Personal Style File: Rethinking “Flattering”

Every year about this time, I go back and re-read what I think is one of the best posts I’ve ever read on a blog: You Don’t Have To Be Pretty. (From Erin at A Dress A Day.) I especially love the line,

Prettiness is not a rent you pay for occupying a space marked “female”.

It’s a great reminder that we don’t owe “prettiness” to the world. Or sexiness, cheerfulness, thinness, attractiveness, vivaciousness…or any of those “-nesses” that so often get piled on women as cultural expectations. Of course those are all dandy things to express, if we feel like it. But we are not obligated.

I’ve been thinking about how I still sometimes hold myself back from trying or wearing certain things because they aren’t “flattering” (i.e. don’t make me look taller and thinner). Many years ago when we were on a vacation in Puerto Vallarta, le Monsieur was reading the book “Who Moved My Cheese,” and was very inspired by the concept, “what would you do if you weren’t afraid?” The next day he went parasailing (he’s terrified of heights). He said he’s glad he did it, but doesn’t feel the need to repeat the adventure. 😉 I relay that story, because lately the phrase that’s been repeating in my brain is “what would you wear if you weren’t afraid?”

Style Inspiration

Which brings me to the outfits in the image above. (Source) I spotted these the other day while scrolling through Pinterest, and they really struck a chord for me. I’ve always been drawn to Japanese style and aesthetics, exemplified by simple pieces in beautiful fabrics, unfussy-but-interesting shapes and textures. Ease and harmony.

Like the dramatically shaped jacket I posted a few days ago, they offered a signpost of sorts, or “style clarity point” helping to bring into focus my style direction.

I’ve had a hard time breaking away from the long-over-lean silhouette that has been a reliably flattering one for me. But it’s also felt too restrictive of late. Yes, that outfit on the right could be styled with slim pants, but it’s precisely the texture, fullness, and ease that attracted me, and IMO makes the look more interesting. Wearing short sleeves is something else I’ve avoided in recent years. But in doing so I’ve passed up a lot of interesting tops that I (otherwise) really liked.

I should stop here and say, there’s nothing wrong with choosing clothing that we find flattering or that gives us confidence. But where I take issue is first with the very narrow definition of “flattering” that many of us have internalized. And second, with the idea that we are somehow transgressing if we flout the rules of what’s “flattering” when choosing what to wear.

Personal Style Affirmations

What if we were to expand the definition of “flattering” to include “that which makes us feel joyful and authentic?”

Here’s what I tell myself: you don’t owe it to the world to look taller and thinner. You don’t owe it to the world to look younger or more conventionally attractive. You only owe it to yourself to be authentic, to wear what feels right. (Which may be different tomorrow than it was yesterday.)

Getting Back To Basics

Have you overcome any fears of wearing particular styles that otherwise appealed to you? Where do you usually find your style inspiration?

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88 Comments

  1. The two outfits at the top really appeal to me, too. Working from home, I have gotten into a rut of wearing the same thing, usually choosing the scrungiest items in order to “save” better ones for when I go out in public. I do dress up to go to town.
    I get my inspiration partly online, from blogs, Pinterest and Instagram, and partly from real women on the street, whom I can see moving. I admire those who stride confidently, and that requires clothing that isn’t restrictive and sensible shoes.
    To h*** with pretty. I prefer “interesting,” “confident,” “competent,” “artsy,” “intellectual,” even “eccentric.”

    1. Artsy intellectual; – c’est moi!
      And I would buy a number of things from HumanWomen if I could read Japanese.

  2. great post thank you. its good to be reminded that trying to be attractive isnt our reason for being on the planet

  3. i wore a denim jumpsuit to work the other day….it may or may not be flattering, for some reason that’s never been the most important thing for me…but as a 55 YO who works with alot of 20somethings, i was scared to wear it, in fact, it took me over 2 weeks to actually wear it…but i loved it and finally told myself either i wear it or it needed to get returned that day….so wear it it did, and i got a lot of compliements!

  4. I love the idea of dressing for you! I am 55 years old and just now starting to figure out what I love wearing.
    I have been asking myself if the item “gives me joy”. Some items are beautiful only to me….. and that is perfectly OK! They make me smile …….

