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?
Jennifer, enjoyed your post today. I recently wore an animal print zip-up jacket to church and was told I was so dressed up! Don’t know if it was the jacket, animal print, or both?! I said thank you and it’s warm. I Iive in AZ where anything goes!
Bravo Pat, great reply
This is an amazing article! Your advice is spot on. Thank you.
Susan Henry
I get this comment, I just laugh and say, “ I always dress like this “. Then I quickly give them a compliment on something they have on. This seems to disarm them.
I realize they have made an inappropriate comment , so I give them the opportunity to think about their actions.
If it happens amongst my friends or peers, I may have to make choices about who I want to engage with in my life.
A true friend lifts you up.
So true!!
The answer to ‘Why are you dressed up?” is, “What, this old thing?” Or is it?
The serious answer to any remark is “Thank You.”
If you tell the thrift store beginnings or the age of a garment that was complimented, that throws doubt on the person who complimented you.
Thank you covers it nicely
Thank you Jennifer for affirming my thoughts exactly about my dressing every day. I dress very similar to you. I do live in casual cowboy country in rural mountain Colorado but I don’t own a single cowboy outfit or item. I love wearing a column of color and that tends to read dressed up even with my white sneakers on for walking the dog. At 81, I’ve learned to always please myself in what I wear as I love clothes. I also tend to live in jeans except for the hot summers here. Then I wear flowy linen pants which read dressed up. I just say thank you, I’m very comfortable.
This post was so interesting to me and I appreciated the hints of how to dial down the dressy in our wardrobe if we want to. I find as I get older, that I’m less concerned if I am dressier or more casual than others around me, although at times I still try to “fit in.” My husband has two business trips that I go with him to each year, and last year, both times I wore inappropriate shoes for the occasion (the shoes were comfortable, but not as comfortable as they needed to be for power-walking to and from dinner with the much younger group!). This year, I am wearing what I know to be extremely walkable shoes (but not sneakers) and I’m not going to be concerned if I’m dressed up as fancy as some of the others who can still walk blister-free in heels for many blocks! Not me anymore! LOL! Speaking of comfy shoes and tricky feet (yours and mine), check out The Walking Company for lots of good supportive shoes. There’s a combo sneaker-boot style that keeps popping up in my emails that might be comfortable for you now. I’d love to see a post on styles from their website that you’ve found both stylish and comfortable. Thanks!
I don’t remember ever being asked why I was so dressed up. I have had someone ask if I’m going to hoe the garden. If I’m leaving the house, I try to dress for the occasion. I don’t really agonize over that. Am I presentable? Do I like what I’m wearing? If I’m staying home, comfort is the goal. Anyone who drops by unannounced takes his chances. I laugh at the “finished hem” remark you make because a much-hyped designer specializes in “unfinished,” and I have avoided that designer because I already have outfits suitable for garden hoeing.
Excellent post. We should dress for ourselves. As for going to a “nice” restaurant and many patrons are dressed like they went to Home Depot, shame on them. Often my hubby and I look “overdressed” but we think we are just being respectful. Never stop dressing in what makes YOU comfortable.
Hi Jennifer, This is a great topic. I often have people say I’m dressed up when I all I did was add a scarf and cardigan over a top. I always have earrings on too. For me, it’s usually about the weatheras to the scarf and cardigan. I had a brief hospital stay last year and after I wore essentially the same black cardigan, scarf and graphic tee for weeks, with black yoga pants. Even my home nurse commented. It seems a scarf is some kind of magic accessory! Love your blog, as always! At our age let’s just dress the way we want in what makes us feel good. 🙂
Brenda
Agreed
I loved this post . Looking put together is not a bad thing! One of the best compliments I’ve ever received was from a colleague at work who told me I always look put together. It’s exactly what I was looking for. I don’t dressed ‘fancy’ for work, but I do put effort into looking put together!
