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 Wearing clothes that feel outdated or are overly conservative can send the wrong message.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.

Hi Jennifer, I enjoy your posts. As I’m reading these reply’s it occurs to me that I need to be educated about what pant length is what pant style. In particular what’s the difference in crop, capri and peddle pushers? I apologize if you have posted about this previously. I’m 62 years, 5’8” and live in the heat of Texas, so for me the longer pants are too warm. That said, I don’t like my knees to show. So what is the ideal pant length you’d recommend? Thanks in advance! Do you think this question might be worthy of a separate blog? I can’t be the only one confused about this.
I think is worthy of a separate blog.
Just under the knee is much more flattering than mid-calf. The best length is a spot on your leg where it nips in, and narrows.
thank you!
I am 67 and 5’8”. In the hot summers, I choose casual knit dresses and skirts – typically Talbots (T by Talbots specifically) or Escape by Habitat. Talbots has their Perfect Shorts that have various length options including 13 and 10.5. I gave up capris after reading numerous articles about how unflattering these can be – I really see no one wearing them any longer in my area!
As to capris, they are a style ‘I am on-the-fence about’ as feel it may be not so much their design as it is how they are improperly worn and accessorized, like many others have expressed in their comments. -Brenda-
Jennifer your spot on regarding Capri pants as a garment that age as women. On the flipside of that concept I think it’s really difficult for someone in their 50s + to find stylish dresses that don’t look like something a 20 year old would wear. Especially this summer with all the ruffled sleeves and tiers.
My problem is I live in Arizona where it is extremely HOT. I’m too old to wear shorts out in public – capris seem cooler than long pants. Luckily, I have very thin legs,so I don’t think capris look too bad on me
I am confused about the capri length. I’m noticing some retailers and designers call crops capris and vice versa. If capris are the tight below knee to mid calf length, then I agree this is a look that screams midlife. I purged my wardrobe of these items 4 or 5 years back after seeing photos of myself in them. So unflattering despite my having well defined calves. I did manage to keep the quality cotton loose fitting below calf length ones though as they are comfy in our hot SE Florida summers (April – November). These are cargo style with cuffs, emulating the wide leg look crops so popular right now. With a 27 1/7″ inseam, most ankle pants are full length on my 5’4″ frame and crops fit like ankle pants. Go figure. I’m gathering 5’6″ and 28″ inseam is the new petite.
I wear simple cotton dresses and skirts in warm weather, i hem them to just below the kneecap. When walking I wear shorts about thigh length. When exercising I wear just below knee length exercise leggings. My calves are rather muscular, so I can’t wear any narrow pant, there’s not enough room for my calves, so any pants I do choose are ankle or long. I prefer a more European look ( yes linen) , so I don’t follow my local tribe. I will shop in any store that intrigues me. I do think stores shouldn’t label their “ departments “ , many petite women can wear junior cuts, a good example is a denim jacket. Online shopping eliminates “ departments “ and ageism.
Excellent points, Eileen!
Living in a popular Southern California resort area, I rarely see anyone wearing capris unless they are rocking a 1960’s Palm Springs look. When they do that, it’s usually fabulous but definitely not me. Capris have never been my style & when it’s over 100 I choose a dress or Bermuda shorts. Do you think maybe it’s a regional acceptable style?
I’m seeing a lot of it here in Vancouver, but perhaps they’re tourists?
Hello,
What city and state do you live in? I am asking because when it is 105 degrees outside here in Texas, it is hard for me to look at colder weather clothes.
Thank you for all your great tips!
I am currently in Vancouver BC
At 5’10” I think capri’s look ok on me. Definitely more casual than ankle pants of a long cropped pant, but I’ll wear them along with 9″ shorts and longer skorts. I do agree with the others…I will not wear crops with any shoes other than sleek flat sandals or possibly a neutral Tom’s type of shoe. Great discussion!
