What’s Flattering Got To Do With It?

Source. In my next life I will have her hair. And those shoes…

Flattering. It’s a word we toss around quite a bit. The cut of the jacket is flattering. That color is flattering. Hem length X or Y is most flattering. In general usage, “flattering” could, without stretching too hard, be translated to mean “that which makes the wearer appear closer to the cultural ideal.” In our particular time and culture, this often breaks down to: tall, thin, young, pretty. (Just an observation, not an endorsement!)

While there’s nothing wrong with wanting to look our “best,” when we serve “flattering” above all else, it can squelch our expressive style. Think of many of the women who are considered style icons; at one time or another they broke the rules of what’s considered flattering in order to honor their personal style.

I think that the reason some women can look great in clothing that’s not conventionally flattering isn’t because they’re a size 0 or were born with some recessive Style Gene. I think it’s because they choose items that are an organic expression of themselves. When we dress in a way that’s aligned and integrated with who we are, we create a kind of harmony that comes through even if we’re not following the rules of flattery. Looking at the photo above, would you call this outfit “flattering”? The proportions shorten and widen, yet there’s a gorgeous mix of color and texture, and unexpected shape. I find it pleasing to look at, even though it doesn’t conform to accepted notions of what’s flattering. (We’ll leave aside the practicality consideration for now, as that’s a whole ‘nother discussion!) Some could argue that you see the clothing rather than the woman, and yes there is some of that. But if style is expression, we’re seeing a version of her as she’s chosen to express through her clothes.

We should also consider how a particular style or color or piece of clothing makes us feel when we wear it. While black is probably objectively not my “best” color, I love how I feel in it. I love how I feel in clothing that moves, even though it may sometimes have more volume than is considered optimal for my short stature. I love how I feel in boots, even if they can shorten the look of my legs. Confidence and joy are flattering too in a way that transcends pure physical appearance.

For some of us, personal style does align with what’s most conventionally flattering, or we prioritize flattery in our style choice hierarchy. Again, there’s nothing wrong with that. But if the notion that “it’s not flattering” is keeping you from wearing something you love, perhaps it’s good to let “flattering” take a back seat from time to time. Or perhaps we broaden our definition of “flattering” to include harmonious, aligned, balanced, powerful, a true expression of who we are.

How do you define “flattering?” Are your style choices based primarily on what’s conventionally flattering?  Do you ever let go of that, and if so, what motivates you to do so?

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  1. Really interesting post. Yes I think her look is creative but not flattering and iI can see now that flattering can confine us. I suppose some want to show their creativity through their clothes and others want to opt for a flattering look, even if it tends to be the more generic.

  2. Really interesting post. Yes I think her look is creative but not flattering and iI can see now that flattering can confine us. I suppose some want to show their creativity through their clothes and others want to opt for a flattering look, even if it tends to be the more generic.

  3. Wow. How funny. I have just finished an article (featuring the exact same outfit as 1 of 3) with a related topic (but not flattery) when I saw this image on your facebook page. My article is totally different, yet has the same kind of meaning. On the blog tomorrow 🙂
    Yes this lady looks striking. She stands out. Even though the general advice on my blog is not to wear pants this wide with this length. But ‘rules’ are meant to be broken and this lady has style and looks great. It’s about personality and daring to stand out.

  4. I think flattering means what you have on accents your best features.
    For me personally I need to look as slim and tall as possible for something to flatter me!
    Great post and while I do not feel this young woman is making the best choice of shapes for her figure it works and I do love her hair.

  5. I think it depends on how you define flattering:). The outfit obscures her body, but focuses all kind of attention on her beautiful face and hair. People can be beautiful without following the social conventions on how the female figure ought to look. I believe that’s what you’re saying here, so I’m just chiming in.

  6. Several times, I have abandoned an article of clothing after seeing a photograph of myself in it. While I might have loved the blouse or sweater, once I saw a photo of me in it, I no longer felt comfortable wearing it because of how the camera saw it. I may need to rethink my reaction.

  7. Flattering has always meant it makes me feel and look ‘slimmer’. I have always had a weight problem. But, on the other hand, I don’t feel the need to hide my figure under layers of oversized clothing either. As I age I’ve gotten to the point where I try for a balance of it feels wonderful or it makes me feel great and slimming.
    This woman looks wonderful in her outfit; she has obviously found clothing that appeals to her and makes her feel good.

  8. She looks stinning! Flattering’s such a restricting word. Isn’t it far better to feel great in your clothing and exude confidence rather than be miserable by imposing restraint? xxx

  9. “Confidence and joy are flattering too in a way that transcends pure physical appearance.”
    Brilliant post and so beautifully written! I think you’re right – always being a slave to what is flattering can stamp out creativity of self expression. Creative dressers want to experiment with shape and colour in ways that are not always about making you look like an hourglass or thinner or whatever is preconceived as being flattering.
    I don’t agree with some of the sentiments above that success with experimental looks are confined to the young or striking looking. You only have to go to Ari’s Advanced Style to see proof that actually older women (and not all of them are necessarily striking looking) can totally carry off the avante garde.
    Your post will be an inspiration to me the next time I go to the wardrobe to pick out something to wear.

