Style Beliefs That Stifle Your Personal Style
For many women our age, style was something that we were taught to approach as a set of rules to be navigated. “Don’t wear color x with color y,” “bags and shoes must match,” “no white after Labor Day,” “women over 40 shouldn’t wear z,” “never mix patterns,” etc. Even if we’ve shaken off most of those (often arbitrary) rules, we may still harbor beliefs that quietly hold us back from wearing what expresses our individual tastes and personality.
There’s nothing inherently wrong with choosing to follow certain style guidelines, but the operative word here is “choosing.” In examining some of our internalized style rules, we might find they no longer serve us. Our bodies change, our lifestyles change, and our tastes evolve over time; it’s OK to let go of what now feels limiting or no longer relevant.
These are a few of the style beliefs I’ve wrestled with over time. Let me know in comments if any of these resonate, or which of your own you’ve let go of.
1. You should always try to look smaller/thinner (or avoid looking larger)
I don’t know about you, but this was one of the most deeply ingrained for me, and one I’ve struggled with most. Underlying the idea that smaller = better or more attractive is the premise that women shouldn’t take up space, should be small, quiet, unthreatening. If you prefer sleek silhouettes, that’s fine, go for it! But I’ve actually gained more style confidence by setting aside this rule and wearing what delights me.
(The flip side of this coin is “I must dress to show off my figure.” If that makes you feel more confident, great! But it’s not a requirement, and as one Instagrammer recently put it, “my body is the least interesting thing about me.”)
My sizes: Shirt – 6, Jeans – Petite 8
2. I need to look different every day
This was one of my mother’s major bugaboos. “You’ve worn that to school twice already this week, you should change.” And I can’t count the number of times I heard her say “I can’t wear that dress again…they’ve seen me in it!” I don’t know whether this is a uniquely American attitude that has roots in poverty shaming, but I’ve noticed it coming from women from all economic levels.
Subscribing to this belief not only can lead to overconsumption, but can be an actual hinderance to developing personal style. We may find our closets are overstuffed with pieces we rarely (or never) wear. Or conversely, we avoid anything distinctive, and fall back on bland, generic clothing that won’t garner attention.
I’m not suggesting that personal style has to rely on a fixed uniform, but there’s nothing wrong with repeating outfits you love. The middle ground between a uniform and style incoherence is building a cohesive wardrobe of pieces that can be worn in multiple combinations, and that always feel like you.
A helpful next step: The Outfit Based Method to Create a Capsule Wardrobe
3. “Every woman needs these pieces in her wardrobe.”
I used to get suckered by this one, and spent years trying to find the perfect “crisp white shirt” and “classic trench.” (TL;DR…neither ever worked because they didn’t suit my style.)
Each person’s basics will vary depending on their lifestyle, climate, and preferences. Buying a particular piece will not automatically make you more stylish. Rather than subscribing to someone else’s “must-have” list, look at the items you wear most, and focus on those.
My sizes: Cardigan – Small, Trousers – 8
4. Saving your favorite pieces for “someday”
I’ve also fallen into the mindset of not wanting to wear things I really love if there’s nothing special on the calendar. Certain pieces stayed in the closet, waiting for the right occasion, the right version of me, or the right moment, some vague “someday” that never quite arrived.
This belief often masquerades as practicality (“I don’t want to ruin it”) or restraint (“I’ll save this for something special”), but underneath it is the idea that our everyday lives aren’t worthy of our best things. That there will be a future version of life that deserves them more than the one we’re living now.
My grandmother used to say, “there’s no point in having nice things if you don’t use them.” What finally shifted things for me was realizing that clothes don’t fulfill their purpose hanging untouched in a closet. They’re meant to be worn, enjoyed, and lived in. And more often than not, wearing a favorite piece, on an ordinary day, and for no particular reason, elevates the day itself.
Of course, not every item needs to be worn all the time. But if something in your closet makes you feel especially good, confident, or like yourself, maybe today is the occasion it’s been waiting for.