    1. I love this. When I first read Marie Kondo’s book I thought “sparking joy” was kind of corny TBH. But over time, I’ve realized she is dead on. And it works in all areas of life, including our clothing.

      1. another comment on Marie Kondo’s book that helped me – “downgrading to “loungewear” is taboo”…the ratty old sweaters and tees are donated and I have a few lounging outfits that “spark joy” and honor my down-time.

        1. I do keep some worn and stained garments for the kind of housecleaning and gardening that can destroy clothing in terms of making it decent for street wear. Not vacuuming, dusting or doing dishes or washing, but getting down on knees or using a mop when bleach or other harsh substances are involved. I can’t afford to destroy decent garments.

  5. What a wonderful post today. So much of it resonates with me, from the Japanese aesthetic to the sleeveless tops and wider pants. Like so many 60-something women I know, I’ve been stuck in the skinny jeans/leggings with tunic tops mode. I am not overweight, yet I still feel I have to conceal my wider hips — and even if it’s over 90 degrees outside, I am ashamed to show my bare arms in a sleeveless top. Of course, I should know better, but I am caught in the same trap you write about. I think everything I wear has to be flattering — or has to hide “flaws.”

    I’ve even purchased those flowing, wide-leg pants (from Eileen Fisher or Artful Home) but then I don’t have the courage to wear them because I wonder if I look frumpy in the wider, baggy cut … so I switch the wide-leg pants for black leggings. Funny thing is, I think the wider pants look artful and elegant on other women. But I am starting to change my mind about this, and thanks to posts like yours, I am seeing the wisdom in embracing my own style.

    I’ve also been reading Thomas Moore’s book, “Ageless Soul,” in which he talks about how difficult it is in our culture to age joyfully, and to grow older with a sense of purpose and acceptance. When we keep trying so hard to look perfect or young, he says, we miss out on the benefits of aging well. Your post today is another affirmation of that.

    1. Go ahead and wear the wide leg pants! I bought a pair of Eileen Fisher wide leg pants on sale at the end of last summer, thinking it was the front end of a new look. I just wore them for the first time on a Florida vacation. Love them! I feel comfortable and confident. No one to please but me.

  6. Now, THAT is a phrase to remember:

    “…the phrase that’s been repeating in my brain is “what would you wear if you weren’t afraid?”

    A new montra….

  7. I think of myself as an arty type, but not too “out there.” There is a timelessness to being a creative no matter how you define yourself. I shop boutiques for the styles that I can’t find in chains. And have always found Eileen Fisher pieces can fit in this category. Look at what Judi Dench wears. Her clothes suit her body and she has her own style, which I very much relate to. It’s what feels like me.

  8. I feel you are experiencing the normal evolution we encounter in our sixties. I loved the phrase “the narrow definition of flattering that many of us have internalized”. This is more than just being freed from what our corporate image might have demanded, but how we choose to spend our time and efforts. I am into the last year of my sixties, rocking my silver hair and choosing to put as much time into my health and well being as my image. Enjoy the ride.

  9. I will repeat the old ( but true) words my mother said to me:
    ” You wear the clothes, the clothes don’t wear you.”
    That points to CONFIDENCE in yourself whatever you choose to wear.
    If you don’t feel confident in your choice, leave it in the closet.
    Excellent post that many, many women of a certain age need to read and consider when dressing.

  10. I have been reading Timeless Beauty by Carla Mathis, and one of the revelations are the many pages devoted to body specifics (short neck, wide hips, etc.) — so half the page is about how to emphasize, and half the page is how to conceal it! (Because time and place, culture and desire influence whether you see a trait as beautiful or not.) After spending a lifetime trying to de-emphasize large hips and rear, I realized some (like JLo) actually try to emphasize them because culturally, that’s desirable. It has quite turned my head upside down!
    Your post also resonates with me because, as I have attempted to update my style, I have found a family split in what they believe is flattering to me in terms of color and silhouette — my white family vs. my husband and his Japanese American family. The differences are rather large and unreconcilable! So, I have decided that I will ultimately have to please myself, and not put off my spouse too much, either. 🙂

  11. Great post. There are a few things I love to wear that aren’t all that flattering, including some linen pants that are cool and comfy but not my most flattering. I’m packing for warm weather today and needed to read this. Thanks!

