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?
Q: “Why are you so dressed up?”
A: “Because I CAN!”
I’m living my best life and getting dressed is part of my creative process, my armor and my vibe. No apologies!!
If not NOW, when?
Once again a great inspiring post. Your Amazing and your thoughts stay with me in a great way!
It’s funny, I was just thinking about this yesterday as I got dressed to meet with a couple of friends to attend a play. My friends and I have different styles, but we seem to dress at the same level of care and accessorizing. However, I do have a couple of friends who I definitely feel that I need to bring my best look forward when we get together, which is fun!
How nice of you to take your grandson shopping! I wish your grandson well – a lot of unwritten rules at that age when fitting in with friends.
Great article and comments. I feel you should either compliment someone or not say anything. I had gotten awfully sloppy in my dress after retirement and weight gain. A couple of years ago I decided to ‘up my game’ and start doing better. In the last six to nine months I have had some interesting comments I didn’t know how to respond to. The first was in the spring. I had on beige linen pants and a white button up top. Someone commented, “Aren’t you bright today?” Another was this fall. I had purchased a pair of wide leg jeans (not excessively wide). I wore them to a women’s gathering and two women said something similar to, “Look at you in the trendy jeans!” No other comments either time.
YES, all my life…where are you going. After work. Etc. but I pay attention to what I wear. Always have. As a child I got hand me downs or. Oír of cords from the do op if there was $ left after groceries!
Loved this post and its comments, Jennifer. Thank you for sharing!
Thanks Jennifer,
I was in college in the late 70s when sloppy jeans and t shirts were one side of the “in” thing and the preppy look was on the other. I always chose to wear skirts, blouses, tops and dresses that I liked and could afford. The look was more elevated than the sloppy look but not the “I have money look”. I didn’t aim for that. It just wasn’t. I had many comments back then, but I just ignored them and dressed to please myself. I’ve continued to do the same through my life- with consideration for professional, more casual, church, and special occasions. I’ve always dressed for me and that’s what makes me comfortable in whatever I put on.
I’m often the “best dressed” woman in the room (my opinion), especially at work these days. I also wear makeup including lipstick and nail colour. I refuse to dial it down for anyone. This is me. 💜
Thank you so much for this post! I am one of those women who always seems to get the “dressed up” comments even when I’m wearing sweats. I am going to try your strategy suggestions. I want to feel “finished”, visible and confident when I go out into the world, but I also want others to see me as approachable. I think my taupe suede running shoes and casual necklaces will now be getting more wear!
Jennifer, your Monday posts are my favorites. You seem to have found a way to voice what resonates with so many of us. I will always feel more comfortable when I am dressed in an elevated way. Thank you for your words. They really landed today.
Great Post !
My husband and I were at a matinee symphony Sunday afternoon. I was so disappointed and quite surprised to see people dressed like they were at an afternoon baseball game!!!!
Jennifer, you have started 2026 with great self reflection posts. Thank you! I love to dress and present my best self in public. I find folks wearing PJs and slippers out to public places rather appalling. To me it is lack of respect for those around you. I noticed that I receive better treatment and service when I take the time to look pulled together. I bet a stand taller, smile more and look confident. Same goes for some basic make-up.
I enjoy your blog so much! Your perspective, writing & style sense are refreshing! Question: love your lands end quilted jacket – what color is it?
It’s the evening forest green
Many years ago I was asked why I was so dressed up ( by a man in sweats ) at a CYO basketball game. I was wearing chinos and a cotton turtleneck! Whenever I tried to dress to fit in I was always uncomfortable. Now I dress for me and I am more confident and much happier!
I too am in my late 70’s and have had many years of costly wardrobe builds. I always thought it was “fitting in” or dressing classically that was my goal but after many repeated mistakes and no resulting happiness I have given myself permission to enjoy only what makes me feel alive and well dressed. Undergoing final closet purges and finally feeling excited to get dressed everyday and ready for whatever comes, including travel.
That’s fabulous
When did it become okay to wear flannel pajama pants everywhere? I always think that people who dress so “under-dressed” must not have a very good self esteem, no pride in themselves. It doesn’t take anymore effort to pull on a pair of jeans than it does to pull on a pair of pajama pants, it’s still one leg at a time.
Terrific post! I don’t leave the house unless I’m wearing a put-together outfit. That’s just my style choice, it makes me feel good inside and out. I do get the comment “my you’re dressed up,” yet my in-retirement uniform is jeans, a nice top and some sort of completer piece. So be it. When I look around I might be one of the few dressed for the grocery store.😇
I had a friend ask me why I was always dressed up because I wore a necklace and earrings! My husband is the reason for the necklace. When I would ask him how I looked, he’d always say, “you need a necklace.” People are funny.
My husband always says the same thing..add a necklace 🙂