What To Wear Over 50: A Gentle Style Reset That Starts With You
Thereās no shortage of advice out there about what women over 50 should be wearing. Most of it feels outdated, patronizing, or clearly written by someone whoās never dressed a real body in midlife…let alone tried to button jeans after a sushi lunch.
Iāve learned that as we age, our lives shift, our bodies change, and our wardrobes need to catch up. What used to be your go-to might suddenly feel too fussy, too flat, or just… vaguely irritating. That doesnāt mean your style is gone. It means your clothes need to meet you where you are…not where you were ten years (or ten pounds) ago.
These are five things Iāve embraced in my own closet lately. Theyāre not rules. Just gentle updates that have made getting dressed feel a little easier, a little more current, and a lot more comfortable. This post has been very popular, so I’m updating it for new readers to discover.
1. Add Texture and Pattern (They’re More Forgiving Than You Think)
Shiny, smooth fabrics tend to catch the light in all the wrong places… including ones I didnāt even know I had until I caught a glimpse under dressing room lights. Thatās one reason Iāve started leaning into soft textures, especially near the face.
Textured fabrics like tweed, slub knits, matte crepe, or nubby cotton all diffuse light instead of spotlighting every fine line. And pattern plays a quiet trick of its own. Small, tone-on-tone or scattered prints soften contrast and give the eye something else to focus on, so it doesnāt land directly on wrinkles or shadows.
You donāt need to wear a head-to-toe pattern if thatās not your style, but Iāve learned a patterned scarf near my face can brighten things up without overwhelming me.
Try this: If a top looks a little off, notice the surface. Is it too shiny? Too smooth? You might not need a different cut, just a fabric with texture or pattern that flatters your features instead of fighting them.
2. Rethink Black (Especially Near Your Face)
For years, black was my go-to. It was easy, it was everywhere, and it always felt āchicā…especially when I didnāt want to overthink what I was wearing. But somewhere around my late 50s, I started to notice it wasnāt doing me any favors.
As our coloring softens with age, black can start to feel too harsh. It deepens shadows, exaggerates fine lines, and has a sneaky way of making us look more tired than we actually feel.
This doesnāt mean you need to banish black altogether…I certainly havenāt. But Iāve become more thoughtful about how I wear it. I try to opt for navy, charcoal, or deep taupes. When I do wear black, Iāll wear it further from my face, break it up with a scarf, bold earrings, or a jacket in a better color.
Try This Mini Style Experiment:
Hold a black top and a navy or charcoal one near your face in natural light. Compare how you look. Is the black draining and overpowering you? You can learn more about intensity here.
3. Choose Comfortable Shoes (Without Giving Up Style)
Letās be honest, most of us have spent decades in shoes that were more about looks than logic. High heels, narrow toe boxes, zero arch support…our feet didnāt stand a chance, and we’re paying the price for it now. Here’s how to make your shoes more comfortable.
I used to think that comfortable shoes meant giving up. Now I think the opposite: Iām not giving up anything; Iām just not willing to be in pain by lunchtime.
The good news? Comfort brands have come a long way. There are plenty of stylish options now with actual arch support, cushioning, and toe boxes that donāt require origami-level foot folding. Sleek loafers, modern sneakers, and ankle boots with low heels exist, and theyāre worth seeking out. I have an entire category on comfortable footwear options here.
What I do now: I shop with a clear boundary: if they pinch, slip, or make me walk funny, theyāre not coming home with me. No matter how cute they are.
Take a look at the shoes you reach for most often. If the same two pairs are always in rotation, pay attention. Thatās your closet quietly telling you what actually works for your life right now.
4. Makeup Should Support You, Not Work Against You
Makeup after 50 isnāt about doing less; itās about doing what actually works now. Our skin changes, our features soften. What once looked fresh might now feel flat, harsh, or simply… not right.
I used to wear foundation every day. Now? I lean toward tinted sunscreen or a sheer moisturizer with a hint of coverage. It smooths things out without settling into lines or making me feel overdone. Full-coverage products tend to sit on top of the skin, and Iāve found they often emphasize what Iād rather not highlight.
