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?
This post is so true for my life! I no longer feel the need to explain or apologize when someone asks- why are you dressed up? I love your strategic tips on how to make the “dressed up” outfit look polished, but still casual.
Thanks for your post!
Share your joy in responding! I wore a white denim skirt and sandals to a summer reunion (most others had on cropped pants), and the “mean girl” said, ” I haven’t seen anyone wearing skirts anymore!” I told her how much I enjoy cool skirts and pretty sandals, with a smile, of course!
There is always a mean girl in the mix. It helps to know that your style intimidated her. Bravo
I’m a college instructor and find that dressing extremely casually to teach has become more common since the pandemic, but it’s a trend I won’t buy into. I look and feel my best at work when I’m dressed like a professional in polished business or business casual clothing. If anyone says anything, I suggest saying, “I wore this because it made me feel good.”
I also am a college administrator. You are so right. Sometimes you can’t tell the professor from the students. I think it’s really important for the faculty and staff to dress in a more professional manner to provide an example for the students. I don’t mean dressy or suits and ties. Just look like you thought about what to wear and didn’t throw on what you left on the floor by the bed!
It just made my day to hear about the designer who has made his grandmother part of his business and remembering how my grandson arrived at his style. Good thoughts to start the week. I really enjoyed this post and being true to your who you are. Thank you.
Happy Monday
Great post. I always like when people ask why you are all dressed up. I just says thanks. Sometimes you just feel like dressing up a little more. Nothing wrong with that.
If you ever find shoes in a wide width, I’d love to see those. Thanks!
I certainly will. I need them now too.
Last week two strangers at my Pilates studio commented on how “dressed up” I was when I came in to take a class. I was wearing shiny, dark brown Old Navy leggings, a caramel brown, cropped, turtleneck Forever 21 sweatshirt that had a rope tie at the waist, under the sweatshirt I had on a cream and brown-striped long-sleeved tee, on my feet I had $20 caramel brown suede Uggs knock-offs, and I wore my caramel brown Ralph Lauren calf-length wool coat. I consider the coat to be the only “fancy” item I was wearing. When I acted surprised about the women’s comments, one pointed out the dressy coat. I told her the reason I chose to wear it that morning was because it is my longest coat. I wore it to try to stay warm during my drive to the studio in the single digit cold. I also pointed out that almost everything I had on (exceptions being Amazon $20 boots and my coat) came from Goodwill. I told the women that I hate paying retail prices and that Goodwill is my favorite store. I do not think that I was dressed up. I do think that my outfit was well put together. The stripes in my tee shirt, which may or may not have been seen by my commenters, matched my sweatshirt. The sweatshirt and my boots were the same color and my coat was maybe just a little darker. I call it a well put-together outfit because of the colors I chose. The actual pieces were pretty much the same things everyone wears at the Pilates studio – leggings and a tee shirt and/or sweatshirt. I always do co-ordinate my top and leggings colors, so, for example, I don’t wear my olive green leggings with a clashing top. I find it kind of funny that my simple outfit got the reaction it did. It just goes to show that color co-ordination can turn something very simple into a well put-together look. I find it easy to do because I only buy things in a fairly narrow range of colors. I know what colors look best on me and I keep my wardrobe to that palette.
Wonderful outfit! I would have complimented you not asked why you were dressed up. I’m inspired by well dressed women, not intimidated. Bravo
Thanks so much for this Jennifer! I love looking pulled together and sometimes receive comments like “why so dressed up?” or “you look so formal!” or “where are you going?” I am tempted to say “thanks! did you mean to say ‘you look great?!'” … but I resist. I purely try to look nice for myself, and I enjoy fashion — no apologies, no excuses – thank you for reinforcing this with your supportive post.
I was asked this very thing by my dental hygienist. I was wearing ankle pants (Talbots), a poplin button down shirt, a relaxed linen blazer and loafers. I was a little surprised, but told her I just like to look nice when I leave the house, even when running errands. But after noticing everyone around me, I guess her question shouldn’t have surprised me. Let’s just say that people seem to be dressing much more “casually “ than when I was younger. I understand wanting to be comfortable, (I was) but casual is different than sloppy or I don’t care, in my mind anyway.
