Dressing with Intention After 50: Style, Visibility, and Showing Up as Yourself
During a recent conversation with a long-time friend, the topic turned to style. We both live in areas that tend to skew very casual, and frequently find ourselves surrounded by a sea of leggings and sweats. As a result, we often feel as though we stand out, just by dressing with more intention. It got me thinking (again) about our comfort levels with visibility and style choices.
This article was originally published on August 28, 2024 and has been updated to include current looks and relevant product suggestions.
Why Authentic Style Is an Act of Confidence — Not Vanity
Women over 50 often speak of feeling invisible. While our society is undoubtedly ageist, I do think that personal style can be a way to show up and stand up for ourselves. To be visible, and work toward changing the narrative.
When we dress authentically to feel like our best selves, we will feel and project more confidence. And I believe that in presenting ourselves authentically and unapologetically, we free others to do the same.
Breaking the Cycle: Small Style Risks, Big Confidence Gains
Visibility can be a double-edged sword though. Some of us were raised to prioritize conformity, or have experienced a lot of criticism about our appearance. Or maybe we’ve experienced pressure not to dress “better” than our peers. If so, dressing in a way that stands out (whether intentional or not) can be uncomfortable. “The nail that sticks up gets hammered down…” etc.
It can become a vicious cycle. The more we feel insecure about our appearance, the more we tone it down. And the more we tone it down, the more insecure we can feel about being visible. Breaking out of the cycle can sometimes require taking some risks. They don’t have to be huge, flamboyant risks. It can be something as simple as adding a fun accessory or two, or swapping out your wear-everywhere sneakers for a pair of cute flats. Little by little, you can build upon these to increase your style confidence.
When Blending In Is Actually the Right Call
(Caveat: I do think there are times when blending is a valid choice rather than a capitulation. For example, when I travel I usually tend to dress in a way that’s more understated. And I take into account regional norms. It’s not about “trying to look like a local,” but rather just not calling attention to myself as a potential target.)
Looking Intentional Without Trying Too Hard
Our style doesn’t have to shout for attention or embrace the latest trends for us to be visible. An outfit that looks neat, put-together, and intentional can go a long way.
My sizes: Tee – Small, Pants – Petite Small
When we dress authentically to feel like our best selves, we will feel and project more confidence. And I believe that in presenting ourselves authentically and unapologetically, we free others to do the same.
What do you wear to feel more visible? Let me know in comments!
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Lovely, sweater coat. Where I live dressing simply is the outlier/attention getter. The bright, patterned and adorned is the norm.
When I wear my decent black loafers with darker jeans and a blazer over a newer tee, I do feel more respected. ( I’m the one doing the respecting!) but I do get into that super casual rut too- my comfy light jeans with a sweatshirt or hoodie or old tee shirt and my sneakers.
Because our basement flooded recently and it stinks now ( someone is heading here in a day to bleach clean cement floor) I’ve been reverting to clean- up clothes, old and raggedy as I’ll toss them out once I’ve sorted through stuff…
Tomorrow doing my hair and I’ll feel better!
We’ve had floods in our basement too. No fun! I don’t fret much about what I wear at home. There’s always outside and messy things to do, consequently I’ve ruined many clothes, but your uniform sounds like one of my favorite outfits.
I really enjoyed this post. In the sea of leggings and sweat pants, dressing nicely can really stand out and set a better example. Our quiet confidence and style may become something others might want to emulate.
This is very true, I live in a suburb of London, there are quite a few people who have obviously taken care with their outfit, but yet more (and its mostly younger people) in the same uniform of gym wear…Contrast to visiting Central London where its a shock to see men in suits and women in business attire.
Great article. In my very casual area I do try to step it up a notch, but not too much. Even jeans and tees look and feel better when ironed, (crazy?) and a nice leather bag or tote is essential. It takes no effort to add some jewelry and a cute hat. And a smile! I feel more seen than if I dressed just like the ultra casual younger women. Makes all the difference in confidence, and I get better attention and service from those I’m doing business with.
I could not agree with this more! I find that even a minor effort to my appearance on a casual day (hair, outfit, jewelry), just enough so that I feel good, makes a huge difference in my attitude, how I perceive the world, and how others treat me in return.
What a terrific post Susan! I intentionally dress almost every day in a way that feels pulled together. Even if I am popping out to the drugstore or running other errands I still take the time to pull an outfit together. This way I use my wardrobe and accessories instead of saving them for special lunches or outings. I dress for myself so I feel good about myself. And I find others respond better or more positive to you if you make that effort for yourself. I am less invisible to others because the effort shows.