Letting go of these beliefs doesn’t mean abandoning all structure or suddenly dressing in ways that don’t feel like you. It simply means questioning the quiet assumptions that shape our choices without our noticing. Personal style isn’t about getting it “right,” or following the correct rules for our age, body, or lifestyle. It’s about giving ourselves permission to wear what feels authentic, enjoyable, and alive—right now, not someday.
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Mine are not wearing white after Labor Day and not repeating outfits. The white thing may have made sense when I lived in the northeast because winter can be messy there (dirty slush etc), but now I live in Florida and still struggle with it. I’ve managed to feel comfortable in ecru year round so I go with that, but white shorts and pants won’t come out til April or May. The outfit repeat thing is ridiculous and yet I always think about what I wore last time I saw the person I’m meeting. I seriously doubt anyone cares if I’m wearing the same shirt. They’re probably too busy thinking about what they’re wearing!
Number 1: I was as skinny as a bone, so that rule never entered my life. Trying to achieve an attractive hourglass figure did though but I let go of that about 20 years ago.
Never 2: Guilty of that, but that’s my own ego and vanity. Plus, I get easily bored with clothes. Now that I don’t see the same people every day anymore, I do wear the same outfit sometimes two days in a row.
Number 3: I never fell for that. Always looked whether it would suit my body and taste.
Number 4: That applied when I grew up and we did not have much money. As soon as I was on my own feet (at 18), I abandoned that rule. I often am asked whether I am going to a party later in the day haha. My reply is: “Every day I am healthy and happy is a party day”.
Greetje
Susan, this article really resonated with me. For years I have been following a lot of those stupid rules and in the last five years I’ve begun to ask myself “why”? (I just turned 70 so that may be part of it!) My thirty something daughter started it with the thought about women appearing smaller and more unthreatening. I had never thought about that before. And as a career person I always shed my “good” work clothes the minute I got home to preserve them. And habits are hard to break. But after following you I began rethinking why I “save” my favorites and why do I think I need to lose 10 pounds when I am healthy as I am.
I think the transition began when I had my colors done by House of Colour. Suddenly realized that black doesn’t do me any favors! Even though my work wardrobe was 70% black. Now my closet is what I like, not necessarily what is in style but in colors that flatter me and make me feel so good.
I must say you handle commenters with grace when they criticize barrel leg pants or browns verses blacks, etc. Each of us gets to decide what we wear each day and I love how you applaud that. And have encouraged us to open our horizons to new choices. Thank you! 👏👏👏
Great insights and I have fallen prey to all of them, esp. #1. And I’m trying to be over them! I’ll add: you can be stylish OR comfy -wrong! Comfort is non-negotiable. And also you have to wear the “in”’color. Sorry, no, I’m wearing MY colors. So you won’t see my winter self in brown! I want to know who is ironing those all of those perfect white button downs anyway…
The ‘saving best’ is something I consistently struggle with. In some cases, I think it’s justified to preserve special items for special events. In other cases, it’s a lifestyle choice: I don’t need to garden in a silk shirt. I have a number of nicer sweaters, though, that I need to promote to everyday wear. I’m also wearing my ‘good jeans’ daily now. They’ll eventually look worn, but that’s the point, wearing and enjoying what I’ve purchased.
I really enjoy your comments. The article today about style beliefs really applies to me. I will give myself permission to wear those items I keep saving for someday. BTW it should apply to jewelry as well. I keep waiting to wear nicer pieces. I live in Florida, and women walking their dog(s) seem to be wearing every diamond they own. LOL. I don’t have a dog so I’m ok there.
Guilty of all of these! Being of a certain age, some fashion rules just become ingrained.
My husband bought me a lovely sweater with horizontal stripes because he really liked it. I took it back beca use I can not wear horizontal stripes!