  12. KUDOS TO YOU, SUSAN! One of your best articles! Two years ago, I started wearing sleeveless tops and dresses(I live in Phoenix)….it’s exactly what you said in your article….dress to bring yourself Joy! Thank you

  13. Thank you! With my full hourglass figure, I am advised to wear waist emphasizing clothing. I don’t always want to do that! My latest purchase is a large-scale black and white gingham check (rather straight) knee length dress from Jjill that I’ll wear with capri leggings. I feel it is congruent with my newly pixied hair and my sunny personality. I don’t always want to emphasize my va va va voom! My favorite summer look is Judi Dench from Best Exotic Marigold hotel. Long cotton or linen top over wide (cool and airy) ankle length pants. Beautiful scarf–interesting earrings and I’m cool and comfortable. Thanks for that affirmation!

  14. This is a wonderful post. I love the outfits you show, and the Pretty post even more. Thanks for sharing this journey in your thinking, it resonates with me too.

  15. Thank you for a lovely post that will be a help to me as I prepare to spring-clean my wardrobe. I enjoy your posts very much.

  16. I’ve found a couple of treasures lately at our hospice thrift store. It’s a great way to try a color or a style without investing a lot of money.

    1. Absolutely, Leslie! I saw an ombre yellow scarf, NWT, at Goodwill that I loved! For $1.99 I was able to try a color I had avoided.

  17. When I’m in a fitting room with some potential purchases, I play this game…I put the garment on without looking in the mirror and see how it “feels”…that’s the first test – then I open my eyes and see if it makes me smile – “spark joy”, I guess – I’ll probably buy it. But, currently, I’m on a mission to wear what’s in my closet without shopping…I have a well curated closet with pieces I LOVE – thanks in great part to reading your blog for the last 7 years – and am inspired by YOU, Susan. Thanks you for these very thoughtful posts.

  18. They only thing I’m afraid of is looking like I’m trying to look too young. Some of the styles I favor tend to skew more youthful, but I like to think I put my own spin on them. Case in point: I purchased a pair of Dr. Martens within the last few months. The first time I wore them, it was with a Talbots cardigan :).

    1. Tomorrow I’m going to fetch a third pair of Doc Martens Winona mary janes – on deep discount. I’m wearing my black ones as I write. These are textile – like running shoes but much more supportive, and have that funky timeless vibe. But the ones I’m picking up are cherry red!

      I found a nice summer skirt by Prana in a dark denim colour, with pockets. A-line, for the bicycle and not too short.

      Kimberly, I also don’t want to look in costume. When I was in my 20s I wore such things as a vintage flapper dress found in a trunk, but I’d look daft doing that decades older. I’m very much a boho and always will be.

  19. Thank you for this post, Susan! I really needed to hear this!! Have been spending so much time and effort trying to find the “perfect look”… as if anyone really cares what I look like! Much better to enjoy what we wear and not feel constructed by all of the rules and expectations that are seen almost as cultural mandates! I will re-read your post and try to fully absorb it and live it

  20. This post could not be more timely and relevant for me! I’ve recently moved away from the long over lean silhouette. In part, it was because I’m tired of it but in much larger part, it was because I finally realized that the main reason by far that I was dressing that way was to cover my bottom half, about which I’ve always been very self conscious. So almost my entire wardrobe was based on hiding something. When I look back, I’m saddened that I spent so much effort trying to conceal my perceived flaws on a daily basis.

    The catalyst for this change was my discovery of Eileen Fisher slouchy pants. The minute I put them on I knew I would be making a profound change in the way I dressed. I felt comfortable and confident in these pants, and not the least bit self conscious. It felt miraculous at the time:). In addition to Eileen Fisher, I’ve found that FLAX linen pants are wonderful (esp the Floods and Ankle Pants) and also that MUJI has a small line of women’s tops that play nicely with slouchy/less fitted pants.

  21. Love all of these, particularly the blue blouse with the short sleeves. Would wear this if I didn’t have wrinkly upper arms and batwings! But wait, hey I don’t have to be pretty!! I’m going to look for that blouse and buy it! Thank you for this post – you made my day. I’m going to start dressing for ME not what I think someone else will like.