These days, I focus on what helps me look a little more awake: softly defined brows, a touch of soft eyeshadow, and lipstick that brings some color back into my face. I still wear blush, but I apply it a bit higher than I used to, and I go easy on powder because anything too dry seems to age me faster than time does.
If your makeup isnāt quite working for you anymore, donāt scrap it all. Try just one change like a brighter lipstick, a dewier base, or a lighter hand with your brows. One small update can make everything else fall into place. You may also enjoy The Best Fall Lip Colors for Mature Skin
5. Curate Don’t Accumulate
I wish I could say Iāve stopped falling for every shiny new trend, but the truth isā¦ I still get lured in now and then. Itās easy. A bold color, an āitā silhouette, a sale… it all whispers promise. And sometimes it works, but more often, it ends up in the donation pile or hiding in the back of my closet.
You may also enjoy 10 Common Shopping Habits That Sabotage Your Wardrobe
What Iāve learned is that chasing trends doesnāt always lead to better outfits. It usually just leads to more stuff and more confusion.
These days, I try to be more deliberate. I still enjoy knowing whatās current, but I filter it through my actual life and what I wear most. What feels good, flatters, and plays well with the rest of my closet.
Before I bring something new in, I ask:
- Does this fit the life I really live?
- Can I wear it at least three ways?
- Do I feel like myself in it?
Try this: Take a look at what youāre wearing on repeat. Those pieces are already doing the heavy lifting. Let them teach you something before you add more.
If this post resonates with you, I would love you to subscribe and join our community here.
Why This Matters
Style after 50 isnāt about reinvention; itās about recalibration. Your life has shifted along with your body, your calendar, and maybe your tolerance for anything that digs in or rides up.
If somethingās been feeling off lately, donāt assume itās you. Itās not.
Start small. Your closet is full of clues. Sometimes all it takes is a quiet morning, a good mirror, and a little coffee-fueled honesty to realize itās not you thatās the problem…itās the clothes that arenāt keeping up.
Now Iām curious, ladies…whatās one thing youāve changed in how you dress after 50?
Thanks for reading, and remember to wear what makes you feel confident and fabulous!
Clothes that skim the body, not hug it. Thank you for your tips.
Hi Jennifer. I love to hear your honest and sassy reviews. That helps me from going into the into the store and buying stuff that I don’t need. Can you point me in the direction to find your
1. Your facial products that you use daily.
2. Your make up.
3. What kind of sunscreen do you use? Mine is tinted but makes me look too yellowish.
Thanks for all you do behind the scenes.
Iām working on an update, stay tuned.
You make lots of good points. I have started adding more navy to my wardrobe. It is hard to find dressy pants that are not black. I love a good scarf to brighten things up and tie them together. I gave up high heels many years ago though I do have a pair or 2 of kitten heels. Thanks for the inspiration.
A really helpful post, thank you. In my 70s my body has redistributed itself and although Iām not overweight, I now have a tummy and thicker waist. Luckily there are many styles of pants and jeans with elastic in the waistband, which means I can still wear my regular size. It took some adjustment to cope with this change, but now Iāve learned to accept where my body is thereās a sort of freedom. I can still look good but be comfortable as well
Thank you so much for sharing this! Many of us are in the same place.
I’ve been feeling like I’m dressing too casual lately and might need to something I can wear for dressier occasions. My outfits are mostly jeans and tennis shoes and golf clothes. I’ve been trying to tone down my makeup too. i also love the scarf with your black top. Thanks for all the great ideas.
Nice casual is a challenge to dial in just right for our individual lifestyle and personal taste. I struggle with it often.
How does the No Makeup Makeup work over sunscreen?
Beautifully!! I wear the porcelain shade.
Can you link the white jacket in the last picture?
This is my fleece jacket but the color I’m wearing is sold out.
Thank you for your Common Sense approach to dressing!
We can dress beautifully and still be comfortable. And casual does not mean frumpy. I am over 50 (closer to 70) and enjoy planning my wardrobe, knowing what colors and styles are best for me and my life style. Each day I put on my makeup and dress as if Iām joining friends for coffee or lunch. Look Good=Feel Good!