I love this type of post Susan – thank you.
Love this comment. I live in quite a laid back town and I still dress for myself with a scarf or earrings, lipstick and leather shoes occasionally instead of sneaker slipons all the time. Makes a difference!
Your words are mine too and it makes such a difference to my health and wellbeing. Even if feeling lacklustre, just applying my makeup lifts my spirits.
Here in New Zealand, there is a great affinity for black, but thankfully, colour has always suited me best, which in itself, provides an uplift.
I also echo, Susan’s posts hit the spot.
I agree completely. I live in the northeast, where many women are dressing in dark toned athleisure . I finally have the time and money in retirement to shop and spend some time putting outfits together, and I really enjoy the process.
There are two things I use to be visible. My jewelry and my shoes. I always look for conversation pieces in my jewelry made from interesting materials. And while my stiletto days are over, I have embraced comfort with a twist in my footwear. I make choices to look different, because IMHO different always outperforms trendy.
I have a minimalist style, but switch it up with shoes and bags. On a recent trip, I made a point to look around the airport and notice who was wearing what. It was pretty interesting, and not so much in a good way. I did chase down a woman who had a cool, bright orange crossbody phone bag — score!
Thank you for the inspiration and insight, Susan. Lovely post.
Susan, I so enjoy reading your blogs. I am almost always the dressiest one in the room but I don’t mind, I have cultivated beautiful pieces through the years and sprinkle in trending accessories or update my shoes/boots. I feel like I get more respect when I make an effort to pull a look together. I feel like yoga pants should only be worn in the gym. When I look nice, I feel good about myself.
Great post, Susan! I live in a very casual area in southwest Florida. And, it is quite hot and humid. I wear long linen shorts on most summer days but style my shoes, jewelry, and blouse with intention. No flipflops for me unless I’m at the pool.
The photo of you wearing your sweater blazer shows it to be much lighter and brighter than the J Crew website. I’m a spring also. Which source is most accurate. I’m totally in your corner when it comes to giving my appearance a bit of extra thought!
Everyone’s monitor may display colors slightly differently, but IRL the sweater jacket is a mid-navy. Not super dark or bright.
A very thoughtful and thought provoking post, Susan. I rarely feel “invisible” even though I’m 80. Crazy as it seems, I think hair color, posture and self-confidence is every bit as important as fashion choices in daily life interactions. After reading this post, however, I’ll pay a bit more intention … maybe I just haven’t been conscious of interactions which feel dismissive. Hmmmm …
Marta, I agree with your thoughts on posture and self-confidence as they relate to fashion choices. In fact, I think they all interact in a positive way, which seems to reflect Susan’s statement “When we dress authentically to feel like our best selves, we will feel and project more confidence.”
Susan, this is why I love your blog so much. You’re the only blogger I follow who has mentioned blending in when traveling so as not to attract the wrong kind of attention. Years ago, my husband met someone in a professional setting, whom he didn’t know. The man mentioned he had seen us on a flight he took and proceeded to describe my engagement ring! That taught me that people you wouldn’t expect to do notice what you’re wearing. I live in a mid-size metropolitan area where crime has become a big issue, so unfortunately,“blending in” has become even more important to me.
As a young woman I learned to never leave the house unless I was well dressed and had my makeup on. That has proven to be beneficial as I often receive compliments.
I’m new to your blog and love it. We are never to old to learn.
This post really resonated with me! As a retired person, I’ve gradually let go of the beautiful, but now mostly “over-corporate”, clothes I wore to the office pre-COVID. I took a lot of pride in how I looked at work. Building a comfortable (I have very sensitive skin and hate any itchy fabric) wardrobe for my retired life has taken awhile, but I feel so much more confident when I add jewelry, a belt, and well-chosen shoes to a simple jeans and tee outfit. Love your style and your posts!!
Since retiring 6 years ago and moving from NY to CA I have finally rediscovered my fashion groove. What does not work for me is wearing golf clothes all day long or these bright, patterned prints that seem popular with ladies of my over 70 crowd. I’ve always been confident about my style and clothes but I went through a period of feeling too preppy out here. Through you I have learned to embrace my style with jewelry, fun shoes and a good jacket or sweater. Walking taller with a smile also helps!
I’ve had a change of heart recently. I may not choose to emulate Iris Apfel, but I also don’t want to blend in with the wallpaper. I’ve found myself wanting bolder choices. I came across a brand whose slogan is to the effect “that you already have enough basics,” which is true, at least for me. Consider it.