  22. First, you are such an intuitive writer who is able to verbalize what many of us think but don’t even realize it. So thank you for giving words to my thoughts! Several times when shopping for a specific event, I have Inlisted the help of a personal shopper. I recall her bringing me things i enjoyed looking at but would never choose for myself. I recall how much I liked her suggestions and the compliments I received when I wore them. Those 2 outfits you show are beautiful and to me a specific style that I like but prolly would not try. But, hey, why not? We should all learn from this post and take a leap,of faith and try something that may feel different for us. As they say, life is short! Eat the dessert first, wear the bright color, go parasailing! (Well maybe not parasailing) ‍♀️

  23. Thank you for this. Sometimes all the fashion blogs I read seem so shallow – all that effort, and it all seems to be about making more money for the clothing, makeup and jewelry companies. But it SHOULD be about empowering women (and men) to be confident, to stand up for themselves to get what they deserve, and to ENJOY life – we only get one! All the work and effort I have put into losing 30 pounds in the last 2 years, money spent on clothes and time spent on makeup and choosing outfits – gives me joy as I go throughout my day feeling as happy with my outside as I always have with my inside. Well-said, and full of great quotes.

  24. This is a great post – the type of post for which I love this blog the most. It’s especially appropriate today – International Women’s Day. Here is one thing I really dislike. Whenever someone posts a photo of someone on Facebook – say, a daughter or son or even oneself – most people’s comment is “beautiful” or “gorgeous,” as though that’s the best compliment they can pay someone. Admittedly, if the picture is just of the person, with no context, there is not much else to say. In a case like that, I usually say “nice picture” or something like that. Just my two cents,

    1. Just before reading this post, I ‘loved’ a photo of my young niece wearing a full skirted dress, cowboy boots, and a huge smile. Yet I hesitated to type the usual comment about how pretty she looked, so your words, and those of Susan’s and her readers, are really making me think. No more of that! I’ll focus on descriptions more important than superficial appearance.

  25. This is one of your most empowering and important posts! Thank you! The outfits posted, although not ones I would choose for myself, would tell me there is an interesting person inside them. I tend to run very hot and so have had to embrace sleeveless tops and exposing the old lady arms for much of the year. I have become rather tender towards these arms and other similar ones I see around me! I mostly dress to please myself and feel good in my clothes sensually. In other words, feeling hot or constricted is not happening. I do think it is important to not retreat to invisibility however and there are many ways to let your clothing speak up. I like some color and artistic expression in addition to the feeling good factor.

  26. Very good article! I will be repeating this phrase, over and over. I like the outfits, I can feel the quality, ease and simplicity in them. What would I wear… actually… dresses. Why? They are easy, fit me better than pants, and have movement. I wore them all summer last year, and yep, I had some joy!

  27. Today is International Women’s Day!
    “prettiness is not a rent you pay for occupying a space marked “female” “ is an excellent discussion point for IWD. Today is a day, but should be everyday, that females get the recognition and support for their accomplishments and for striving to succeed. Prettiness means different things to different people…prettiness of face, prettiness of actions, prettiness of mind. I think the other quote, “what would you do if you weren’t afraid?” “, really epitomizes International Women’s Day and Susan’s blog for today. It has been, is presently, and will be those women who aren’t afraid who make the difference and make the world a better place. Take a look at the quotes on the Google site today.

  28. Susan, a clothing line was I personally love is Niche. It is a women owned company out of San Antonio, Texas. Their artful designs and colors are so inspiring for when you want to feel great.

  29. I’ve been pondering your post all morning…the idea that I don’t owe it to the world to be “conventionally attractive”. What I’m wondering is, do we owe it to our husbands or SOs? I have this vague thought in the back of my brain that if I am ever husbandless my hair would be shorter, makeup would be less and my clothes more interesting/weird/comfortable (I can’t decide on the word). Even though I don’t think he has an expedition of me evidently I have one of myself. Lots to consider!
    But please, lead the way with these new silhouettes and show us how!

    1. Susan, I would encourage you to do what makes you feel great. If you feel like you are”in a rut” it might be time for a change. Initially, your husband may think this is unusual however, if you are happy with the change your whole body will reflect this happiness. Grooming ourselves to please others is never a good criteria for doing what we do.