What a great way to start the week! Your post this morning was right on the money! Thank you Jennifer. I shall try & carry it in my head each day I get dressed!
Regards
Nancy
I love this Monday Musing and all of the comments. I have to confess that I devolved into being a slob during a long period of grief and loss. It’s so easy to wear sweats when that is the norm in one’s area. Lately, I feel like I’ve gone through a fashion 12 Step program to get back to dressing in a way that makes me happy. When I was younger, I often wore feminine outfits – breaking the ugly man-suit dress-for-success rules. A job recruiter once told me that I should cut my hair short and wear man-suits in order to look less attractive. I wasn’t a great beauty, but I did my best to make the most of what nature gave me. I said no thank you for the position he was looking to fill – I wasn’t going to make myself look generic to fit in. Now my way of dressing is to rebel against the trend of dressing like toddlers in jammies. (People wearing flannel pajama bottoms in public is one of my pet peeves). Jennifer – I love your guidance on elevated 3rd layers and accessorizing. I’m even applying these rules for my basic dude-in-jeans husband (who as an engineer, never had to dress up for work). He likes wearing a nice jacket and occasional cashmere scarf when we have date nights.
Loved your article. My dad always said “if you dress like a clown you’ll be treated like a clown”. I am 71 years old. I have noticed if I dress up a bit I am treated well compared to when I rush out the door in my house clothes on a quick errand. Also, would never show up to a restaurant with white tablecloths looking dressed down, it is a respect to the restaurant owner to arrive well dressed.
Thanks Jennifer ! Love your articles !
Absolutely!
All I have to do is wear a dress to get the “dressed up”comment. When I shop with a friend and they admire something “dressy” but won’t consider it because “Where would I wear it?” My reply is ” To the grocery store or shopping or anywhere else that you go.”If I have something I like I find a way to wear it.
Go Judy!!
I really enjoy and feel myself when I put on a casual dress or skirt yet I sometimes see people stare at me in the manner you would look at a purple cow. It used to bother me but I am dressing for me now.
Fabulous Yvonne
Jennifer,
I just love your articles! It is so uplifting each day to read your posts and see your classy style, dressy or casual. So glad that I have this to look forward to forward to each day. Thank you.
Happy Monday. I’m glad you’re part of this community of fabulous women
I really like that look. Gave me a chance to see that Quince sweater and pants in action. You looked the perfect dressed casually style. i say forget what others say. You do you.
Loved today’s post immensely. I’ve always loved getting dressed up, just like my mom and grandma. But none of my sisters got the get dressed up gene and I struggle with their endless casual and sweatshirt vibe, jeans or stretch pants even when going out for dinner. Love them to death, but I have resisted the urge to dress down for their comfort. I have the core wardrobe and great mix of jackets for layering and basics and only occasionally need to add a piece or two, but still struggle with styling and jewelry coordination. Trying to balance the pear shape has been a lifelong never ending task. Appreciate when you incorporate those body shapes in your comments. Thank you.
Keep resisting that impulse and dress to please yourself.
I have always dressed for the day either by the “mood I feel that day” or my specific plans are for the day…but never by what I think other expect of me. I have always lived by the theory that I would rather be overdressed and look put together than be underdressed. That’s just my personal style. It has served me well for many years! 🙂
I dress pretty intentionally and I often get comments usually positive, even in the grocery store. Last night we were at a very high end restaurant and I did wrestle with with what to wear. I knew I would wear black dress slacks, metallic ballet flats and I hoped to wear my Christmas present off the shoulder white sweater. The sweater is a little daring and has sparkles on it. Would it be too dressy? And how and what jewelry? I decided the pearl and diamond necklace was too much so I let the sweater do the talking there and wore my black pearl dangle earrings. Topped it off with a cashmere vibrant magenta shawl for warmth. I may have been a little overdressed for our group but I got complements.
Your outfit sounds fabulous. The compliments are a great signal.