Musing If Style Rules Are Stealing Your Joy
Last Monday, I shared two women whose outfits quietly spoke volumes about their personal style. Neither look was trend-driven, and both women seemed to be dressing entirely for themselves, which is always refreshing to see.
It got me thinking about how often we stop dressing that way ourselves. So many of us begin with a sense of curiosity about style, but somewhere along the way, the joy starts to drain out. We’re handed tools like color palettes, body type charts, and wardrobe formulas, and while those can absolutely be helpful, they often come with quiet rules tucked inside. Rules we slowly start to follow without even realizing it.
At first, they promise ease. But over time, they can limit the very freedom that makes style feel personal.
I’ve certainly felt it. Maybe you have too, that moment when you reach for something you love, only to put it back because it doesn’t “flatter” or “fit your palette” or “work for your proportions.” We start dressing for safety instead of delight. To get it right instead of to feel like ourselves.
That’s the trap of formula dressing. Even when the advice is well-meaning, it can end up policing our instincts. And the irony? Some of the outfits we feel best in don’t follow any of the so-called rules at all. Take, for example, me, wearing red.
I’ve never worn red because the color has more energy than I’m usually prepared to deal with, and it tends to overpower my softer coloring. It’s not in my palette, and it’s never felt like “me.” I’m also petite, and technically, wide-leg pants aren’t supposed to be my friend. But last week, we were heading out to dinner and I was feeling exhausted. On a whim, I borrowed my daughter’s red jumpsuit, just to see if it might lift my energy. It did. And it felt fabulous.
To balance the boldness, I grounded the red with my Eileen Fisher black cardigan, Talbots handbag, and Kohl’s sandals. It softened the intensity just enough, but the energy was still there. The color, the wide legs, the movement…none of it followed the so-called rules for my coloring or proportions. But it felt good and sometimes, that’s the only thing that matters.
Try This Instead
If you’ve been dressing by habit or by someone else’s rules, consider trying one of these small shifts this week. Not as a makeover, but as an experiment in delight:
- Reach for something you love but haven’t worn because it “breaks a rule.” Put it on. Walk around the house. See what it brings up. Bonus points for leaving the house wearing it.
- Choose with curiosity. When you open your closet, ask yourself, what do I feel drawn to today? Not what’s most flattering. Not what goes with everything. Just… what calls to you?
- Notice your inner script. If you catch yourself thinking, I can’t wear that anymore, gently ask: says who? And is it still true?
I had to return the red jumpsuit 😉 but this has taught me to loosen the grip I’ve allowed seasonal color palettes to have on my wardrobe.
Here’s a bit more red that caught my eye:
Is there something in your closet you’ve been avoiding…not because you dislike it, but because you’ve been told you shouldn’t wear it?
Love the outfit, specifically the jumpsuit. I never would have chosen anything like that (too young), but now I want to give it a try. Thanks for reminding us to think outside our box.
You styled that red nicely with the black layer to keep the color from reflecting onto your face and “over-blushing” you.
Terrific advice. You look wonderful in this photo.
A lot of us are unsure about what to wear or are looking for ideas about what to wear, but there is so much conflicting advice that after a while, you just have to try things out and decide for yourself – prints v. no prints, what kind of jeans are in or out, chunky jewelry v. dainty, long hair v. short, belts v. no belts ever – the different views should tip us off that maybe there is no one way that works for all, there are surprises along the way, and in the end, it’s just clothes, although we want to not waste money or feel bad about our choices. Also, are we handing off our happiness to what someone else says won’t work for us? So much to think about! One of the biggest boosts to an outfit is confidence – look at how we sometimes laugh at the clothing on runway models, but they walk like even what appears crazy to us is perfectly wonderful, almost like the emperor’s new clothes! I believe it was Audrey Hepburn who said, “A happy girl is a pretty girl” – she was right.
Jennifer,
I love, love, love the red on you. You look fabulous….
Also, your hair is perfect, a great length for you and love
Your sweet smile.
You’re so kind, thanks!
You look fabulous in red! Great outfit and your hair is beautiful! You brought a favorite song to mind “Lady in Red” by Christ de Burgh! Stunning. I love red but haven’t been wearing it as much lately. Have to get back to it. I’ve loved your musings lately, great topics. We’ve been busy with guests so I haven’t had much time to comment, but love what you’ve been sharing. Thank you!
I’m so glad you’ve been enjoying the conversations! Get back to your red, Deby 🙂
Such a freeing and honest post today! You look smashing in this outfit~and the fact that you felt energized and great wearing it~wonderful! Thanks for the red inspiration.
