Monday Musings- Should Flattering Get The Final Say?
This weeknd in Vancouver, was trying to prove that summer is over. It’s turned rather clammy and chilly and I see leaves turning on a few trees. I broke out my slicker and red loafers which felt more fall like than my canvas bag. I know it isn’t time to swap out my wardrobe, but it did make me anxious for fall.
This week, I’m musing about the rules we follow without always questioning them.
I’ve spent much of my career as an image consultant helping women understand what flatters them. Color, proportion, fit, balance, and line have been central to my work, and I still believe they’re useful. I rely on them every time I get dressed.
But as I get older, I’m beginning to wonder whether it’s time to loosen their grip.
“Flattering” sounds harmless enough. In practice, it usually means smaller, slimmer, smoother, brighter, or, sadly, younger. Body-shape advice tells us which cuts lengthen, balance, minimize, or disguise. Color analysis works through the very same lens. Which shades make our skin look clearer, our eyes brighter, or our hair richer?
It’s all flattering. It’s all based on the idea that the best choice is the one that improves the way we look.
There’s nothing wrong with knowing the answers. I know which colors brighten my face, which shapes make me appear taller, and which proportions create balance. For years, that knowledge felt freeing because it gave me a reliable way to make choices.
But what happens when when flattering becomes the only standard we use? Getting dressed starts to feel less like preparing for our day and more like passing an inspection nobody actually assigned us. We stop asking whether we like something or whether it feels like us. Instead, we ask what it hides, corrects, or improves.
After decades of knowing how to make ourselves look more flattering, some of us may be wondering whether we still want that to be the goal every time we get dressed.
Lately, I’ve been testing how much of that advice I still want to follow. I still notice when a color isn’t my best or a shape makes me look wider. I just don’t automatically take that as a reason not to wear it.
Sometimes I like the color. Sometimes I like the volume. Sometimes I simply like the outfit more than I care about whether it’s doing everything possible to flatter me.
That may be the shift. I can understand exactly why something isn’t my most flattering option and still choose it.
I’m not abandoning everything I know. Fit, fabric, color, and proportion still matter. I want my clothes to sit well, feel good, and look like me. I just want to keep the knowledge without feeling chained to it.
Have you started loosening your own rules, or does flattering still get the final say?
Reader Questions
Q – I’ve noticed the edge of my lipstick doesn’t look sharp anymore and wondered which lip liner you’d recommend. Am I better off using nude, clear, or tinted? Is it true you should match the color to your tongue?
A – If the edges of your lips aren’t sharp anymore, a lip pencil is a great way to give them a more definition which keeps lipstick from feathering. I’ve never had luck with clear liners that go outside your lip line, but you may. This clear liner is very popular, and this Maybelline liner has great reviews.
A nude liner (the color of your gums) is a great choice because they wear off subtly and don’t leave you looking like you have a ring around your lips. I use those most often. My favorite liner is this one by Charlotte Tilbury. It’s waterproff, budge proof, and doesn’t dry out my lips. It comes in tons of colors…I suggest you start with the “nudes”.
Q – What comfortable, nude colored underwear do you recomend for women over 70?
A – Funny you should ask, because I’m turning 70 in a few weeks and have narrowed down to favorites to only comfy. I’ve long past the age when panties that hit below my waist are either flattering or comfortable. I’ve worn and loved these Natori Bliss stretch cotton full briefs for years and love them!
I discovered these high waisted Eby panties a while back, and love them! They feel like nothing on and leave no panty lines. This summer I’ve gone all in for these cooling, anti-chafe underwear. They are beyond fabulous under skirts or dresses, but I also reach for them to wear under my pants…they are that comfy.
Q – What is your opinion about the leggings we still have in our closet from a few years ago. I know newer yoga style pants are in style, but what about the older ones that we wear with tunics? Should I get rid of mine?
A – Yes. The leggings of yesteryear are very dated now and have been replaced with slim leg, ponte knit fabric options that look more like pants than exercise wear. These also allow you to wear them with slightly shorter tops which look more modern. They’re not as tight so they don’t reveal more than anyone should be seeing.
My musings are me working things out and I’d love to hear your thoughts on “flattering”.
When leggings started to go out of style, I did not want to up my silky-feeling J Jill leggings. Instead I repurposed them as thermals to wear under pants when walking my dogs in the cold weather. They’re lightweight and not as constricting as some of the thermals I own.