Thank You,
Bobbie
I agree! Everyday is an occasion
Good morning, Jennifer. I think the biggest change I made was starting to dress for me instead of slavishly following the entities who decided what was “in” or “on trend” or “age appropriate” for the season or year. This doesn’t mean that I ignored clothing that was appropriate for specific occasions, just that I wasn’t going to get rid of my pretty hats because the fashion was baseball caps or that I was going to cut or tear holes in my favorite jeans or run around town in sweatpants and hoodies, etc. I’m currently going through my closets to see what still works or doesn’t work for me at age 64. Some will be altered, some donated, and others will being staying right where they are. My hats are going nowhere except on my head, however.
I LOVE this Christine! Thanks for inspiring us all to stay true to our personal style.
Where did the light blue jacket with fringe come from?
That jacket is here. I love it.
Perfect tips today! You always have the best for your readers. I turned 70 this summer and I am playing more with my foundations and blushes to even out my tones. Once summer’s slight kiss of color fades, it takes a bit to adjust.
I love the grey fringed jacket you’re wearing at the top of the post. Can you share what brand it is please.
My jacket is here.
Good Morning Jennifer: Great article.
Thanks Jennifer for another great post. I have been following you for years because of your thoughtful insights and I have learned a lot as well from your dressing room try on sessions. Now at 75 with silver hair I favor navy and grey over black that dominated my wardrobe in the past. Always short waisted with collapsing disks I now am even more so – once 5’7″ now 5’5′ – so proportion (thanks for your recent post on that subject) is what I focus on most. I’m loving the current trend for cropped tops and jackets – just what I need.
Iām leaning further into navy too!
After 2 decades of black, I was just tired of it and it wasnāt doing me any favors. I still have some, but rarely wear or buy it. Navy and chocolate brown work for me now. Iāve also added a bright piece to almost every outfit. A casual Talbots jacket in true orange (goes with navy and brown!) gets more ālove itā comments than anything else I wear. A extensive collection of scarves helps with this. Creative, artful necklaces also get a lot of positive feedback. Blessed with good skin (for my age) so NoMakeupMakeup lightly applied has been a find. Pricey, but I use so little it will last at least a year. Their āless is moreā advice is certainly true for me.
Bravo Teresa!!
My huge paradigm shift came after retirement. The need for office attire diminished and the need for casual wear increased. The result was a lot of bad choices that felt kind of off. Three years in and Iāve paired my closet down (three bags of clothes headed to donation) to core basics that flatter my pale skin and gray streaked hair. When I get dressed I feel like my new self. I then did the same to my make up and what a revelation that was. Four items do it all. Tinted sunscreen, switched to dark brown mascara and a plum eyeliner, lipstick that matches my coloring. If any of this sounds familiar I think I owe some of it to reading you blog! š
Retirment wardrobes are a challenge. It sound like you’ve nailed it Diane!
1) Knee length skirts instead of above the knee after 50
2) 5 cms heels – mostly square
3) Be more aware of my posture
Oh yes, my posture needs constant reminders.
Thanks for showcasing the Talbots gray leopard print velveteen pants. I ordered them immediately! Love, love, love! I think they’d look great on you as well.
I don’t wear short skirts or shorts anymore and try to avoid sleeveless shirts (difficult in Florida where I live) because crepey skin is real at age 69.
This is very helpful thanks. After working all my life and wearing professional clothing I find it difficult to change.
But I do dress for myself not anyone else
Kelly
Good for you Kelly. Dressing for ourselves is powerful!
Iām 73 and I live in Florida. Iām tall and was thin most of my life. Able to wear pretty much anything I wanted. Now not so much. Of course my body changed and although Iām not heavy, everything doesnāt look good anymore. Iāve stopped wearing sleeveless tops as my upper arms arenāt great now. I prefer pull on pants and crops as theyāre more comfortable. And no more shoes that are not supportive and comfortable. Iām in the midst of purging my closet and it actually feels good! Thanks for letting us know weāre not alone in this!
You are in very good company Debbie! I’m glad you’re here with us
Thanks for the great reminders in your post today. The one advice you mentioned again, “is your wardrobe reflecting your life style today.” I am now a care giver for my precious husband. I am home more, shopping and appointments are the main activities of our life. I have also changed my makeup and now wear tinted moisturizer, really like it alot.
