Monday Musing: The High Cost of Trying to Fit In
Happy Monday, ladies. Over the weekend, I took my twelve-year-old grandson clothes shopping. He’s growing fast and is pretty clear about what he doesn’t like to wear. As we walked through the mall, he looked at me and said, “I don’t care about fashion, Granny.” He was dead serious.
And yet, he spent an hour making sure his new hoodie looked exactly like the ones his friends wear.
At twelve, fitting in is a survival tactic. But for women over 50, we often still shop with that same “safety first” mentality, even if we don’t realize it. We dress to blend into our neighborhoods rather than risking anyone thinking we look overdressed.
Suburban Overdressed Myth
Dressing well means dressing to please yourself. But how that message is received depends a lot on where you live. Part of the problem is that today, the “average” look has become so casual that anything with a collar or a finished hem feels overdressed to some people.
Take the outfit I’m wearing: a cashmere sweater and polished pull-on pants. In some circles, that’s enough to get a “Oh, you’re so dressed up” or “Where are you going?” comment.
It’s a comment that can make you want to apologize for your own closet, but you shouldn’t. When people say that, they’re usually reacting to their own discomfort. Your effort makes them feel a bit too “seen” in their own casual wear, and that friction is what prompts the remark. They’re looking for a reason…a lunch date, an appointment, a party…to justify why you don’t look like everyone else.
But as a personal stylist, I know the quilting on the jacket and the sneakers are what save it.
The quilted texture is inherently casual, and the sneakers are the universal signal that I’m off-the-clock. Without those two elements, I might look like I’m headed to a board meeting. With them, the look is intentional but relaxed. It’s the difference between looking stiff and simply having high standards for your weekend wear.
STYLISH QUILTED JACKETS
Why This Matters
Style isn’t about seeking validation or “fitting in” like a twelve-year-old at the mall. It’s about being intentional. When you understand the “why” behind your outfit, you stop being vulnerable to other people’s comments. You aren’t “too much”… you’re just you, and you have a logical reason for every piece you’ve put on.
Applying This To Your Wardrobe: The Personal Stylist’s Eye
If you ever feel like your outfit is a bit too sharp for your environment, you don’t need to start over. You just need to dial back the formality of one or two elements. This is how you maintain your style without feeling out of place.
- Utilize Texture: A quilted jacket or cabled sweater automatically grounds “serious” items like cashmere or wool trousers.
- The Shoe Shift: Trading a shiny, pointed flat for a soft suede sneaker is the fastest way to dial down an outfit’s formality while staying chic.
- The Layering Rule: Choose a cotton or silk tee instead of a crisp blouse under your cardigan. It removes the “office” vibe but keeps the quality.
- The Accessory Pivot: If a structured leather satchel feels too formal for a casual lunch, choose a high-quality canvas or leather-trimmed tote instead.
These small shifts are the filter that lets you wear what you love. You aren’t changing who you are… you’re just dialing back the formality to suit the setting.
Style Without Permission
This shift from seeking validation, like my grandson at the mall, to dressing with pure conviction is exactly why I’ve been thinking about French style.
We love to reduce it to striped shirts and effortless hair, but the real thing runs deeper. It’s about presence and dressing for yourself, instead of needing permission. It’s also built on a foundation of restraint and buying better-quality, but fewer, clothes. When you stop chasing trends and start investing in pieces with actual substance, you stop needing to apologize for how you look.
That’s why I was so struck by French designer Simon Porte Jacquemus naming his 79-year-old grandmother, Liline, as the first ambassador for his fashion house. Not a model. Not a celebrity. His actual granny.
It’s a choice that felt quietly radical. In a culture obsessed with youth and speed, he chose presence over performance. Liline isn’t stylish because she’s older. She’s powerful because she doesn’t have to try. There’s nothing self-conscious about her elegance and no need to explain it, shape it, or soften it. It just is.
Real French style has always had more to do with restraint than reinvention. It favors pieces with shape, substance, and longevity. It reflects how you live, not what the internet says you should want. This moment reminded me that style, at its best, isn’t about perfection. It’s about knowing who you are and not needing anyone else’s permission to dress like it.
The Take Away
Style isn’t a math equation, and it certainly isn’t a search for suburban approval. It’s the outward expression of an inward reality. Whether you’re twelve years old, trying to find your tribe, or seventy-nine and becoming the face of a French fashion house, the lesson is the same: the most stylish thing you can wear is your own conviction.
Don’t apologize for being the best-dressed woman in the room. Don’t dim your light to make others feel more comfortable in their hoodies. Buy the better sweater, wear the polished pants, and add the sneakers that keep it real. When you dress for yourself, you don’t need to explain the “why” to anyone. It just is.
Have you ever had someone ask why you’re so “dressed up” when you were just wearing a favorite sweater? How did you handle it? Did you apologize, or did you just own the look?
I’ve been telling people that say you’re so dressed up that I am trying to match the inside to the outside. Sometimes it’s inside/out, sometimes it’s outside/in.
My, did this rile me up. How’s about I wear my pretty shoes and carry the handbag I love and forget dialing back? I live in a large urban area with lots of retail choices. It’s one thing to see youth going back to grunge and baggy jeans, but that is not a reason to live in baggy jeans and sweats when you’re older. It doesn’t carry the same fashion defiance. I am tired of going places and seeing other people dressed like they are doing chores around the house. Seriously, recently some family members attended an evening wedding celebration at a steakhouse, all wearing jeans, sneakers, and sweatshirts. If they’re comfortable with it, fine. Yes, they asked why I was dressed up. I was wearing slim pants, nice top and completer jacket. Not a cocktail dress, but even business casual was considered over the top by some at this event. Shouldn’t the question be, “Why are you so casual?” But of course that would be rude. Ironic. Don’t expect me to dress down because others are overly casual (dare I say frumpy?). I enjoy my clothes and dress to please myself. At 65, I don’t know how much longer I can wear heels, and I am not giving up early just to “fit in.”