I always start with my hair. Now that I have joined the country of white haired people, it seems it is less forgiving and requires more grooming. Wispy fly away hair on top of a poor cut immediately makes me think of an invisble little-old-lady.
This post really resonated with me. When I was young and very self-conscious, I wanted nothing more than to blend in and be unnoticed. Now, at 71, while not flamboyant by nature, I don’t mind being visible. I’m comfortable in my own skin and I’ve chosen authentic as one of the adjectives to describe my personal style. The others are classy, casual, comfortable, and confident.
I have felt invisible myself. But I made a major change in my health and wardrobe beginning in 2022 as my husband’s health took a bad turn leading to his death. I decided to take better care of myself, changing my diet, my exercise habits and my wardrobe itself.
This change also changed my “visibility”. At age 70 I have gotten more compliments about my appearance and my style — from young people to my contemporaries — than I’ve had since I was in my 30s! I feel like myself again.
Your article coincided with reading about coming across as intimidating if you take care with styling your outfits from existing clothes in your wardrobe and therefore look coordinated. You made a reference to that sort of reaction and to be aware – a helpful insight.
I love your outfit today! It’s not overdone, but with nice touches. I especially love your belt! I used to wear belts a lot, but now that I’m in my 70s, I don’t know what to do about this tummy I’ve never had before. Things look fine from the front with a tuck or belt, but from the side, it seems so noticeable. So I mostly wear tops that covers it, but that often seems sloppy and not as polished as I’d like. Any advice??
Hi Susan, thanks so much! I’ve always had a bit of a tummy, so I share your conundrum. I’ve found you can downplay the focus on that area a couple of ways. One is to go with a pants style that’s a bit relaxed, or has some ease in the stomach/hips. I also find that a half tuck rather than a full tuck can help create a diagonal line from the side rather than a horizontal one, if that makes sense.
Very thought provoking … I have several random observations.
– I was in Newport on Saturday with friends, and the area was packed with younger women in long (maxi-midi) dresses … and hats. They were just lovely.
– My friend was dressed casually, but she has money for clothes and good jewelry, so she tends to be noticed.
– At my farmer’s market, the 40-ish woman in front of me stood out from the rest of us: bronze jeans and a royal blue tee shirt. The colors made all the difference.
– I’ve been wearing columns of neutrals (white lately), and it seems to me if that makes me more visible.
* Out with my lovely daughter to eat and I am invisible to any male waiter lol
Good post and some excellent recommendations, tho I found it so depressing to read the sad reality that in my 50s, while I felt as though I was in my prime and turning heads, I was likely invisible. Thankfully my attitude is still intact a decade later.
A lovely post, Susan!
As a 29-year old woman who follows (and adores!) your blog, I love how you empower us to live bold and turn our ears away from an ageist society trying to convince us to quiet down and hide as we age.
I work as a nurse in a field of medicine where I am often seeing patients of young ages (20’s and 30’s) experience illness and death. I now recognize the privilege, the gift it is to age and gain years of wisdom and experience, and it breaks my heart when older people tell me, “You’re young, enjoy it. Life ends when you turn (insert some arbitrarily young age)”. It’s just not true. Style, enjoyment, LIFE can be found at any age. Looking forward to the next post!
S.E., I love this, thanks for posting. I started reading this blog when I was under the demographic age range and found it very useful. And now…I’m approaching retirement and feeling genuine affection for my clothes and style.
This was a great article, Susan. I’m loving all the comments too!
Thanks so much, Esme!
I love the sweater blazer, but concerned it may be too straight for my pear shape. Is it very straight or does it flare out a bit so I would likely be able to button it all the way down?
When I practiced law, I didn’t feel invisible except when standing a in a group of taller men (I’m 5’3) so I often wore clothes to stand out a bit from the men – red or bright tops/ blouses under my suits, or burgundy suits in addition to my gray, navy and black suits. I’m still adjusting to dressing in retirement.
Hi Mary, when I button the sweater blazer and lay it out flat, it seems to have a slight A-line shape. Narrower at the shoulders than the hips, though not full, like a “swing” shape garment. It hangs mostly straight on the body.
Hi Susan,
I love your blog. This one was a great post, I agree that one dresses to respect /adapt to ones surroundings. I have worn different clothes in Paris , on Anguilla, in London, Scotland and the south of France. I like to reflect the culture around me and find it’s a fun way to enjoy my trips!