Ah this is great Susan. I grew up in Southern California (Long Beach) in a wonderful Cape Cod style house right on the beach. So my forever default is a pair of jeans, flip flops and a tee shirt or oversized shirt.I was definitely schooled on looking thin (this was mostly my aunt) and the jeans were only allowed at home–we couldn’t wear pants to school and my parents wouldn’t let me wear jeans to movies downtown. As much as I love style and clothing, I can’t bear to wear too much stuff: bracelets; sweaters over the shoulders; sleeves that billow and get in the way. As a result my look tends to be ‘minimal’ or pared down but this seems to be the way I feel most comfortable. You have certainly encouraged me to branch out and try barrel jeans and lantern pants–they feel very sculptural. They add interest without the ‘faff’. I also love the color combinations that you’ve been coming up with although I still seem to be rooted in neutrals.
My mom had no interest in anything but comfort and an occasional pretty color. She taught me nothing about dressing and apologized for years for not realizing that teenaged girls needed bras and slips. I learned by looking because I loved fashion and color and style and fabrics and…. I heard from others about style “rules” but pretty much developed whatever style sense I have by observing others, looking at magazines, and looking in the mirror. Not a bad way to learn!
I’ve dressed in my current style for years, updating it along the way as styles change – for example instead of slim cut jeans, wider versions. Now I want to move in a different direction that is more sophisticated and elegant, but still fit in where we live. I’ll be getting a color analysis and am looking for inspiration before I buy anything new. I read somewhere that women of a certain age should avoid styles that are prim, preppy, girlish or cute. That’s a rule but it feels right to me. I want my style and clothing to reflect the woman I am today with all the years of life and experience I have had.
This was perfect. Thank you!
Very attractive and inspiring.
Hello Susan! Thank you, from the bottom of my heart for stating rule #1, “You should always try to look smaller/thinner (or avoid looking larger)”. As a plus size 61 year old woman I was SO tired of hearing this rule. It was difficult to hear being younger, but now that I’m gray and older it felt like a double whammy. “Old AND fat” (a clothing industry plague). Over the last year I decided, NO MORE! I’m going to dress for me and unapologetically take up all the space I want. I’m going to dress in color, and wear what makes me genuinely happy! At times it can be challenging finding things I like in my size, but it’s so worth it! I now have clothes I love, that make me happy and confident (something my gray clothes weren’t doing). Once I started wearing color, I was surprised to find I got more compliments than I did when I lived in black & white. Thank you again Susan for reminding ALL women that they are beautiful and worthy in EVERY way!!
As another over 60 plus size woman who struggles to find clothes in bright colors, I’d love to hear what brands or stores you’ve had good luck with!
Hi Wendy! I’d love to share with you the stores I shop at. Like I mentioned, it does take some time, but if I’m patient and don’t try to find everything at one place, I been able to collect a wardrobe of just what I need. For great blouses, I’ve had good luck with Lane Bryant. For jeans (which is what I usually wear), I have great success at Talbots for skinny jeans, girlfriend and trouser jeans. Sweaters, I’ve found Target to be a reliable source this winter along with Quince (online store).
I also like to occasionally shop at Nordstrom or Nordstrom Rack, Amazon and Old Navy.
Wendy, I hope this helps you. Let me know how it works out for you. We gals gotta stick together 😉
My ‘go to’ for happy colorful clothing is Boden. I exclusively shop them on-line and always find something terrific! Their dresses are well made, and many are lined. For size reference, I’m 5’3 and 175 lbs. with a 43″ bust…short waisted, long legs. I’m an ‘autumn’ and dress myself for the endorphin rush that a beautiful, deliberate outfit gives me. I had my colors ‘done’ ten years ago – it’s a game changer! Resent challenge is revamping my shoe arsenal. Plantar Fasciitis took flats out of my life – enter low wedges and lug soles. I’m 62 and living my best life!
I love the colors and patterns at Boden, but I’m about twenty pounds heavier than you at the same height. I think I might be able to fit their tops, but hesitate to order online and have to go through the whole return aggravation if it doesn’t fit. Nordstrom carries a few Boden items and I could return locally….I might give that a try.
Thanks Mary!
This is such a fantastic article! It totally resonates as though you were speaking directly to me. I do have a particular style it seems, that does not often fit the area in which I live. Although I shouldn’t need anyone’s permission to ‘do me’ I do thank you for your advice. I’m claiming it.