  30. My key to wearing a scarf like a French woman was realizing that however a French woman wears a scarf is “French.” The key is not the styling — it’s the confidence with which you wear it. (Now I need to apply that to a wonderful cashmere poncho that I can’t wear without feeling like “Look at me, I’m wearing a poncho!”)

  31. I think the thing is that when we rely on formulaic dressing we can get too predictable. When someone says to me, “that looks just like you” I find myself thinking — I’m in a rut.
    At this stage in my life I’m dressing to please myself, and it’s not like I want to look short and chubby, but sometimes it’s worth at least trying something else on.

  32. Thank you so much for your wonderful blog. I doubt you will ever know how much you inspire and encourage us to enjoy our lives – to feel better about ourselves everyday, enjoy getting out and about either locally or long distance travel, to remain curious. I really really love the question “what would you do if you weren’t afraid.”

  33. This is definitely one of your best posts! It says so much about what image we choose to express
    ourselves as individuals. Unfortunately, I think fashion has a lot of rules for women of a certain age! When we step outside of what is expected we can be accused of trying to act too young. As if its somehow threatening to younger people for us to wear their clothes! We are struggling with not becoming invisible and yet we have such narrow options according to some fashion experts. I love many of the things you said in this post and I hope it will inspire me to try new things and add some fun (joy) to my closet!

      1. Exactly! That’s my point. No styles should be considered taboo to anyone based on age. The only thing limiting us should be the weather.

  34. Does all of this mean I can wear my denim jacket with jeans? Pretty is such a vain concept. When a fashion blogger posts endless photos of herself and all the comments are mutually fawning it is not interesting or informative.

  35. Your post hit so many nails on their heads! But what I found uplifting were all of the life and age affirming comments from amazing women. At 79 I will never wear sleeveless anything again but I feel myself drawn to a newer easier way of dressing. The Asian aesthetic is very appealing and, despite the big eyes I will likely get, at least initially, from my kids, I am asking myself “if not now, when”. For the last 45 years I have dealt with alopecia and had to learn the lesson that I am not my hair. This switch in wardrobe should be a piece of cake. Rock on ladies.

    1. Lee, I have seen 80 year old women topless on the beaches in France; please go sleeveless if you feel like it!

  36. Love this post and all the comments! “Authenticity” is the new “Pretty”. So appropriate for International Women’s Day!

  37. This was an important post. I think a lot of people will find it meaningful. My own, admittedly eccentric,mom taught me to only dress for myself and to wear what made me feel happy in my clothes. As I got older, I have really embraced that, but for those who have trouble with it, there is a lot here that could be freeing. Hope so!

  38. Hi Susan, I’ve been reading your blog for a while now. I have enjoyed your content and I do think you have fab personal style. I have to say this is the best post from a blogger aimed at this age group that i’ve read – thank you!
    What I’ve found is that wearing clothes you love is emotive and it’s those feelings that give you pleasure and confidence. Life’s experiences when you do look back are remembered through emotions eg the ticket stub to a show you went to, the first card you husband wrote you etc That’s how powerful our emotions are. So when you dress the way that makes you happy you are affected by those feelings and it shows to others. So on those days when you wear what you truly enjoy wearing, others probably notice a difference. It’s not fully the clothes that people compliment you on, it’s also about your vibe. Check yourself out, you’ll be smiling more and standing straighter too on 1 of those days.

  39. Thank you for this post today. Your comment of “what would you do if you weren’t afraid?” really resonated with me as I am finding that retirement seems to be making my world smaller (if only in my mind). I think I should feel that retirement is more freeing so I have been asking myself that question all day. I read the book “who moved my cheese” way back when in my working career. It was mandatory reading at that time and I wish I had kept that book! Again – terrific post – and I so enjoy your blog!

  40. YES. I’m so tired of “flattering,” as if the only acceptable thing is to hide any part of your body that isn’t immediately acceptable to the very narrow and nearly impossible beauty standards. I’m 5’2″. I’m never going to be tall, and I don’t need to look tall. The singer Lizzo talks about realizing how the body you live in is the only one you have, and you have it today–if you don’t love what it looks like TODAY (without any weight loss or magic potions or surgeries or botox), you are wasting your own time. Here’s to embracing what is and being fearless about it!