To wear capri pants or not, that seems to be the question. We had a garage sale last month and several ladies stopped by who were probably in their late 70’s. They were dressed to the hilt, tons of accessories. But I totally adored each of them and had the best visit. They had an optimist outlook on life and their smiles were many! It’s really made me be so careful not to label anyone because of an idea that something isn’t approved by the fashion police.
I guess if you love the fit of a capri and it works in your life activities, go for it! Life’s too short to sweat the small stuff!
I would comment that I am 5 foot three and size 14 and can’t wear a petite because of my long rise. So the 14 in misses fits well and makes the crops appear fairly long. For this reason I don’t have to hem crops like I usually do misses pants. I do understand your point about wearing longer pants but also enjoy the lightweight fabric that crops have. Could you make recommendations for lightweight pants that aren’t too tight. I would like to wear lightweight pants that look nice with a regular length shirt ( not a tunic). I’m glad you have addressed this topic. Thanks!
So many comments I agree with!
I am wearing a pair of “chinos” as I type and recently undid the folded up hem, based on your earlier posts. When I am sitting it does catch at the widest part of my calf, but when standing, it is much better.
To each their own, but wearing clothing that flatters you and makes others like how you look, I think is important. When I was a first year medical student, nearly 50 years ago, the resident leading our group
(a man) said please dress professionally as it shows respect to even the poorest patient. This happened at the Bernalillo County Hospital in Albuquerque. He did not mean expensive but to look presentable! That comment still resonates with me years later. I have a dear friend who only wears hiking clothes and although I love her and love spending time with them, it is wearing (no pun intended) to see just hiking clothes! Also, it is always fun to compliment someone on their outfit or jewelry.
One more question:
Jennifer last year you went to Palm Springs and had your colors done–I can’t find that reference in your posts—
thanks
I just say wear what you’re comfortable with. At over 60, nobody looks at us much except ourselves.
I don’t wear capris, loose dresses, hats, scarves, costume jewellery as these make me feel old.
We have to dress in what we like for our own tastes and not worry too much.
Great point! If it makes me feel older than I am, I don’t want to wear it.
In Europe I saw linen everywhere, all ages, with high quality bags/ shoes/ sunglasses. In my 55+ community, it’s pocketed cotton capris at mid calf, a loose tee, Merrell sandals, sketchers, matching accessories, nails and hair “ done”.
Stores could add fabrics like seersucker, pique, and 60/40 blends, all washable.
We could learn to love a seamstress.
Maybe we could try on different things, or observe what the younger women are wearing?
Great topic.
I see those same outfits in the US a lot and think we can do better.
I know that look very well. It is common. Not my style at all.
I don’t buy capris. I guess I never thought they looked good on me. I did read women commenting on the way their bare legs look. I use a tanning product and that helps to disguise many flaws on my legs. Surprising how much better my legs look. A secret is my husband is now using a tanner too. Stay cool ladies!
Self-tanner can work miracles, I agree!
Thank you for mentioning capris again. I wore them 15 years ago but never again. Ankle pants and even cropped are a much better choice, at least for me. Short skorts are fun too and hopefully modern.
I prefer cropped pants to capris today but a few years ago capris were your only option if you were trying to hide scarred knees from knee replacements. I don’t find dresses suit my casual lifestyle, on the boat or in the garden. When I wore capris I bought those without pockets on the thighs or drawstrings. Being tall they hit me just below the knee not at the widest part of my calf. I have to agree that cropped pants ( just above the ankle) are more flattering. I hope this trend continues.
I totally concur with your opinion of capris. I have never seen anybody wearing a pair that I thought looked even remotely attractive. I actually purchased a pair to wear to the gym. Thankfully I looked in the mirror before I left home. Off they came and straight to the donate pile they went!
What will I do with all these long tunic tops in my closet?They look good with leggings or skinny pants.Are we wearing these?
I have lots of tunic tops too. If the fabric is thin, they can be half tucked. They’ll also look great with narrow jeans. The ones that are passe now are the ones so skinny that they look spray painted on!