Thatās a tough job, Audrey. Take care of yourself too!
Your post was perfectly timed for how I’ve been feeling lately. It’s a balancing act between trying to recapture my past life’s makeup and wardrobe and my current lifestyle where many women have just given up. After years of being on the corporate treadmill, it’s sometimes hard to wake up and realize you have no place to go and nothing you have to do. I don’t want to surrender to that mindset and that’s why I look forward to reading your posts.
I was just thinking about that Suzanne. My stay at home life is so relaxed but I refuse to give up.
your style is approperate for myself I hope I am now on your mailing list for emails even if it is the wrong season me.thanks Joanne
It would be nice to see some photos/pics of the examples you give in each section with a link to your favourites. I am starting to wear navy blue now (I am 59) but am short. Only 5ā2ā so struggle with trousers etc and due to HRT I have got the typical muffin round the Middle. So I am conscious of wearing T shirts that cling so tend to hide under baggy T shirts and loose shirts. Any suggestions xx
Any suggestions on how to cover age spots on my legs
I think self tanner works wonders!
I should have known I wasnāt alone!!!!! How absolutely brilliant to read the comments of like minded ( and like-aged) women. At 72, Iāve had a major life change ( sold house with garden, moved into townhouse) For this past Covid year, I was prepping house for sale, packing, then unpacking and renovating new place, so Iāve been living in paint-covered stretchy things for just on 15 months!!! Now that Spring has arrived ( in BC, Canada…..not that hot!) I am desperate to have a fresh look, albeit a size larger!
Jennifer, your advice is spot on ….I am looking forward to more inspiration for the next part of my journey and reading comments and experiences of others like myself.
Welcome Susan! Weāre happy to have you here
Very interesting article and feedback comments, I still need to feel more confident with what I do. Maybe when the pandemic is over.
Love what I’ve seen in this site so far. Excited to learn more from you.Karen
Iam glad to hear all your comments I like to where shadow but got stuck on blue don’t have any friends that where make up so it’s hard to get help.need a foundation to cover without looking like iam trying to hard to hide my flaws and a shadow that doesn’t clump in the creases iam a mess can you help also on a very limited buget .
I recommend a tinted sunscreen which does double duty for you.
(Age 65)
I have been a Shiseido user for 10+ years.
I have been a recent convert to Future Solutions foundation (previously used a Lifting foundation) and it is fabulous, be aware you can easily apply too much, great for dry skin and a little goes a long way. The real superstar is the Minimalist Powder Blush, the container resembles an eye shadow compact, but it has the most amazing effect using so little. I also use eye shadows as eyeliner placing more on the inner corner to highlight. Viola, a sweep of mascara and lipstick, done.
Next step, getting my hairdresser to cut my curly grey locks short, so ready to get rid of the aging hippie look.
Have a beautiful day, sister girls.
I am 85, and I have worn makeup since I was fifteen. I still wear foundation, and yes I do have some deep forehead wrinkles which I do not like. I have always looked 10 years younger (I have been told). My skin is very un-even (Face) What should I do?
Love your hints.
Are you using Retin A? I find that the most beneficial. You could also talk to your dermatologist about a mild peel.
Tender skin I have tried Este Lauders camouflage.. covers everything! You might want to give it a try.. it may dry fast you can add some moisturizer
I am older and refuse to dress like an old lady. Good for you. You go,girl.
I would love to not wear foundation , but I I have broken capilliaries on my face . Any suggestion ? Qk
There are many lasers that will zap the capillaries and make them go away. Check with your dermatologist
A while back, Jennifer highlighted a makeup called āNo Makeup Makeupāā¦.a creme that went on with a soft brush. I tried itā¦it really covers those broken capillaries I have on my cheeks, but still looks natural. Jones Road also makes a tinted moisturizer called āJust Enoughā that does a fairly good job on covering them. Finally, Perbelle CC Cream is a heavy lifter for me on days Iām outdoors a lot. It has SPF 43 in itā¦and a little goes a long way to cover my capillaries and still make me look like me.