I live in a small tourist town out on the eastern end of Long Island, and the influx of many from New York City now enables me to dress up or down, depending on what I’m doing. My daughter and son-in-law and grandkids live in lower Manhattan and I dress down to play in the park or attend a sporting event, or up to go to the Met and/ or a show or dinner. I also am very active in theatre locally so with my theater friends and at rehearsals I can let my more colourful and creative personality come to the fore. I think it’s so important to make an effort to be dressed appropriately but it doesn’t hold me back from showing a bit of my own flare. I just love how you discussed this in this post! I love your travel wardrobes. Thanks for being there in my day to make it more fun. And brighter.❤️
I don’t think that I am invisible haha. But you are right in your assessment.
And I love your blue blazer.
Greetje
I feel that I started dressing as my authentic self in my 50’s. I’d call it organic-classic-casual. Before that I felt restricted by “dress codes” in various parts of my life. I remember going shopping in 2020 and being the only woman in the entire mall who was wearing a nice sweater blazer, jeans, and booties. Everywhere you looked was a sea of sweats and leggings but I felt unapologetically myself. I could have never done that in my 20s-40s. I would have felt I needed to conform. I love short hair styles but I just look better with shoulder length hair. All through my business years I felt I had to keep my hair chin length to fit the business mold. I didn’t want to be seen as attractive or draw the wrong attention. Thankfully that is not a thing for my daughter’s generation. She looks beautiful and stylish at work and has a high level position in her company because she is judged on her skills. I’m glad that conforming is not as important as it once was. I love getting dressed as who I authentically am each morning. Thank you, Susan, for setting a good example of that for us.
I laughed when I read your statement about not standing out too much when travelling. It reminded me of my extensive European travel in the 1990s. In one photo I am wearing a pale grey silk trouser suit (in the club lounge) all of my diamond rings, a very expensive watch – looking very glam. Fast forward to my European holiday in 2023, and it was a pacsafe handbag, casual trousers with a tee shirt and uniqlo puffy vest. No jewellery except cheap pearl earrings. Now I am 67, I am at ease with what I wear, which is generally gym gear during winter (I walk everywhere) and a linen dress in summer, When I am doodied up, I generally receive a lot of compliments- probably more due to shock on their part.
Now in my late 70s and having worked in an era that had ‘dress code guidelines’ I feel it definitely taught myself to take pride in one’s personal overall appearance that IMO has proven to be beneficial, as can rightly say that ‘I have never felt invisible’. -Brenda-
Susan, this post resonates with me. I love style visibility, and feel like it is a way to remain vibrant even as my body’s vibrancy diminishes with age. It is an act of expression, and is an artistic outlet for me even as my career path skews un-artistic.
One question: I tried on the Warwick blazer you are wearing in this post. I adore it and was so excited to incorporate it into my fall/winter wardrobe. However, I’m 5’3″ and the length of my arms is proportional to my petite stature. The sleeves on this blazer were so long on me! I am probably oversensitive about fit, but I ended up taking a pass on the blazer and am still feeling pangs of disappointment. I think this blazer looks terrific on you. Did you cuff or roll the sleeves? I can’t tell from the photo. If you cuffed or rolled the sleeves and it still looks that great, it gives me hope that I can wear it too and should give it another try with a less poison eye about sleeve length.
Hi Rock, thanks! Yes, I cuffed the sleeves (rolled up once about an inch) and would also wear them pushed up.
Good Morning. I live in a town voted least fashionable, Durango, Colorado. Think Carhartt, Patagonia, Prana and Keens. We can tell who are the tourists quickly by their attire. I love clothes and get frustrated by the lack of style here. So I dress up when I leave town or buy simple garments in better quality. Being over 65 I’m invisible to most anyway. Standing out has been difficult in the past. Tuning out others perceived judgement is necessary for me as life is too short to wear ugly clothes!
I “ditched the dye” during pandemic, to find pure platinum silver hair underneath—I get compliments from strangers every day—not invisible any more!
Up until recently I did seasonal work as a tax preparer. I was temporarily assigned to a different office. I was not happy about leaving my usual location but to cheer myself up I made a special effort to look put together. The office was pretty casual – nice jeans were ok – but I intentionally added accessories such as scarves and interesting jewelry. Taking the time to add extra touches to my look made me feel better and several coworkers complimented me over the course of the assignment.
Great outfits. Casual and elegant, very well put together.
On the point of visibility…I don’t have to worry about that haha.