  41. Love this post. Is it okay with you if I share the first paragraph as a quote on my social media? I, of course would credit you, your blog and the blog you reference. I just love the message and would love to share it. If not, I completely understand.

  42. Fantastic post, I’ve been coming to the same idea recently. After years of advice on what overweight women should and shouldn’t wear I now see more images of curvy women rocking their own, and varied, style. I’m enjoying the freedom to choose what I wear based on something other than ‘does this hide me?’

  43. I have only one caveat to add that was not mentioned above. I think that proportion is so important with these styles so that they do not overwhelm. I think many of them look great on taller women and unless they are cut to fit the body of the wearer, even if they look great on the website and the concept pleases our eyes, they may not be the best unless properly altered or fit off the rack.

  44. I dress as I want to every day.Very occasionally I let the situation influence what I’m going to wear,like for a meeting or something. However, most days when I get dressed, I dress only to please myself and meet the demands of temperature. I am lucky enough to be able to buy what makes me happy, this ranges from mostly vintage,some repro, to boho styled stuff and often quite costume-y. It may make people stare,but it(to borrow a phrase)sparks joy in my soul. I realize that this may be partially a result of my generation where, other than school dress codes, I have never been discouraged from wearing whatever floats my boat. I don’t dress for anyone else,ever. Sometimes other people like what I’m wearing too,which is fine. I like to think that what I wear flatters me in some sense, shape, color, what have you, but some days I know it’s not cute, then it’s jolie-laide,and it makes me happy too.It probably helps that I have a variety of very eccentric friends so our normal is not everyone’s cup of tea, but it works for us. 🙂

  45. Susan, I so enjoyed reading your thought process and the conclusion you’ve come to. I think we are so trained to do anything to look taller and thinner and like you say, look at all we’re missing out on! There’s a designer I met here in Sonoma and dresses in lots of volume and interesting fabrics (mostly linen, you’d love it) and she dresses that way because it’s interesting to her! She displayed her clothes at a retreat I sponsored last year for image consultants. Hardly anyone tried anything on. I just don’t think they could see beyond the fullness. It’s like we’re allergic to anything that makes us look bigger than we are even if it’s dramatic or simply wonderful. I hope you keep talking about this, Susan. It’s so necessary to expand our fashion minds.

  46. Such a wonderful, right on article! It’s so hard to refocus our eyes when fashion changes dramatically.
    It’s so funny that you mentioned the Japanese esthetic. When I was there years ago, feeling all frumpy and gawky being so much taller and bigger than any other women there, I got more complements. I felt very uncomfortable being the center of so much attention. I had a very nice chat with our Japanese interpretor. She explained that Japanese women so much admired my “beauty” as I am very fair skinned with reddish hair and a volumpuous body, pretty much the opposite of a Japanese woman. My point being, body type and style are very much a cultural thing.

  47. Oh my! “We don’t owe prettiness to the world.” This is powerful and totally apropos for International Women’s Day and every day! I needed to hear this, even at age 61.

  48. I have to wonder how often French women have this dilemma, of wondering throughout the course of their lives, as their body shapes shift (not that they shift all that much unless you’re overdoing carbs) whether the clothes they like or love are no longer flattering. Maybe this does go through their minds. But I have lived on and off in Europe for years now, and it’s pretty clear to me that Americans are the only group of people who just don’t get the kind of sartorial training that many (not all; there are some egregious missteps in many places in the world) Europeans do. I’d say it’s hard to feel pretty or whatever it is you decide you want to feel if you aren’t aware of your dimensions and how your clothes fit. I personally had the great good fortune of growing up in countries where there were no clothes for me ‘off the rack,’ and all of my clothes, including my uniforms, were tailor or seamstress made to suit me. Flattering is ephemeral if your goal is to hold on to the same clothes forever, by the way, unless you’re able or willing to invest in tailoring. Your body changes, your skin color changes, your ‘eye’ changes… you are tired of a “look” and want something new. It’s pretty clear that one’s style *must* change and evolve, as long as blood is pumping through your veins. This doesn’t mean ‘fast fashion,’ it just means a certain amount of realistic adaptability to who you are now and whether or not your clothes reflect that reality. I suspect that means, for a lot of women, giving up the look they/we hold in our heads of how we once looked or how we ‘should’ look, and seeing what’s actually there rather that some sense of ourselves we hold only in memory.