  10. This is such a fantastic post! Really thoughtful. When I looked at the photo, I immediately thought about self-expression and confidence being an important part of how we look and feel. Whether something is flattering or not, if we love it and it makes us happy then surely that’s more important? I agree with Kathy, in some circumstances flattering can be a criticism.

  11. The word ” flattering ” used, when describing someone´s way of dressing/ wearing clothes, sounds as if a ” fault ” of some kind has been successfully corrected by the ” right ” choice of clothing.
    Right now, I try to dress to my own comfort, to the occasion, to the climate, by choosing rather simple clothes.

  12. Well, it is important to me right now to find clothes that do both…make me FEEL like me and also flatter or fit my curvy shape. I feel better when I know the garment fits me. As a larger, curvy woman, boxy clothes can make me look even LARGER and when I see that, I FEEL bad. It really is just between me and the mirror and has nothing to do with culture. I know what I want to communicate with my wardrobe and a flattering fit on my figure is part of that communication. It’s a personal thing…and should not really involve anyone else. What you wear and what you communicate is up to you and then you will FEEL great! You have seen me in clothes which do not fit…because I love them…but my best looks, like I have on my site today, are the ones which flatter my figure. That look is exactly how I want to FEEL every day.

  13. Flattering is a word I dislike for so many reasons, some of which you’ve mentioned here in your great post. If I’m in a store trying something on, a the salesperson tells me ” Oh, that’s very flattering” on you, I leave. I find it’s an implied criticism and have actually called Neiman Marcus about it.

  14. It’s a novel combination of color and fabric. Who knows if looking at these photos in 30 years she’ll like it as much. Flattering is not only for the viewer, but also for the wearer. It’s been my experience that time is the best judge.

  15. For me it simply means that certain colours and shapes enhance the wearer’s appearance rather than detract from it.

  16. Flattering is like slimming. I remember my grandmothers using those expressions when I was a girl.. It implies that you have some defect that needs to be concealed. The blue and green with the model’s hair are beautiful. At a certain age, we should feel free to express ourselves freely and joyfully. Great post!

  17. You don’t HAVE to be a size zero, of course, but a funky look like this is a lot harder to pull off if you are. The reason she looks great is that she’s not filling out these huge garments. (And I say this as someone who WOULD fill them out)

  18. On the other hand, I have known some large women who look absolutely adorable in the ensembles they choose–especially when the outfit is a bit avant garde. I think some people have a certain fashion sense and others do not. Size is not always the determiner of what flatters and what does not. I do agree that personality and obvious happiness has a lot to do with it.

  19. To quote Mick Jagger “flatter flatter flatter. What does it matter?” I think flattering is whatever makes you and those around you feel good.

  20. I think when you are a young woman, you have a bit more leeway as far as ‘flattering’ clothes go. And also ‘striking’ looking women seem to be able to pull outfits like the above off much more successfully, too.

  21. I admire women like Lynn Yaeger, who break every fashion rule there is but still look completely au courant. I don’t think Isabella Blow’s lobster hat could be considered “flattering” on any level, but it was fashion genius. But I’m a conformist, and would rather not be remembered as the girl with the invertebrate on her head or as the woman in the cookie monster shirt. Good for her though – she makes it work.

  22. When I think “flattering,” I think of clothes that aren’t too tight, don’t gap, or make the wearer pull, tug, or walk uncomfortably because they fit really poorly because they’re too small or so big they don’t stay on the body. Clothes that are avant grade in shape, color, or style I find refreshing and intriguing. I guess it’s a matter of personal confidence: one who cares what THEY think, more than what others do, will go for whatever makes them feel happy and glad to be selective. One who is unsure of herself, or trying to please others or fit into some role or idea of what should be worn, will never look like they’ve made flattering choices. As for the picture? Love her hair, love that sweater (i WANT it!), and the color of the skirt or are they pants is lovely. Loathe the shoes. But I admire her style.

  23. I totally agree with California Girl’s comment! I am over 65 and know that some colours make me look old and haggard, whereas other colours suit me better. So colour-wise I do tend to go for “flattering” colours. However when it comes to styles, I go for what I like. I have an amazing number of striped tops, which I love to wear, even though horizontal stripes aren’t meant to be “flattering” for those of us who are vertically challenged! I wear what makes me feel happy and think that is my best look!

    I do think that the woman in the photo is stunning, but I think it is her attitude that makes her look so good.