My 82nd birthday is next month and I love red! You look lovely in it! At my age, I don’t have time to be reminded of what and what not to wear. Remember, ladies, most trends and comments are made by much younger people in the design and trend industry. I want to be nicely dressed and not look like I just fell out of a dumpster! But, as you said, Jennifer, wear what speaks to you. Color is good for us. I’ve always referred to it as a “self care” color. 😊❤️
I love your comment and your wisdom Ruth! Have a fabulous birthday, you rock!
Wow. This is a wonderful post and I really needed it. I have bought all sorts of summer clothes this year based on “latest styles” and they just hang in my closet. I do KNOW what I like and what is comfortable and good looking on me but I got way off track somehow. I needed to read this and give myself a talking to about wearing what is right and good for ME. You do look absolutely terrific in that red and black outfit, by the way!
I love the red! You should consider wearing more color…
Robin S
This is the 2nd time I’ve responded to a post to tell you that you look fabulous in (that shade of) red. It doesn’t overwhelm you one bit and it sets off your hair and face beautifully. The lipstick is perfect too.
Hedi
The first time must have been that one red sweater I bought on sale and only wore once! 🙂
Yes to this!! You look fabulous in that color! You truly are an inspiration. 🙂
Red is my fav color and I wear it often & I always drive a red car.
By nature, I am not a rule follower so I have never paid attention to fashion rules. This does NOT mean I am showing up at the opera in casual attire or at a casual event in a cocktail dress. This does NOT mean I’d ever show up wearing something inappropriate. This DOES mean I am not wearing, for ex, wide-leg jeans or nude shoes no matter how popular they may be because they are NOT me.
I dress for myself and often wear blues and reds because they make me feel more energetic and happier. I imagine everyone in my dreaded dentist’s office reaches for sunglasses when I come in. I often dress to lift my spirits, and it works!
LOL, that’s so funny and fun!
That outfit looks terrific on you! Every part of it looks perfect. In the picture, the red looks subtle, which may be why it is right on you. Love every part of this!
I’ll echo what others have said – wow you look fabulous in this outfit!! It’s perfect and so fun!
I rarely wear red but I added a few pieces this summer and love them (def not in my seasonal color lol)
I loved your message today! To be frank I’m tired of the seasonal palettes dictating what we should or shouldn’t wear. It’s an 80s trend that should have stayed in the 80s 😉 Or use it as a tool, but break that rule if we feel like it
You do look amazing in that outfit! Red lifts my spirits too.
I felt so energized wearing it
Jennifer get that red jumpsuit back stat! You look fabulous!
LOL, I will have to order one
I love this thank you Jennifer. I did what you said and looked in my closet and a blue floral maxi dress l save for best occasions called me this Monday. I have this “hang up” of saving best clothes for occasions so then they don’t get worn enough, but today l thought l’m going do it. Feeling very pretty and stylish now l am going to call a friend and see if you wants to go to lunch lol !! You look lovely in red !!
I think many of us have that same tendency but we need to treat every day like the special occaision it is.
First, how lucky for you to be able to share clothes with your daughter! I totally understand the feeling of being overwhelmed by certain colors. You looked great in the red jumpsuit suit. I’m glad it gave you the lift you needed on your night out.
I once did an experiment. I bought two scarves at a charity sale. One scarf was “my colors” and was the sensible choice. The other scarf was a beautiful birds and flowers motif and sparked joy. The 2nd scarf was the one that got worn. We need to spark more joy and worry less about rules!
I love this, Lily!
Good morning Jennifer. You look amazing in red…I think it has pink undertones, maybe that’s why that red works for you. I remember jumpsuits way back in the 80’s. They really pulled you together, same as a wrap dress. I’m trying to add some color to my wardrobe instead of my trusty white and black palate…. Have a great week…
It does have a cool base. Happy Monday!
My coloring is just like yours and I’m 5’1” and 135 lbs. so wide leg pants should look bad but they don’t. I even bought a vertical stripe gauze top and wide leg matching pants from Old Navy and it is so comfortable and cool in this heat. It is my favorite fabric and outfit! My mother loved red on her little white haired daughter so she dressed me in red fussy dresses until I was about four and refused to wear it. I have had an intense dislike of red ever since. So it is a personal dislike not a rules that bother me. I have always listened to my own drum beat as my mother used to say. You look great in your daughter’s jumpsuit!
This was a very interesting post. I too feel a bit trapped by my rules. Some body type…dark on top, V neck, and colours, but others like no maxi or midi or I don’t wear pants in the summer are restricting and darn right cold some days.
But I have to say if I do stick to my rules, I do feel good in what I am wearing.