Laurie, I agree with you on the Perbelle CC Cream! I’m a big fan of it for days when I need to wear foundation (I’m 56); I even got my 79-year-old mother using it now, and she loves it, too.
Good tips I just efitedy closet and will go through again with your tips in mind. Love tge make up tips…I had given up on make up altogether once I turn 52 because what I was doing ageded me…girl from the 80’s. Now I will make another go with your tips in mind. So happy to see what TO wear over 50 and not anotherthe don’ts
At almost 81, and fair like Jennifer, I was very pleased with No Makeup Makeup. I brush it on those places where my skin has a need for blending and not all over my face. This is a very nice subtle makeup. On most days eyebrows in blonde done lightly, a little Merit Cheeky cream blush higher on my checks and creamy rose lipliner, then Natural Fusion lip moisturizer in color Glisten. Ready for my day. Less is more as we age and the good thing is it is easier to be ourselves and not try to please the anonymous other.
YES!! Great point Sydney
I find np matte lipstick to be very drying on my lips. Can you recommend a brand that feels moisturizing? Thanks Jennifer for the good tips.
Karen H. – try Thrive Cosmetics (online), they make a moisturizing matte liquid lipstick.
Thanks Christine! Iāll check it out.
Good tips! I do wear foundation over a primer. I do invest in great products that look and feel good. I also wear eyeshadow, eyeliner and mascara. I do think we can look faded as we age and need colour. Lipstick is lighter and sometimes brighter and not the dark colours I always loved. I also wear coloured eyeglass frames (currently purple). I have fun wearing costume jewelry. As for clothing, mostly I wear an attitude.
I love this Janet! Wearing things with attitude makes all the difference.
I still use foundation. I like Giorgio Armani’s Luminous Silk. It’s lightweight and has a large selection of shades. Like you, Jennifer, I’ve deepened my eye makeup, topping a lighter cream shadow (Younique) with a darker soft powder (Thrive) and blending well with a brush, and have moved to a deep plum lipstick (Burt’s Bees). Also creme blush in apricot (Peek). I’m strawberry blonde, and just had my hairstylist weave in bits of gold, copper, and red shades. I receive more compliments on my appearance now. I enjoy sharing with and learning from friends and others at my workplace.
Your hair color sounds rich and glorious! It’s so fun to play with colors and experiment with new products.
Fantastic ideas! I never knew that textures belong near the face! I will keep that in mind!
You are so right about the foundation and the creases. I only use a tinted moisturizer now. Yes, and matte everything! Those sparkly things just make any lines more obvious. I have friends my age who have given up makeup entirely, but that won’t be me. It’s a matter of finding what works to enhance the face without looking theatrical.
I won’t ever give up wearing makeup either Kay. I find it fun and love to play with it.
I havenāt worn foundation in years. I opt for a multicolored blusher instead. It gives me a hint of color while still evening out my skin tones.
Great advice… love those shoes btw.
Terrific idea Cyndi! Evening things out is important on my skin.
Cyndi – What brand and actual color name of multicolor blusher do you like to wear?
Yes to texture but not heavy texture on the bottom half. Great tips!
You always have the best style information for us over 60 women. Thanks so much, Jennifer! If I wear black (rarely) I put a light scarf by my face to help with my complexion changes. One issue I’m having is my neck getting red welts (allergy??) from, I think, jewelry. Have you heard of this? I only wear 14/18k now and still have issues. You are a treasure and I appreciate your perspective!
I have the same problem in recent years, Cheryl. Those lovely statement necklaces are no longer wearable. I do love my gray pearls, cool and smooth.
Oh you should check with your doctor about having a nickel allergy. My original wedding rings were in white gold and I noticed that I would develop blisters and itchiness usually on my left hand. Overtime any white gold I had could not be worn as it caused welts or in the case of my ears, weeping. I packed it all away and the skin sensitivity went away! I wear an id lanyard at work and one day commented to my dermatologist that I had this crazy itch on my belly…she looked at it and said that it looked like a nickel allergy! Of course the cheap base metal of the lanyard clip (which hung low on my torso) and the white gold all have nickel as a component. My dermatologist told me to ditch the white gold and the lanyard and just clip my id to my shirt and the itch went away! I have had the diamonds reset in yellow gold as well as any white gold earrings and the jeweller put a yellow gold plate on the back of a beloved pendant that caused big welts on my chest when worn. I rarely were costume jewelry unless it is nickel free and no, that old tip about painting the ear posts with clear nail polish does not work. Nickel is absorbed into the body and you may not react for many years but believe me after suffering with the equivalent of a second degree burn on my left hand I was happy to finally find the answer…and I now have a lovely yellow gold and diamond ring because…I did keep the man!!
