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?

Stay in touch.

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88 Comments

  1. March 8, 2019 / 5:38 pm

    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.

  2. Susan B
    March 8, 2019 / 6:08 pm

    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.

  3. Carol
    March 8, 2019 / 8:48 pm

    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.

  4. March 8, 2019 / 10:04 pm

    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.

  5. Susan D.
    March 9, 2019 / 8:07 am

    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.

  6. Isa
    March 9, 2019 / 9:16 am

    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 !

  7. March 9, 2019 / 4:43 pm

    “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!

  8. Anna
    March 10, 2019 / 8:45 am

    Nice post, which makes one think. Here’s to experimentation. Still waiting to see Susan in a skirt!

  9. Lisa
    March 10, 2019 / 12:11 pm

    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!

  10. March 10, 2019 / 3:31 pm

    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!

  11. Book Goddess
    March 11, 2019 / 7:41 am

    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!

  12. Karen
    March 11, 2019 / 9:38 am

    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.

  13. Ginger
    March 11, 2019 / 2:31 pm

    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!

  14. Deborah
    March 12, 2019 / 11:19 am

    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.)

  15. Roseann
    March 12, 2019 / 8:27 pm

    This was the best article ever.

  16. Lynn
    March 13, 2019 / 9:26 am

    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’.

    • Susan B
      March 13, 2019 / 9:32 am

      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.

  17. Nancy Karpen
    March 16, 2019 / 5:29 pm

    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.

  18. Daniella
    March 25, 2019 / 4:26 pm

    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!

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