This led me to thinking what rules do you try to follow…. Another post idea? Oh and red is my colour but don’t wear it much as I feel like I am flashing light but Interestingly when I wear fuchsia I don’t feel the same. 🤷🏻♀️ ….you looked great in your red!
That’s an interesting observation about fuchsia vs red for you
You look fabulous in red!
I always avoided brown because I was told it was not my color (I’m a “winter,” very pale with blue eyes and dark hair). And warm browns with yellow or orange tones don’t tend to look good on me to my own eye. But when the chocolate browns and “mocha mousse” began to trend, I realized that many of them were cooler browns. They may not be as flattering to me as jade green or cranberry, but they look fine, and I’m enjoy the change of pace and feeling in style. I was sticking to pants, skirts, accessories, etc, but I just ordered a chocolate-brown barn jacket for fall!
I think a change can feel invigorating.
As Kathleen above said, it’s time to wear the sleeveless even if our arms are not toned. I decided to do the same last year. At 71, who am I trying to impress? I also started wearing maxi dresses because they make me feel feminine, plus I like the swish.
I love red! It makes me feel energized, strong, and happy. Wear the red Jennifer!
I do love the swish too. It’s just fun
Just saying-I think you look great in red! That was a WOW outfit:).
The red jumpsuit looks amazing on you!!! Thank you for reminding us to stay true to ourselves.
Hi Jennifer…
I am a new reader and enjoy your prospective and your words of kindness! Unfortunately, the judgemental words of others are so not necessary and I’m hoping you can scroll right past them. I live by the words “if you have nothing nice to say, don’t say anything at all”! Keep the joy in your heart as you share your blog…I’ll be reading each one!
Love that red on you! I bought a pair of ponte knit pants in red at the beginning of summer because I loved the colour. As I drove home, I was second guessing the purchase but thought I’d look through my wardrobe and see if I had anything that worked with red. To my delight, those pants look great with silver shoes and light grey knits. I hadn’t thought that a warm/cool combo would work. Thanks for bringing your style musings to us each week!
That sounds like a very fun color combo
Brava!! Questioning the rules is the first step to increasing our joy.
It’s taken me 50 years to figure this out, but it’s been so freeing.
XOXO
Jodie
Good for you! We should all wear what makes us happy. I love red and wear slot of it in the winter. In the summer it is bright pink. But today I have soft colors on and enjoying them. Have a wonderful day!!
The red does look wonderful on you and the tied cropped sweater is perfect with it. I bought a short red jacket a few weeks ago after completely removing all red from my wardrobe over the past ten years or so, since I let my hair grow out and go white. I can’t wait for cooler weather to wear it. Red was once one of my favorite colors and adds such cheer to a wardrobe.
A red jacket sounds so fun!
You look fabulous Jennifer. That red looks like a pink red on my screen, which actually was in the Summer pallet back in the 4 season PCA.
Enjoy the long weekend – I’m on my way to the golf course.
You’re right and I think that’s why it made me feel so happy. It didn’t clash with my undertone. Have fun at golf!
Jennifer thank you for your deep dive. Your rules rant 😂 made me realize I actually don’t allow “do’s and don’ts” rules to dictate my closet. Just struggle with personal proportions, 5’ 3” and color. (Your guidance on proportion and my recent color analysis helps.)
The “wake-up” was my years long struggle with skinny jeans and finally gave up. Never did find a skinny that flattered my fluffy athletic body. (Wish I had that chunk of change back. $$$)
I also think you look great in the red jumpsuit. It’s a fun outfit with energy.
That’s one of your cutest outfits, Jennifer, and is so flattering! As for me, my palette calls for cool colors. My closet is full of turquoise, teal, raspberry, black, and grey. I love those shades, but my favorite color is green. The cooler greens often don’t appeal to me, but I do love some of the warmer tones. Just recently I decided to add a few of those “no-no” shades of green to my wardrobe, and I love them! At my age (78) I figure I can wear whatever I want. Thanks for your wonderful blog posts. I never miss a one.
We have earned the right to wear whatever we want. Happy Monday Judy
My color palette includes corals and watermelon, but I thought now that I’ve “aged” a bit, I should go for softer versions of those colors, but your article has inspired me to lean back into those bolder shades.
The jumpsuit looks fabulous on you. I love red. I always feel happy when I wear it. I’m not sure if it even looks good on me, I just like it. I am going to look in my closet and pick out something that I love! Thanks for challenging us 😉
yay!