Really useful and thought-provoking post!
I think you recently discussed using a pop of color—-that is also a great formality-shifter.
this post resonated with me. a few years ago i moved to a suburban community in the denver area where the “uniform” seems to be baggy shorts and oversized tshirts. not my cup of tea. i dress very much the way you do. not long ago one of my neighbors saw me and said, “where are you going all dressed up?” seriously? jeans and a pretty sweater with loafers? i replied, “i am not dressed UP. this is just how i dress.” okay, maybe a little rude but i’d had it with the comments.
It’s so easy to be caught off guard by those comments. It really does speak to their discomfort but I refuse to let them make me feel uncomfortable.
I retired from teaching in June. My school had a business casual dress code which was respected by the faculty. Since my closet was mostly work clothes I decided I was going to continue getting dressed every day – not as formal as school, but definitely sweats and jeans. People have commented on how ‘nice’ look, especially since I am not wearing jeans all the time. I am confident and glad about my choice.
Own the look ladies
Your topic today was very interesting and one I can easily relate. I have always enjoyed fashion and style. One of the comments I often get is “you always look so put together”, to this I just say thank you. I am a 77 year old woman who is fortunate to sew nearly all of my clothing, thus I’m the canvas for my creativity. I agree, we live in a very casual society, but it is the little things we can do to set us apart. I never apologize for being dressed.
That’s wonderful!
Today’s post really hit home with me. I do like to dress up, but I find myself dressing down because I know others will. Thank you for the suggestions to make me feel more comfortable about my choices!
When someone tells me you are so dressed up I say “thank you!” I am tired of going to nice (expensive) restaurants and being with slobs. Have people lost their dignity?
Haha last week I wore a blazer with non jeans (I think the drawstring Billie pants from Old Navy), a scarf and loafers to the office and people asked me why I was so dressed up. (People also suspect you are interviewing for something!) I just said, nah, I’m just wearing what’s in my closet and I’m cold! (We recently “returned “ to 5 days in office). For me there has always been another wrinkle. As a professional woman, that jacket has always signaled position. It says, “I’m the lawyer.” Now at my office everyone knows who I am, but outside it’s a different story, even in these casual days. I’ve always struggled with looking professional versus being approachable (not looking like a “snob.”) I think that’s what you are addressing here. In the end, it all goes back to being comfortable in one’s own skin! French (or for me NYC, a bit less feminine) style is a great starting place.
Those signals are important when working. Your outfit sounds great!!
I have a lot of wrap around skirts, made from recycled saris, which look more dressed up than they really are. When someone asks me why I’m so dressed up, I just say this is comfortable and I feel good when I’m wearing it. Usually, I pair them with a t-shirt rather than a nice blouse, and that works well too.
Those skirts sound magnificent. Where do you find them?
Oh, this post resonated with me! I am almost always the most formally dressed person in the room or at an event. It’s an interesting cultural phenomenon. I actually live in an upscale city in Florida, but I summer in a town in coastal Massachusetts. In Florida my dressed up look is much less likely to be commented on because here, the women as quite stylish and up to date. In Massachusetts however, if I don’t look like I fell out of bed in Barbour and Patagonia I’m asked why I’m so dressed up. Frankly, I could care less. I don’t want to “dial back the formality.” I dress for me and me alone, and I am always more comfortable dressing in a more formal manner. I wear a lot of dresses and prints, and this makes me happy. I am comfortable with the way I dress, and I NEVER apologize for the way I look. If it makes someone uncomfortable, that’s her problem, not mine. Always be true to yourself and you’ll be happy!
Terrific column! Thank you.
This is why I enjoy reading your blog. Thank you
My pleasure, Wendy
Thank you for this. I’ve been dealing with balancing “my style” with the expectations of retirement living in Florida where shorts, sloppy tee shirts and flip flops are more common than not. I’ve slowly weaned out my corporate NYC wardrobe and have finally found my comfort and style 10 years later. I still get the occasional “where are you going?” but I now smile and answer “no where.”
Great information and reminders! I don’t remember ever having to “apologize” for how I’ve dressed but I am conscious of where I am going and who I’ll see. I still, however, dress primarily for me. And if that means I’m wearing a favorite “elevated” outfit, so be it! I’m never over-the top but strive to be comfortable and feel like “me”.
What a wonderful post today! I will look up the french designer and his grandmother, love that. I have slowly started to dress in what makes me happy and have figured out the styles that I really enjoy wearing. It has been a years-long process and ongoing but I’m okay with that.
It feels so wonderful to figure it out. I’m still changing and with it, my style choices.
I always dress for myself
Wherever I going I dress my best for me not anyone else. When I am complimented I just say thank you. You need to be comfortable in your own skin.
Sad that we even would have to worry about being “too dressed up” when we’re really not. I refuse to dress “down” to make other people feel better about themselves. It’s not that hard to make a little effort.
Thank you for putting into words what I’ve felt but have not been able to express. So good.
This is a terrific article by you. Meeting once a month with a group of ladies I noticed how extremely casual the dress was by the other ladies and for me getting a bit dressed up was part of the fun. A chance to wear clothes that made me feel good and not just leisure wear that is prevalent. I’ve noticed lately the ladies have been dressing up a bit more too. Why not as we don’t have the opportunity as much in our late 70’s.
Indeed, and if we don’t wear them now, we’re wasting the opportunity