  24. I love the outfit the woman is wearing, on her. The colours are beautiful and the black hair and black shoes are perfect bookends for the strong shapes in between. I am happiest when the outfit I’m wearing is both flattering and an expression of me, but sometimes it’s one or the other but not both. If I’m going to wear something that I know is not particularly flattering but I love, I have to be in a very confident frame of mind to carry it off.

  25. It’s a great outfit, I just wish so many women would wear shoes that fit. If your toes extend past the end of the sandal, they don’t.

  26. It’s a great outfit, I just wish so many women would wear shoes that fit. If your toes extend past the end of the sandal, they don’t.

  27. Confidence and joy are flattering, too. Perfectly put! If we can be playful, quirky, confident and joyful in our choices then we will be true to ourselves and happy with our own style. Great post. 😉

  28. “When we dress in a way that’s aligned and integrated with who we are”. This post really challenges me to think about how my clothes, etc. reflect who I am. Since retirement, and a major wardrobe/personal re-assessment, I’m drawn more and more to simple clothing. As I shop around, I feel less and less interested in pattern, quirkiness, anything that makes me feel unsure of myself. I love to see flamboyant looks on others but lack the ability/desire to pull this off myself. The feeling I want is one of comfort, ease and confidence. Thank you for helping me bring this into focus.

  29. I notice “flattering” when used by a salesperson, nearly always means “makes you look thinner”.

    If women pick clothes in which they are “expressing themselves”, there is a tendency of choosing “fun” clothes that make them look like big toys. In an Advanced Style video, these very women say they feel confident and love what they are wearing. So I guess, it is up to each woman but as LauraH says, I am drawn to the simple and well-made.

  30. Excellent writing and discussion of the concept of ‘flattering.’ I agree that feeling good and enjoying self expression are more important factors than dressing to conform to a norm that is defined outside of self. The photo above is very appealing to me! Self exploration, at this point in my life, is highly valued.

  31. Without confidence and joy nothing you wear will ever look “flattering”! After all is said and done as you so eloquently pointed you have to feel good about what you’re wearing in order to “sell it”. Sure, there are basic guidelines, but they can’t be successful without your enthusiasm as the most important accessory.

    Spashionista (Alicia)

  32. Excellent post, Une Femme. As Style Crone said above, at this stage of life I know what flatters me. But I often seek to stretch the boundary just a bit, to show more of my authentic self. For example, not just a string of pearls, but an oversized hunk of pearls, or overly full skirt.

  33. Deja, your blog roll show all has not been working for two days. I depend on it and love it and your posts. Happy spring!

  34. I’ve never been worried about “flattering” my figure because all the things people say are “flattering” are things I don’t want. I’m 5’0″ and I love my height. I have no desire to look taller. But in order for something to be considered “flattering” it has to make me look taller. Also, its usually considered “flattering” to slim one’s hips and bum. I quite like my round bum and wish i had rounder hips. So, I prefer to emphasize those things even though it is often considered unflattering. Fortunately, round bums are becoming more and more appreciated so I likely won’t have to say that for much longer.

  35. You’ve hit the nail on the head here. When I get “dressed up” (i.e. more than jeans and a t-shirt), I tend toward “artsy/creative” more than “figure-enhancing” clothes. While they don’t necessarily make me look thinner or taller, they do make me feel fabulous…and I think that’s the main goal, isn’t it? I’m less interested in cultural ideals of beauty than in expressing my own concepts of personal strength, individuality, and integrity.

  36. Don’t get me started. I detest magazine articles about what you should wear for your body, age, face, etc. We all agree that some things are not flattering, but they are not flattering on anybody. And in my head I now have an image of a pink velvet hotsuit, with a fake tan and sequins, or something equally hideous. But for the rest…We worry too much about trends, how not to stand out, rules, or what a celebrity is wearing and how we can copy it. And we don’t worry about it at all if somebody dresses according to personality. That is troubling. I love people like Jenna Lyons who bend J. crew to fit her personality. But when I see a brand like Isabel Marant, a brand that is so custom made made for the carefree, cool, laid back girl, worn by a Botoxed, controlled, fame hungry celeb I cringe. So flattering should be only about: does it suit who you are as a person. You are absolutely right about

  37. Mmm. love the hair, the glasses, the navy sweater. Like the green trousers (?) on her, but not on me. The shoes? sandals where your toes hang over the front creep me out. I don’t know why, but they do.

  38. What a great post Susan. “Confidence and joy are flattering too in a way that transcends pure physical appearance.” This is what is most important to me. And to achieve it, I find I do need to stick to what is conventionally flattering, even if this sometimes means not conforming to conventional social norms. For example, the MOTB outfit I put together with the help of my blogger friends is flattering and I know I will feel wonderful wearing it, but people keep asking me if my picked out my dress. A dress wouldn’t work well, so I’m not wearing one, even if this means ruffling a few feathers.

  39. Well said. It will help to drive me in the future to consider how I feel and not just how I look in an outfit. Thanks for that!