Rule 1 – I’m petite, so I don’t really follow this, but I do take caution not to wear voluminous clothing, as it swallow s me alive.
Rule 2 – I eat the same breakfast (and sometimes lunch and dinner) every day, so clothing on repeat is not a big deal to me.
Rule 3 – Many of the “must-have’s” don’t appeal to me, but I did try to force myself into this rule for a season of my life. Needless to say, those clothes hung and collected dust. Then got donated. Live and learn. 🙂
Rule 4 – I did that!!! For SO long!!! Until I realized that my nice pieces should be worn and enjoyed. So, I wear them and enjoy them. My closet is a sartorial toolbox, not a museum!
Susan, you are an excellent writer, why not write a book?!
I lived my whole work life in uniforms..military ones or ones suitable for a hospital setting as an RN. I divided my small wardrobe into three categories then and the third one was ‘not at work’…pretty rudimentary for sure!! Now as a retired older woman I enjoy capsule dressing and I so appreciate your site! I like jeans and tops/sweaters/scarves which are mostly from J Crew. The ‘only for good’ items are small and , yes..they would be taken out and worn..my bad! thank you for this post. Donnie
Susan, a brilliant post, as usual! I have been style-conscious since my early twenties–I had my colors done as soon as I graduated college and was starting to purchase “career clothes”, and it has served me beautifully since. For the past 58 years structured clothing with a defined waist has looked best on me; these days I prefer softer lines in my clothes because of menobelly. I am finding it challenging to figure out what I want to wear with the conflicting “am I too old for this?” and “ugh, this feels frumpy/I don’t feel like me” conversations rolling around in my head. But I love clothes, I love the challenge, and I am grateful for thoughtful, thought-provoking, wise counsel from women like you! Thanks for the time and energy you put into your posts. They are so helpful.
This was helpful and very refreshing! Thank you.
What an insightful post! For me, the corollary to the “saving things for an occasion” rule is finding it difficult to get rid of pieces that are “nice” — objectively pretty, well made, maybe expensive — even if they don’t really suit me or my life anymore.
This blog did give pause for thought. Right now the only one I follow is saving my best. I have ruined so many clothes by not following this rule. Then when I actually need a nice outfit it doesn’t look nice anymore nor feel special. But I am a super messy person who does messy things day to day.
Wow! What a great post. At 68 I’m going through most of these things and am slowly letting go and enjoying my body and clothes! Thank you for this post!
I love your posts, Susan–always thought provoking and timely. I see rules/guidelines in a more positive light because it helps me stay in the game. Too much choice can be overwhelming, and I can easily skew towards frumpiness when I am not paying attention.
Thank you for this sensibly sound message. I need to toss aside certain of these archaic ideas. I’m with you- if it makes you feel confident and comfortable happy, wear it! Often.
I love your reflective pieces Susan and indeed it was a piece on Rethinking Classic a long time ago that brought me to your blog.
Ive let go of most of the habits on your list but one I still wrestle with is trying to look thinner, I’m not huge at all but I know that a fair bit of my style thinking goes j to disguising the tyre round my middle.
How comfortable are those Vince Jelly slides ? Are you able to do much walking in them?
Hi Michelle, they’re quite comfortable and easy to walk in. When the weather’s warmer, I wear them out to run errands, walk the dog, etc.
Hi Susan
I linked to one of your older “style” posts for the very reason you stated. I believe it is so much more about what looks good on one’s body than style. You hit the nail on the head. I have a pair of barrel jeans that I like from Madewell. The barrel is less exaggerated. They are growing on me!!
Thanks, cindy!
I always appreciate your insights into fashion. Many of your picks are a bit pricy for my budget, but I usually can find options that are similar in my price range. I never worried about these rules when I was growing up. My mother was an excellent seamstress who made all of my clothes. We spent hours together picking out patterns and then fabrics to make those patterns a reflection of my taste and my personality. It was hard for me to start buying clothing off the rack after my Mom died. I am now a senior citizen (I’m 77) but I still march to my own drummer when it comes to fashion and I buy what I like. Rules have their place in life, gut rigid fashion rules have never made much sense to me.