Ageless Style vs Fashion Only Midlife Women Wear
I often talk about classic, timeless fashions. The simple cardigan, white shirt, ballet flats, loafers, trench coat, and straight-cut pants all stand the test of time. They can look as current today as they did 20 years ago. Boho fashion also has its timeless essentials, as do preppy and traditional styles. Today, I want to talk about some fashions only midlife women wear. As always, my goal is not to convince you to give up wearing something you love. I hope to help you become aware of the messages your clothes are sending so you choose with intent.
As I go in and out of some of this community’s favorite retailers lately, I am occasionally struck by some of the unfortunate fashion they’re offering. This topic has been on my mind more and more lately, and lo and behold…I see we’ve discussed this before…so let’s dig a bit deeper.

You may also enjoy- An Easy Guide to Boho-Chic Wardrobe Essentials.
Our style evolves as we age, but that doesn’t mean we should embrace clothing that makes us look older than we are. Fashion is a tool for self-expression, and regardless of our age, it’s empowering to choose outfits that reflect vibrancy, individuality, and confidence. Wearing clothes that feel outdated or are overly conservative can send the wrong message. Conversely, outfits with juvenile prints can unintentionally undermine the polished image many older women want to portray. The overly puffy sleeve has been an unfortunate trend lately, and few women over 60 can pull it off well.
Since people judge who we are by how we look…dressing in ways that embrace a modern look and personal flair allows older women to feel visible, relevant, and celebrated. We need to wear fashions that reflect our personal style recipe, work for our lifestyle, and complement our body shape. I also firmly believe they should bring us joy.
By this age, many of us have tried and true brand favorites that we rely on for the fit and styling we like. That makes shopping easier and life simpler. However, and this is a big one, just because we appreciate and trust a brand to carry our aesthetic doesn’t mean we can go into the store with a carte blanche attitude and count on everything they offer to work in our best interest.
Fashion that puts women in an identifiable age bracket is not ageless, timeless, or modern. For example…capri pants. I’m not talking about cropped pants, but capris that stop at the widest part of your calf. Despite their resurgence among the young last season, they only seem to proliferate at retailers that cater to midlife women. See also Are Capri Pants Out Of Style For 2024.
In the same vein are tee shirts and dresses in tiny, childlike prints we might expect to see in the toddler section.
Ageless dressing means choosing clothes that accentuate our best parts and subtly camouflage the ones we don’t want to draw attention to. By our age, we’ve got plenty of body parts we’d prefer to cover, but I’d like to see us doing it with styles that people can’t pigeonhole into an age bracket.
One could argue that silk scarves and brooches also date us because young women have not adopted those accessories. And you would have a point…except they’ve been worn by some of the chicest women in history.
I have no problem looking my age. I just want to look like the best version of myself and dress in a way that keeps me visible and modern. I’ll admit that I find capri pants one of the most unflattering garments a woman can wear, so I have a clear bias. I also steer clear of most prints, but that’s my personal preference. By this age, we’ve earned the right to wear whatever we please. So, if you love capris, by all means, wear them with pride. If teeny, childlike prints ring your bell, enjoy them. Just be aware that they may visually slot you into a distinct age category.
Let’s talk about this. What are your thoughts?
Thanks for reading, and remember to wear what makes you feel confident.

Well… I see I am in the minority here, but then I have always marched to my own beat. I LOVE capris, and for those that live in very warm climates, OR, just like the look they serve a purpose. I love a capri length legging that I can throw a top on with, add a ballet flat or cute sandals, and then run quick errands. It is a pretty basic everyday wardrobe for me, YET, when going out to lunch with friends, meeting up for drinks in the late afternoon, or gathering for dinner, you can wear cropped pants of all sorts, skirts, dresses, slacks or anything else your heart desires. If it fits YOU that is what YOU need to wear. I do agree about matchy-matchy “dated” outfits or anything “boring”. I am 70 and embrace everyday. It’s taken me sometime to get here but I am uniquely me. I so enjoy your page Jennifer. Merry Christmas and Happy Holidays.
Being unique is amazing!
Just wondering what puffy sleeve tops you are referring to?
Overly puffy and short with ruffles like you would see on a 4 year old.
I live in SW Florida and prefer dresses or skorts because of the heat. It is almost impossible to find casual dresses that aren’t sleeveless, ruffled or in loud tropical prints. I still want to look modern and stylish, but not like I’m wearing my granddaughter’s dresses. I wish retailers would realize the untapped market of women our age who can afford to dress well!
We speak with our shopping dollars so hopefully they are listening.
In my opinion, nothing beats a midi length linen dress on a hot humid Illinois day, with sleeves, please.
Give me sleeves too! 👍🏻
Well, I am swimming completely against the tide here, because I like capri pants! It is so darn HOT here in Florida, that capri pants are a must! Also I cannot wear nice cute shoes because I have to use orthotics in my shoes and have done for 30 years! I do wear loafers in the winter. So, I probably look frumpy or whatever. But at this age, my 70s, I don’t have much choice! Some adjustments have to be made for age. One thing I will never wear that I feel is very aging, is pointelle cardigans. And cardigans at all. If I need an extra layer here in Florida, I grab one of my many denim jackets.
Our physical limitations are certainly crucial to consider, but I believe we can also look modern.