I have never subscribed to the color theory. I know it makes things easier for those who need rules, but it’s so restricting. I wear what I like. If I were diagnosed as whatever purple is, I would be miserable. I hate that color. If someone told me I had to wear it, I would stay home naked for the rest of my life. If some color doesn’t “look good” on me according to some chart, then I guess I will not “look good” while I wear it.
You need to buy that red jumpsuit! It looks fabulous on you!! I liked your comment about dressing for joy; it’s kind of my mantra. Because I live in warm climates most of the year, I can dress in bright colors and patterns that are simply fun. As I age, I realize that I don’t have to follow convention regarding how an older woman dresses. I dress for me and what makes me happy!
This looks great on you. You’ve just given us the perfect reason to always be open to a little change. We may not know what we are missing!
I too dislike red on myself and only maybe wear in during Christmas. However any other time I wear red I usually take it off!
Until we moved to Nebraska I never wore red. In Nebraska red is a favorite color, and not just at football games. Now, I love red and wear it often. It is energizing and youthful. You look great in red and should add it in your rotation. Break some rules!
How fun!
Love the boldness of the red—. Ladies we can put on any color we want to wear and make a fabulous statement!! Do it!!
I love the red jumpsuit on you! The whole outfit a full WIN! I recently stepped out of my comfort zone and bought some brightly, printed breezy palazzo pants. I love wearing those pants. It is still a little “scary” when I wear them😃 but I feel so chic when I wear them.
A palazzo pant is so fun to walk in. I love the swish!
Great article! I have a closet full of stuff, but also find myself second guessing the items. Almost 70, so it’s, is it trying too hard – yeah seriously a loose cable vneck and dark jeans. I plan to spend time this week putting together some outfits I feel great in, and donating the items that are just not. Have a blessed week! Dress to make yourself happy!
You look great in the red jumpsuit! I’ve found that sometimes when I don’t follow my colors, and wear something that I like, the feedback from others convinces me that some colors don’t work for me. I used to have a pumpkin shirtdress, loved the color, but every time I wore it, people kept asking me if I was getting enough rest, that I looked tired. So I went back to respecting the color rules. I do still wear pumpkin, but only as part of a print with colors that do work for me. And some colors that I think don’t work, do work and I get good feedback from others.
That looks a nice soft shade of red maybe because is reducing the intensity of the colour
Yes, and I left space between it and my comlexion.
I think that you look fabulous in your daughter’s jumpsuit!
I will respectfully disagree about red not being in your palette. I have read about your multiple adventures with color analysis. I believe you have been analyzed as a summer or a cool, soft, light in the Your Color Style system, which I find to be the most accurate of all the systems I have seen. I believe there is a red for everyone! Yours is a cool, softer red. The photos you posted sure look like the red in your daughter’s jumpsuit hits the sweet spot :).
I also think the wide legs of the jumpsuit look great. They are flowy and do not overwhelm you. In fact, they balance out your broad shoulders.
I hope your daughter does not mourn the loss of her jumpsuit too much (wink, wink).
I love your advice today.
The red outfit looks terrific on you!
The red outfit looks amazing on you! I too have always felt that I could never wear red. Now I am curious to try it out.
I think that red looks great on you! I too have stopped wearing red, although I can’t really say why. That’s a nice cool red too, which helps your coloring and gives you life and energy. Wear it again! Or buy one like it.!
Lol, I’ll have to buy one like it. Maybe I should be looking for red sweaters based on the season.
That looks absolutely lovely!
Hello from Winnipeg!
You look fabulous in that red jumpsuit!
Lately I too, have been drawn to red items and agree with you on the way some “rules” block us from wearing what we are drawn to!
Thanks for your encouragement to be ourselves!
Happy Monday Karen!
Amen! You look darling!
Great read. It has set my inspiration higher for dressing this week. You look absolutely beautiful in your jumper outfit! Thank you and cheers to dressing for joy! Jennifer in Port Angeles
I love where you live. Great town!
I agree with you. I wear denim b/c I love it and can combine it with many other clothes. Wearing something I feel good in can transform my day. I teach Silver Sneakers exercise classes so when I get out of these clothes, I want to wear something I really enjoy, which, now is gauze in hot summers in Louisiana. I feel like you have given us permission to wear what feels comfortable, fun to us!
There’s a huge value in wearing things that feel fun.
Good Morning Jennifer. Great article. And you look absolutely fabulous in that red jump suit. Just wondering, did you have to have that hemmed? I’m also 5’4. Maybe I just haven’t had enough coffee yet, but not seeing where Quince indicates inseam.
I didn’t have to hem it but my sandals do have a low, stable wedge which adds a bit of height.
I love that jumpsuit so much I had to take a look. It has a 27” inseam which will be perfect for me at 5’4” .
