Very Casual Dressing for Women Over 50: Frumpy to Fabulous

My life is pretty casual these days. I spend a lot of time at my computer, reading, walking my dog and experimenting with vegetarian recipes. Many women over 50 have casual lifestyles, but who wants to look shabby, frumpy or sloppy? Not me. Do you ever feel frumpy? Struggle with how to put a casual outfit together?


Pam, Susan, and I have very different Style Recipes™ so our alternatives are all unique. I love to see how they take a frumpy look to fabulous!


This outfit contains one of the worst trends that’s been foisted on women in many years. The ripped, torn, and overly distressed jean. The amount of poison flooding into our environment to produce this product is shameful. Sadly, it’s also a fast track to looking shabby.

Here’s my take on the items in this outfit:

Distressed jeans

Earlier this week, I asked readers on my Facebook page what they thought of distressed and destroyed jeans. Some felt younger women could get away with them. Most said they would never wear them.

I have to agree. My style recipe would never allow me to wear ripped jeans. Even when trending in the ’70s, I sewed on colorful patches to cover tears or rips. Nothing has changed for me.

Frumpy to Fabulous: Very Casual Dressing for Women over 50

I prefer dark wash denim. These are my favorite jeans from Soft Surroundings. I don’t give up style for comfort with these jeans.


Style Tip- Slim or skinny pants look best hemmed to just at, or above your ankle bones.


I’m dressed for my knitting group meet-up. We gather every 2 weeks at a local sandwich shop for coffee, laughs and knitting.

coffee and knitting

It’s always very casual and I don’t want to overdress. I also don’t want to under-dress or my confidence takes a hit.


Flip flops

Some women live in them daily, some hate them. I fall somewhere in the middle. When I wear them I chose cute ones with a pattern or detailing.

Flat sandals need not be plain.
Dark denim wash Metro Leggings from Soft Surroundings

For day-to-day running around, I prefer a sandal that’s more secure on my foot. These sandals are comfortable yet add a bit of sparkle to my plain outfit. I have foot problems so I chose to spend most of my life in flats.


Target T-shirts are inexpensive enought o replace when they start to look shabby.


The t-shirt

I prefer a longer t-shirt and buy most from Target. I tuck the bottom under itself to give a thicker layer around my waistline. Their cotton is nice quality and because they’re inexpensive, I can replace them each Spring with fresh colors. Here, I chose my favorite color, a necklace that matched and a vest, worn open. Everything has stretch, so I’m comfortable. If you’ve read my blog for any time, you know this is very casual for me.


Simple lines, casual fabrics and comfort mkaes a very casual outfit that is not frumpy.

Our chat last Tuesday covered casual dressing for women over 50 and ways to do it effectively. Thanks to all who joined or saw the replay. If you missed it, you can watch it here. We had a lot of fun!


  1. Jennifer, I LOVE, LOVE, LOVE the way you look! It almost brings tears to my eyes. I know that sounds dramatic, but at 54 I have been struggling with my sense of style (or lack thereof.) I constantly assess other middle-age women for both role models and ANTI-role models. I look at what makes them look frumpy to get an idea of what to avoid but I also want to steer clear of that desperate “trying too hard to look young” look. Your whole outfit, hairstyle, accessories, attitude just NAIL it. I have a pair of jeans just like yours that I frequently wear, and I also prefer simple t-shirts with a flattering silhouette and cute sandals like you’re wearing. The vest really pulls it together, though, and gives it a fresh, edgy vibe. I am inspired! Thank you!

    1. I’m so glad to hear from you Lisa! Looking desperate or like we’re trying to hard is sad and unfortunately I see it all time. I’m delighted to be of any inspiration for you!

  2. Can you tell me where you purchased the black vest? The outfit is my style; casual yet put together! And, you do it so well!

    1. I bought the vest many years ago at Nordstrom. It was very inexpensive but timeless. I find those investments well worth it.

  3. I’ll do a ripped jean, but a mild one and with a jacket and good shoes and bag. Never flip flops off the beach. I live in t-shirts from Everlane. A lot of my peers wear activewear 24/7. Anything involving a buttoned pant is dressy!

  4. I was quite surprised the other day when I walked into a teacher colleague’s room and found her wearing a pair of the ripped jeans. I am sure they were expensive but I felt they did not look professional even on a Friday. Unfortunately, this look is all over the schools with rips in somewhat precarious places. Administrators(female) have been seen wearing this look to workshops and conferences. Thank you for showing a more presentable and absolutely appropriate alternative to the ripped jean look.

    1. Those ripped jeans are not inexpensive! It’s a personal choice that doesn’t look chic to me. Other women love them. I assume a school administrator sees students wearing them a lot. That in itself would keep me from wearing them.

  5. Thanks Susan. It’s all about personal choice! We are each unique and our personal style is the same!

  6. Those overly distressed jeans do not look good on anyone I know! Even my tiny little granddaughters!

    I don’t wear flip flops like those but I do wear lots of sandals.Your blingy ones are very cute! One brand called Fitflops are very supportive and come in lots of styles. More comfortable than most sneakers!

    I just found your blog through Fifty not Frumpy! Liking this series!

    1. Welcome Linda. I haven’t heard of of Fitflops! I’ll check them out.I’m so glad you’re enjoying this series!

  7. Sue Petersen says:

    Finally, I have found a blogger who dresses more like me! I wear casual most of the time as I am retired and live on a farm. I dress mostly in t’s and jeans on a normal day but dress up more as required by the occasion. I also don’t wear heels because of foot problems. You show how to look great in a casual outfit! Thanks.

    1. Welsome Sue! I’m so glad you’re here.

  8. Angela Fisher says:

    I love your outfit! The sandals elevate the whole look. What is the brand of the vest? The whole look is super cute.