Wow and thank you. I actually like getting dressed up. But being retired, not many “reasons” to do it. And as you described, have “scaled it back” with prevailing trends. Sometimes too much. I am not afraid of expressing my personal style preferences, but more that I don’t want someone else to think that I look down on their choices. I like and will incorporate your suggestions as to sneakers, quilted jackets and suede loafers, as I have them all in my closets. I think some jeans also qualify and I typically choose mine in a narrow straight leg shape which is most flattering to my small frame and also reads as “classic”. (Since you have mentioned several times in your posts that you wear jeans most days, I wonder if that’s also a way you try to “fit in” e.g. cashmere sweater paired with jeans.) Maybe I need to develop my own “math rule” such as 2 upscale pieces paired with 2 more casual? Something for me to try.
Jeans definitely change the outfit formality. Wash, distressing, and shape all play into it. I have an entire post on jeans for 2026 coming out tomorrow.
This message really hit home for me. Most of my friends tend to dress very casually for every occasion while I like to dress up a bit: nice black pants instead of jeans, a crisp white shirt with a scarf instead of a shapeless top. In other words, I dress in a similar fashion to you! I consciously try to avoid apologizing for my outfit. I can’t control how others dress, but I appreciate those who put some thought into it. Thank you for giving us permission to stop feeling guilty about our efforts to be well dressed. PS: my husband and I were in Paris last fall and were disappointed at how many Parisians now dress as casually as Americans.
That’s interesting. I haven’t been to Paris in several years and anxious to go again.
When I retired, I realized that all my tops went with basic color pants so I invested in jeans, corduroys, shorts and skorts in those same basic colors. Even after 7 years of retirement I still “dress up” everyday. I have always enjoyed looking nice for myself and for my husband. Even when I was working I dressed the same 7 days a week. Why I would I dress up for people at work and not for my husband and family? It doesn’t take any longer to put on a nice pair of pants, shirt and shoes. I feel how you dress shows respect for yourself and others.
Touché Nancy!
I LOVE this post. It hit home with me. I am an almost 78 year old retired technology sales rep turned personal trainer. Since so much of my time is spent in workout clothes, I try to elevate my look. I have received the occasional comment about being “a little elegant” for my surroundings, and I get looks in the gym. I also get comments from women in my age group about being “skinny”. (I’m not!) I just try to smile and take those comments as compliments!
I will usually say “Im not dressed up just comfortable and warm”.
Not an apology per se but something close, right?
I will change my response for sure as I feel good in my clothing choices.
Having heard this all my life, I simply smile and say “thank you ….. I feel great today.” I feel when someone comments on my appearance, they are: expressing their dissatisfaction with their own or are sincerely complementing you on yours. I chose the later and have a nice day. ,
I love that response – I am going to try that!
It’s a perfect response. I agree
Very positive article. I was new at my church and wore a hat, on Palm Sunday, because I have hats, and wanted to wear it before Easter. A lady in church loudly remarked, “I didn’t know we were wearing hats this week” , with the obvious attempt to say I was over dressed. My hat my outfit. I replied every day is hat day! No embarrassment, no apology, they have now learned after 9 years, I have my own fashion standards. Thank you for the affirmation to wear what is you. Have a blessed week.
Everyday is hat day!!
May I ask what size you bought in the Land’s End featherless coat. That color is sold out on line but there are two listed on poshmark and I’m trying to decide what size to get. Normally I like to get medium because this time of year we wear bulkier items under our coats…..but I’m just not sure. Thank you for your help in helping me decide between small or medium. I’m 5’4”, 118 lbs.
I have a small, but if I needed to wear something bulky under it, I would choose a medium.
Yes, people do ask … Isn’t this when you say, ‘what this old sweater?’ LOL?
I really like boots in the winter and don’t feel the need to soften with sneakers. Of course, my Bogs winter boots are yellow rubber — which dial down any formality a lot!
OMG. This is so me! I have “always” heard; “why are you overdressed, you are always so put together”… It has gotten to a point where with my best friend I actually dress “down” to not make her feel uncomfortable. Honestly, I am now retired 6 years and sick of dressing down…it is just not me. Thank you so much for helping me figure out how to tame my polished look. After all, don’t we always want to look our best!
Oh yes, I have experienced the “are you going to work” comment while at a doctor’s appointment. It was meant as a compliment but made me think I was overdressed. You are so right that casual dress is the norm these days. Yet I continue to enjoy putting together interesting and flattering outfits that often elicit comments from friends.
I have too but we shouldn’t let it dim our light or our style.
“Dressing well means dressing to please yourself”. Thank you for that statement! At 71, I pretty much do that, but you are right, it does draw comments and looks. Shouldn’t we get to “be ourselves “? I look forward to your emails and what to me should be common sense. Appreciate you Jennifer.
Thank you! I’m glad you’re part of our community.