Greetje
Timely post for me! Yesterday I bought a “ lady jacket” in a linen floral. I love jeans, tee & a blazer or cardigan. I hesitated because of “ why are you so dressed up” syndrome. Then I said- I adore this and it makes me feel good!😊
I’m no shrinking violet…I’ve always worn my winter colors whether they are “in” or not, so, yeah, that’s me in the red. But related to what you mentioned, my company has “returned” to the office and people are really mad about it. We became “casual”during Covid, but now people are really pushing it, wearing sweatshirts, leggings, ratty shorts, etc. to the office. I recognize it as a form of protest, and power to the people, but I don’t dress that way and I really stick out in nicer clothes, or gasp, a blazer! I just tell people I have a closet full of nice clothes and I’m going out o wear them. (We were hybrid before coming back in full time.) Again, I don’t expect people who now have additional day care and commuting costs to also buy a new wardrobe, but I’m also gonna do me. Dressing as a lady lawyer has always been fraught. You want to project authority and professionalism but also be approachable and not scare people! Chag semeach!
Great post, and very relevant, Susan. I love clothes, and now have the freedom to wear beautiful things that make me feel good. With a full social calendar in southwest Florida, there are plenty of opportunities! One area I still struggle with is my hair. I went natural many years ago but am blessed with beautiful salt and pepper streaks that bring a lot of compliments. My issue is styling in a way that looks youthful (as I feel at 71) without looking too haphazard. It’s a challenge.
For travel, I rely upon some Anatomie separates, (in navy and gray) that give me a polished look, but super comfortable, and change up the looks with scarves. I wear basic jewelry while traveling and try to not stand out.
I think invisibility is more of an issue for petite women. Greetje has it right: she doesn’t have to worry about it both because of her wardrobe and because of her height. I don’t do a lot of accessories, but I try to be intentional about what I wear. Your posts have been especially helpful lately as I am shifting some from sneakers to shoes and adding a necklace or scarf for New England’s still cool (and damp) weather.
I use color to make myself stand out a bit. I prefer trim classic casual style clothes but I punch things up with jewel tones (winter) and especially clear reds against black or navy or white. The beige-y neutrals and pastels are not for me. I’m small and petite so I could easily disapper in a crowd without colors. I know some people are loathe to wear bright red but I feel comfortable AND noticed in it. Plus I always add jewelry, even to the simplest grocery shopping kind of day. Love your blog, and your little doggie always photo-bombing your pix!
My go to’s are a pop of red lipstick, a scarf, a vibrant color top that compliments my skin tone, fun shoes or a piece of clothing that has a unique detail. I am retiring from the corporate world this week and looking to reinvent myself. Oh boy!
Excellent article, Susan. Good food for thought.
I’m interested in that green cardigan you’re wearing. It looks so nice on you. I am a Spring, like you (HOC), and I’m nervous that the color isn’t exactly right for me. It looks more “ Autumn “ to me?? What do you think about the Brilliant Cobalt color in that same cardigan, for a Spring? There is no J Crew near me and so I have to pay return shipping 🙁 so I’m always leery of ordering from them.
Thank you!
Cathy
Hi Cathy, thanks very much! I’m a “Golden Spring,” so am on the warmest end of the Spring palette. The Brilliant Cobalt would work well for a Blue Spring (coolest end of the Spring palette).
I have yet to come up with the “3 words” to describe my style (but I’m trying!). I would say my style is guided by “standing out while fitting in”. We also live in an area that’s pretty casual. And since Covid especially the world has gotten more casual (too casual, IMO…..even in our own family). But I can usually anticipate the “dress level” that will prevail and try to take it up a notch or two.
Please take this in a “good way”. Your recent hair style reminds me of Doris Day. She was adorable and always looked turned out. Always enjoy your posts.
Hi Susan! Another great blog. I really like your idea of showing your style in small ways: acute pair of shoes; a pair of earrings; a pair of glasses. Those happen to be my choice and showing my style with everything else being a sort of minimalist approach I love the fact that there are more retailers offering petite sizes and cropped tops shorter tops for short-waisted women.
Your little dog is darling. She is often near and seems like such a loyal companion.
Thank you, Linda! She really is.
I live in a smallish southern town. So really, no matter what I wear, I will be visible . I would say that color tends to make me most visible. For instance. I have a Sam Edelman hot pink puffer coat. You can’t help but notice it! On the opposite side of the spectrum, I have a Theory gray double wool coat. It was an NAS purchase. It may not be colorful but the lux quality of it makes it a standout. Perhaps making thoughtful choices in my color season, and taking time to style my clothes (instead of just wearing them) is always going to draw attention because most people just get dressed. Thanks for your emphasis on color, Susan. You do a marvelous job of translating it for Real Life!
Thanks, Quietgirl!