  9. I like your outfit Jennifer and how it’s put together. No flip-flops, cropped whatsoever, neither that awful handbag. I don’t own ripped jeans though if I had to wear them, I would combine them with a chambray shirt, a classy navy blazer, ankle boots and a nice handbag.
    The attitude is also very important. Thank you for your collaboration with Pamela and Susan and your blabs.
    Nice week-end.

    1. Thanks Catia. I’m so glad you’re enjoying our Blabs!

  10. That jeans looks very good on you and I love the color of the tee.!I love flipflops, I have got a beautiful pair with Golden strings and glittering, but I cannot walk with them that far lol! Have a great weekend!

  11. I agree about frumpy. I refuse to go out like that. On the other hand I have been known to stay in my PJs and bathrobe while trying to get a blog out our another project completed. Granted absolutely no one sees me and I refuse to look in the mirror. Let’s see, I just drove my son to the office ( long story) and I’m wearing leopard spotted flats, loose nike light weight sleek sweatpants that are so cool I’d wear out to dinner and a grey and white striped cool sweatshirt and a poka dotted scarf. So I figure I look ok if I ran into you on the street.
    Now the other thing. I’m starting to become a vegetarian also. Any books or recipes you really like?

    1. It sounds like you looked fabulous Sandra! I am a fan of “Oh She Glows” cookbook. I will start adding some posts on what I eat 🙂

  12. I couldn’t agree with you more on the ripped jeans! You look darling in your outfit. PLEASE keep this type of post coming!! So helpful.

  13. May be TMI, but what kind of underpants do you wear with these? I hate panty lines and don’t feel conformable in a thong. I’ve been struggling with this forever! Thanks

    1. Giilian O’Malley from Target. They make an underpant that has very thin edges and leaves no lumps 🙂

  14. You seem ti have hit a chord with the mention of foot issues,. I too have this problem and wold like to see a review of nice sandals and flats that you would recommend. And, how about sharing some of those vegetarian recipes! Thanks!

    1. I will start including more of my vegetarian recipes. The post on comfortable sandals that look nice is a great idea. Stay tuned!

  15. Great look, Jennifer! The dark jeans look great! And I love your fun sandals, cute necklace, & vest. It’s often the little things I think that make the difference!

    Have a wonderful weekend!

  16. You’re coming up with some excellent columns or ideas for your blog, I’m truly impressed. Taking frumpy to fabulous is fantastic especially coming from you three. I sure hope you’ll still love me and be my friend when I admit after seeing your first feature outfit I thought, now that’s my kind of comfort, haha. I actually wouldn’t wear the shorter tee shirts but I have my share of torn jeans (sorry about the environment, that was good news for me to be aware of) and I wear them all the time, usually with fun heels. I totally agree with the flip flops, they’re only for the boat. You look absolutely so put together and fabulous! I promise I’ll leave my torn jeans home when I come to visit you?

    1. It’s all about personal choice! Every woman’s style choices are her privilege and what makes us unique! The ripped jeans don’t work for me. End story, As an Image Consultant I appreciate that all women deserve to dress the way they want!! I’d be thrilled to see you if you showed up wearing a paper bag…which of course you wouldn’t!!

  17. You look fabulous! Thanks for the tip about the Target tees. The sandals look great…a little bling is always fun!

  18. Love your style tip on the tee shirt, turning the hem under. I am not a big tee shirt wearer, but your style with the vest is so cute.

  19. Even the word, “frumpy,” is frumpy! LOL! No thongs–feet or tush–or ripped clothes. I’m with you, girlfriend. Brenda

  20. Jennifer I agree with you on all counts and though casual, you are completely chic!
    This is a fashion look I wear a lot! Have a great weekend!

    The Arts by Karena

  21. Please help! Shoes…doomed to not just flats but, orthopedic flats. Getting dressed for Easter Brunch was impossible. How to scale, match, blend clothes to ugly shoes?

    1. I hear you Tee! I wore orthotics for years. I’ll do some posts on footwear for the confort challenged 🙂

  22. I feel the same way about distressed jeans. I love the vest over this casual outfit. I am also a dress for comfort person.

  23. Carol LaRochelle says:

    This is MY kind of casual outfit, which fits my lifestyle most of the time. As far as the foot problems, I can sympathize, as I have a real,problem with this respect, therefor I am always on the hunt for attractive sandals, wedges, etc. I do not want “old lady” shoes, and I mean no disrespect for anyone that has to wear orthopedic shoes. I really know your pain.

    Are these the metro leggings from soft surroundings? I have been wanting to order these? Do they run true to Size?

    Love the vest, what brand is this if you don’t mind answering this question?

    I love your blog and read it almost daily.

    Thanks for your input!

    1. These are the Metro leggings which I think run true to size. I put mine in the washer and dryer which shrunk them a teeny bit. They went right back into shape after. My vest is mamy years old, sorry.

  24. That’s a great look on you and pretty darn youthful, too. It’s funny how familiarity with ripped jeans, meaning seeing them everywhere, makes us think they’re ok. I wouldn’t buy them though.

    1. You explained it perfectly Carol. Their familiarity has had a huge effect on people’s perception of their value.

  25. Linda Robertson says:

    I love your blog and your style. I live on an island off the coast of South Carolina and try not to fall into the throw on anything to go out the door category.
    I am not into most of the social media. Is there anyway I can listen to you and Pam and Susan without being on Twitter.
    Thank you for continuing to give me inspiration

  26. You look very casual & put together. I’m going to invest in Target t’s!

    1. They’re really great quality for a short term investment! I find t-shirts get tacky pretty quickly so I won’t spend a lot of money on them.

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