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.