  49. I have never hesitated to wear sleeveless and short sleeved items in spite of not being slim. I would love to see you branch out in your fashion photos in clothing you describe in this post. Long over lean is a wonderful style, but I know I would love seeing other options.

  50. What a FANTASTIC article from A Dress a Day. Thank you ! Your post and Erin’s post ( A Dress a Day ) reminds me of The Man Repellar. That has been Leandra’s position since she was a teenager : we don’t owe “pretty” to the world. We owe ourselves what we love and brings US joy. What a wonderful concept !

  51. “You don’t owe it to the world to look taller and thinner. You don’t owe it to the world to look younger or more conventionally attractive. You only owe it to yourself to be authentic, to wear what feels right.” That’s truly profound, Susan! Thank you!

  52. Thank you, this post has certainly given me food for thought. I live in a warm humid climate and I am constantly struggling to find clothing that is flattering and weather-appropriate. But maybe I’m thinking of the trade-offs all wrong!

  53. This was a great post Susan. There are too many rules about what does or doesn’t look good, how to look taller and thinner. Well at barely 5′, I am not going to look tall no matter how hard I try. While I want to look good, which would be my own definition, I think wearing interesting, comfortable clothes is where I am headed. Why have to always dress monotone, or avoid so many great styles because the arms aren’t perfect. I feel that sometimes comments to your blogs are very critical, and appreciate how you respond to this. Please keep doing what you do so well!

  54. I believe this post was in part responsible for my splurging on two brilliantly colored flowy tops yesterday. I’m top heavy and I usually avoid that kind of emphasis, but I loved the way I looked in them. Maybe I will work up to sleeveless!

  55. Great post! At 61 I’m starting to look at outfits in a whole different way. I’m tired of being “afraid”of wearing something out of my comfort zone. I recently wore a wrap and loved it. Small steps but I’m doing it. Feels good.

  56. Thanks, Susan, for putting these thoughts out there. At 48, I am finding myself adopting and loving many things that my mother did not like—what she would have called the Earth Mother. They are long hair, dangling earrings, and less makeup. I suppose it’s my midlife crisis, but it’s great fashion fun!

  57. Thank you for this post- I love it! I have a bunch of ideas in my head about being “appropriate” that I got from my mother and grandmother, as in “appropriate for a 60 year old woman” and often pertaining to dangly earrings for some reason! Sometimes I need to have a stern talking-to those voices from the past! (Said with a tender smile.)

  58. There are so many styles I would like to wear, including the above, but when I try them on I look like I am playing dress up and trying too hard, or I am swamped by them. I watched a video last week which helped explain why as a classic extreme shapes, colours and styles don’t work for me. I’m not comfortable with feeling conspicuous and with my clothes wearing me, so I think I will have to stick with the styles I know suit me whether or not they flatter, or are ‘stylish’.

    1. Hi Lynn, when you say “classic,” are you referring to Kibbe type? (After much back and forth, I’ve decided that I’m a Soft Classic.)

      I get that feeling you’re referring to, and describe it as Someone Else’s Clothes, where I just feel wrong in something, regardless of whether others think it looks good on me.

  59. Great post. I am 68 and I look at young women on IG or blogs who don’t have as their first criteria ‘flattering’ flattering being synonymous with making us look thinner. They wear what they like and more power to them. I don’t wear this because it makes my bust look larger or my hips wider. Marie Kondo has a point. We should only have things around us that ‘spark joy’. We should love what we wear not just because we think we look thinner in it. Like you I love the Japanese aesthetic, but always thing that’s a lot of fabric for me. I need to move away from that and learn to wear what intrigues me and makes me happy.

  60. Good points. Good conversation. Being “chic” is my moto!! Whatever that means Is different for everybody. For me is being healthy, in great shape of frame and mind, a good haircut/ color, manicures, pedicures, well fitting clothes, polished shoes, color, smart, understated make-up, a little stand-out accessory, nothing screaming expensive, perfume, good posture, good attitude! And let’s add CHARM! So lacking these days, but if you treasure yourself, you will most likely feel that way towards everybody you meet!!!! I attest to that!