You look fabulous! What a stunning outfit! Red is my favorite color but I rarely wear it anymore. You have inspired me to take another look at why and how I can still wear my favorite color!
If it’s your favorite color, go for it!
Wow how wonderful to see you in color and your hair looks great please temper the bland with more color I would put that photo in my dressing room as a reminder of how color is joyful and mood changing.
Amy
F
LOL, I am already shopping for more color to play with.
Your article is so timely. I recently purchased a light blue, short (flutter) sleeve casual dress from Land’s End. I’ve ALWAYS been self conscious about my arms, but decided to GET OVER IT. I love the dress and will wear it with confidence!
I’ll be 70 in November. Well past time to wear what speaks to me.
Happy Birthday Kathleen!
It’s nice to see you in some color and that is a perfect shade of cherry red! I used to wear red a lot but it seems to be overpowering now with my mostly white hair. Perhaps I just need to find the right red. Love the whole look!!
Yes, and play with how you style it. Perhaps with a bit of space between it and your complexion.
J the red jumpsuit is smashing on you…..tremendously youthful. Big YES ❤️
I felt fabulous in it! It was so fun too.
Simply stated, you are amazing and draw out the best in all of us. Thank you
That’s so sweet. Thank you for being here.
Jennifer, you look fabulous and happy in this outfit! I think you should wear red more often. I love wearing red; it is always uplifting to me.
Wow….that red jumpsuit looks fabulous on you. It reminds me of some of your past conversations when you’re traveling south of the border and you felt you needed something more colorful. I don’t wear red a lot, but do like it when i do wear red. I also like turquoise with red as an accent option in warmer weather seasons.
That sounds like a great combo. I’ve always loved turquoise but don’t own any.
This article resonates! All the “rules” especially related to color palettes are exhausting. Wear what you like.
Wow, Jennifer! This is one of my favorite things I have seen you wear. Feeling good in what we wear affects how we appear to others, rules aside. I always enjoy your posts.
In my VERY humble opinion you should include more red in your wardrobe! This outfit looks fabulous on you. If I had worn it, the only thing I would have changed would be the black shoes. I would have gone with a neutral/nude color to take away the weight from the bottom of the wide legs. Either way, it’s a great look!
Good morning Jennifer! Last week I was so taken by the descriptions of the two women you saw that I decided to continue purging my closet with that simplicity in mind. I thought about how amazing it would be to walk into my closet and choose what to wear from my new “minimalist” collection of clothing! Fast forward to yesterday when I came home from shopping, with an outfit in my bag. I rarely shop for a complete outfit because I buy pieces that work with other items in my closet. This outfit included an embroidered denim jacket, wide leg jeans and a tank top. Not one piece is what I “should” wear. The colors have never been in my adult wardrobe before and the busy embroidery and beads are way too much. When I tried it on it made me smile and on top of that each piece felt good on. This morning I looked at it and wondered “what I was thinking”? No, I’m not taking it back! I’m going to wear it and smile some more. It feels a bit freeing. 😁
YAY! Enjoy it!
Jennifer, I love the red on you. It’s encouraged me to try something daring.
Love your blog.
Mary
Yes to this!! I am pear shaped and a little fluffy. I have avoided white pants/shorts/skirts for years even though I have them and love the look. I recently started wearing my white skort and have received many compliments and most of all, it feels like me!!
Awesome!
When I opened the email and saw your red jumpsuit my first reaction was, Wow, she looks great in that outfit. Color, style, everything worked. If this is breaking any rules, it’s inspiring.
Happy Monday!
I love your articles and how authentic down to earth you come across in your expression of personal style.
Some of your articles are so practical such as the on sleep and more recent on preparing for a loved one’s surgery , so thank you 🙏🏻 I look forward to reading more !
Happy Monday Barbara!
You look young and energised! The mirror and how you feel is sometimes the best fashion rule to follow. 💃
You look real nice in red but I still like your hair a little shorter like in the video that did.
This outfit looks adorable on you! I fall into this trap all the time. I am going to pick an outfit that “calls” me today! Thank you!
This outfit looks so cute and youthful on you. Im going to take your advice and try something different!
I needed your message this morning, Jennifer. Thank you. After a lifetime of believing my coloring was that of a “summer” type, an analysis showed I was a “”spring” type. It was disappointing to learn that some beloved items apparently didn’t love me back! Prior to your post, I decided to keep and wear them anyway. After your post, I feel better.
Yay!
Wow Jennifer! Your hair looks amazing and thick. This outfit really suits you well and maybe outside your comfort zone but you deserve to have experiment. You have earned it to shake up your look. I love your style for sure.