Jennifer, I stopped wearing foundation two years ago and switched to CC cream. It has sunscreen, cream & a light tint, just enough to give a touch of colour. I also tried a bit more colour on my lips. I normally wear a nude, plum or mauve. This summer I tried pink. Not a light sweet pink but one more towards a fushia. Red is still too strong a statement. I feel silly wearing it but the day may come when I find the courage to step out in red. Ha!
I still wear an all black column (top & pants) but top it with a colourful scarf or jacket. I find the column of black is slimming and is a blank canvas for other colour.
An interesting thought on smooth fabric and itās effect on our wrinkles. I do like my leather jackets. Iāll have to do an experiment. ????
Great post! As for foundation, I switched to Bobbi Brown serum foundation. I find that it smooths and moisturizes. Give it a try!
Sounds great Gail !
This was a great post Jennifer…so true about heavy foundation settling in lines…yikes! Agree about brighter lips…now if I could just get rid of those lines around the lips!
Those lines are such a challenge. I have lots or them too so rely on my lip pencil to keep lipsticks from sliding.
I think I have written this tip before, but some lip filler can sharpen the lip lines and prevent lipstick bleeding. Plus a good injector can use a little bit of filler on the vertical (or smokerās lines) as well
Some good advise here! I’m just starting to play with darker make up colours xx
I agree about foundation going into the lines on my face but I need something to even out my skin tones (notice the plural). Any thoughts?
I wear tinted sunscreen Dottie. Tinted moisturizers are a great option too!
Yes to all five points! I gave up foundation makeup some time ago, but occasionally I wear Bobbi Brown’s tinted moisturizer which doesn’t “settle” in wrinkles so much. Just the other day at the grocery store, the young check-out woman said to me, “I love your red lipstick, but I don’t have the self-confidence to wear it.” So, people do notice our chosen makeup statements. I struggle to find eye shadow. Any suggestions? Also, I recommend Vionic shoes.
I am a huge fan of the Tarte pallets which come in lots of tones. My favorite is the nude Basics 2 Naked pallet which is cool toned and totally matte…https://rstyle.me/n/c3juvc39zw
Wonderful ideas!
Love your black and nude mules. Very chanel-esque! Who makes them?
xoxox
They are a few years old from Marc Fisher and available here http://shopstyle.it/l/TFNA
Great tips, Jennifer…I do all of these. Great reminders we should hear often.
Love All the Tips!!!! You hit the nail on the head with each one. Might try the on; stop wearing foundation, never thought of it that way in which it “enhances” wrinkles, but will try it!. I also like to “add-in” a bit of trend myself, a scarf, belt or shoes, I feel special and in style. My shoes have also gotten a bit shorter in the heel. I feel more confident when they are on-trend too. Thank you for all the Tips.
Iām glad you liked them Holly!
Shoes…used to be my favorites! I wear 7.5 an easy size to find in great looking shoes, but today it’s about comfort, comfort, comfort. I wear a lot of active wear for that very reason! (Don’t like sneakers/running shoes with stylish outfits). Happy to hear that shoe companies are taking notice!(I do have a nice pair of Bernie MeV which are comfy). Trends! I tend to add simple touches of trends….a black belt with a bit of leopard on front….same with a nice black slip on shoe.
Thank you for covering this topic!
Itās no longer n option for my feet to suffer for the sake of fashion.
I use Doll 10 ‘this covers everything liquid filler’. I am an 81 year old redhead with a bit of redness on my cheeks. This in the light shade and a bit of blush. My husband says my complexion glows. You can cover as little or as heavily as you want. I don’t use very much and I also use it as my undereye concealer.