Jennifer, you said what needed to be said, and it goes much further than capris ( which I haven’t worn for at least 15+ years and was shocked to see you all still debating). Modern is the key word for me (in fact, one of my “three” words). You have to make some tweaks to look modern – shorter tops, longer, wider pants and jeans. Not oversized like a 20 year old, but in a way that flatters you. Tunic tops, leggings, skinny jeans, novelty prints, all look dated. The overly embellished stuff does too. While I commend many of the retailers loved here for their broad size ranges (I’m petite) in my opinion, Talbots, J Jill and Chicos aren’t modern. Each has gems of course. A Talbots petite blazer fits me like no other. But if you want to be modern you need to branch out to other brands like J Crew, Banana Republic (and factory stores, esp BR), Eileen Fisher, Aritzia, COS, &Other Stories, Quince, Everlane. I also love AllSaints but it’s edgier. As always, wear what you love and what flatters. For me that’s modern, simple and sporty. The three word thing (coined by Allyson Bournstein) really helps.
I agree, Shari. Sizing is a huge issue for many women, but let’s not toss out style just for something that fits!
I totally agree that most capri pants are unflattering – honestly, on almost every age. And as for the excuse of wearing capri pants vs full length to stay cool, I will quote my adult son: “Mom, do you really think that extra six inches is going to make a difference?” It’s all about fabric, ladies! Fabrics that stay cool will be fine in the full length pant option.
Ha ha, your son is right! My thoughts exactly.
Wow…. I’m on the east coast and sipping my coffee a little after 7 and I can’t believe the number of responses you got and pretty much the same consensus. The fashion industry is missing a large segment of the population…….Merry Christmas!!
Good morning Jennifer – Great column this morning. I agree with all of comments. I do not wear capris. I don’t like my “very pale and heavy legs) showing from the hem to the shoes. Looks frumpy on me! Your husband’s comment to help you find a hair stylist struck home! When we relocated to northern Michigan, I actually asked women I did not know, and who I thought had great hair styles, who their stylist was. All were happy to chat with me. That is how I found my stylist 8 years ago. Unfortunately, she is now semi-retired but is still seeing 5 of her loyal clients. Wishing you and all of your readers a wonderful holiday season!
Replacing your hair stylist is hard!! I’ve learned to put my trust in her.
Finding the collection of scarves in this post was like a Christmas gift for me. I love scarves and wear them often. Sometimes I think they date me, but I’ve decided I’m fine with that. My Mom and grandmothers would love them. It’s like a piece of them I’m wearing.
I also find that being “put together” well is noticed by others but not commented on. I’ve decided I am okay with that, too.
Again, then you so much for the featured scarves. So unique and beautiful.
Merry Christmas!
I’m so glad you love them too!!
I am mid60s and find certain capri pants very flattering-the ones made of stretch fabric that are fitted. The capris made of other fabrics that do not fit as tightly to the leg and stick out at the bottom are not flattering at all. I have also worn the athletic knit type fabric shorts in the “bicycle “ length, slightly above the knee, and again they are flattering. Of course the appropriate length top is important. In hot humid weather I need cool! I have had a knee replacement and have no issue with my scar, so if it shows it shows. A testament to medical advances and a part of my life. And yes, footwear is a problem!
Yes I do agree there are done truly unfortunate ( love that word!) styles hitting my regular stores and boutiques. Barrel legpants ? . I do despise skorts on me along with capris, though I understand their need in very hot weather. I tend to wear cropped pants, with wider leg (cooler) or I may venture into sundresses despite my creepy arms. Ugh.
I like cropped pants much better than capris, but cropped and ankle-length pants haven’t been in style all that long. It takes me a while to convince myself to give up perfectly good clothes in order to update my look. Since I retired, I have updated and expanded my casual wardrobe, and this blog has really helped me make more trendy choices and helped me ditch my “dated” looks. Thank you, Jennifer!
I live in Arizona and with our heat (and my legs), capris are a fact of life. I am careful NOT to wear them with athletic shoes but nicer sandals or flats. The heat here starts in May and goes until October, and even cropped pants are too hot at 118F. Unfortunately my legs are not my best feature, and it’s hard to find a longer short (oxymoron!) these days. I think capris can be done correctly but it’s all about proportion and balance, as well as a sleek cut (no bling or buttons, etc.). I run things by my 30-year-old daughter, who is honest with me if it’s too “old lady.” As in all things, to each his (or her) own!
I agree! Wearing long pants here in Florida is just awful! I love capris. If you see my comment above, I have to wear sneaker all the time because of orthotics, so the cute sandals are not an option for me. But there are so many nice sneaker styles now. And I always wear nice jewelry and carry a nice bag so I think accessories do help.
I totally agree with SuzanneGabrielle. Perhaps that’s because I’m also 5’8″ and probably of a similar build. The important thing with capris is to ensure that they end either above or below the widest part of your calf.
I’m with you, Jennifer. Capricorn pants arent flattering on anyone. Another thing that I greatly dislike is the short puffed sleeves. They only belong on six year old little girls.
Show me the difference between cropped and capri? Is there a difference?
You always look great.
I think the reason we see so many capri pants on mid-life women is that they’re the ones with the time and the mobility to be out in the yard or scuffing along the beach, and don’t want damp/dirty pant legs sloshing along their legs.
Now maybe every pair that gets sold doesn’t end up in the garden or on the shore,but functionally I think that’s how we see ourselves when we include them in our wardrobe.
So capri ladies — put’em on and go to it!
I am still on-the-fence when it comes to Capris as feel it may not be so much their style as it is the way they are worn and accessorized, as many of others in their comments have expressed. i.e.: Incorrect sizing and footwear being the biggest offenders. -Brenda-
I would perhaps put shirts with 3/4 sleeves in this category too.