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?
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.