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 🙂
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.
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.
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