Reply
    • Mary Ann Pickett says

      September 22, 2022 at 11:12 am

      I love YOUR pup, Susan. Great post!

      Reply
  10. Sherry Hart says

    September 22, 2022 at 10:32 am

    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:)

    Reply
    • Mary Ann Pickett says

      September 22, 2022 at 10:47 am

      You are already effortlessly chic, Sherry!

      Reply
  11. Annie Diamond says

    September 22, 2022 at 10:20 am

    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!

    Reply
    • Mary Ann Pickett says

      September 22, 2022 at 10:23 am

      Thanks, Annie…LOVED your foreign correspondent travel post.

      Reply
  12. Candy says

    September 22, 2022 at 9:41 am

    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!

    Reply
    • Mary Ann Pickett says

      September 22, 2022 at 10:22 am

      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.

      Reply
  13. NCSue says

    September 22, 2022 at 9:25 am

    AS always, love your post! How do the Madewell loafers fit? TTS?

    Reply
    • Mary Ann Pickett says

      September 22, 2022 at 9:34 am

      True to size…I normally wear a 7 but a 7.5 if they are pointed. These are comfortable in a 7.

      Reply
      • Mary Ann Pickett says

        September 22, 2022 at 9:34 am

        PS. Thanks, Sue!

        Reply

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