Great idea Linda
Happy Monday, Jennifer. I love your Monday musings. They usually make me stopp and think. In regards to today’s topic, I think it’s important to choose your clothes with consideration of how flattering they are, but not to make it the most important reason for selecting the components of your outfit. Practicality, appropriateness for what you are going to be doing, and how they make you feel physically and mentally are more important. As an example, I have a red crew-neck sweater that my late father wore for years. It’s a cool red that doesn’t really suit my completion, the sleeves are too long, and it’s flat out too big (Dad was 6’1″ tall and I’m 5’4″), but when I wear it, I feel like he’s giving me a hug. I reach for it on cool days when my mood is low and I want to feel better. Wearing it reminds me that no matter how sad, tired or lonely I am, he’s still with me. Other pieces I wear because I love the fabrics they are made of–how it feels against my skin, how it drapes (or doesn’t), etc. While I want to look nice, I don’t have a need to look “perfect” in my clothes before I head out the door anymore. Besides the most flattering thing a woman (of any age) can wear is a smile.
That is so beautiful and you’re so lucky to still have his sweater. I was in my 40s when we lost him and frankly, out of my mind with grief so I didn’t have the forethought to keep one. When I picture him, he was always wearing a cardigan I knit for him and that would have been what I’d wear for the hug. Thanks for bringing him back to me today xo
Thank you for these daily posts. It is evident that you put a lot of effort and time into them, and they are so helpful. You have led me to make more thoughtful decisions about my wardrobe. I appreciate you.
First comes comfort, whether out all day, or staying at home. Soft cotton or bamboo that doesn’t bind. I’ve found that smaller companies who specialize in comfort also specialize in flattering styles with lots of color options. It’s a different life for those of us with auto immune diseases.
Wear what’s comfy and brings you joy!
Boy, Jen You always give me room for thought regarding my wardrobe and choices. I hope when I make new purchases I am looking at flattering. It is certainly a strong consideration along with other things. My color palette is just something I have learned to migrate towards as knowing the colors I look my best in is going to be a strong contender.
I really do not look outside of my palette because why would I knowing what I know?
Thx so much for the great questions and mental fashion stimulation, always.❤️
I don’t think of it so much as rules – I am just naturally drawn to clothing and accessories that I know will flatter me. I guess that comes from the wisdom and instincts built over the years (turning 70 soon too!) With costs being what they are, I choose to go with what I know will work best for me, vs costly experiments.
I recently saw some photos of myself and absolutely hated the shirt I had chosen and how it made me look. I realized the neckline was completely wrong for me, so I went back and re-read your article on necklines. Very helpful. I realize a v-neckline is my most flattering. So, does that mean I throw all my round neck tops out and start over? No, everything does not need to be flattering, as you’ve pointed out here.
You could also add a long necklace to draw the eye up and down or drape a narrow scarf tied like a man’s tie with low knot.
At 4’10” and around 90 lbs. , yes flattering is good ! I like to look taller. Shoes help, stripes, rolling sleeves up or pushing up, cuts, etc. I am alittle bit older than you and I wear Soma tummy control and invisible edge panties. If you care about panty lines these are great , especially under white jeans in summer. Love the ones you wear too! Can we talk about gapping in waistline in jeans sometimes? NYDJ and Democracy don’t but wonder if other petite or misses ladies out there have the same trouble? Thanks for helping us!!
Bonnie, you’re not alone. Jennifer, I second Bonnie’s request. Thanks!
Thank you for answering the question I sent in a few weeks ago about underwear!
I hope it helped Claire.
At 68 (wow that looks old!) I have realized some outfits aren’t my most flattering but they are current and in style. I guess I am comfortable with this, although I must say I am getting tired of the wide leg pants as they are not my best look. I think that it is wise to know what works best with our body and personality and then be free to “break the rules” for something we love or just feel like wearing. As always you make us think!
I will also turn 70 (in February) so your post hit home for me. I still want clothes to flatter me but I’m not chained to the idea enough to follow every trend or, God forbid, be uncomfortable. Let’s face it…other than our spouses/significant others and maybe our closest friends…nobody is really looking at us. They are all too busy looking at their own selves and their own social circles.
Ha, down with the patriarchy! Because what is “flattering” if not dressing to be desirable to men? I’ve been chewing over that a lot lately. The youngs call it being a “pick me,” and isn’t that what women are conditioned to be? It’s so ingrained and difficult for our generations to move past, but I’m ready.
Exactly Shari! I’m ready too
Thanks for the opportunity to be honest. I have a few outfits that I wear quite often that probably do not meet your definition of “flattering”. Why do I wear them? Because they fit my lifestyle and they do not require me to repeatedly look in mirror to adjust a waistband or re-tuck a shirt. They work for me and I know that I will be comfortable all day. I also wear colors that I shouldn’t wear, according to the experts. Certain colors just lift my spirits or calm my nerves, so why not?
Yes! Enjoy
I’ve been buying the Natori briefs for years now based on your recommendation. I love them and are worth the cost in my opinion. As far as being “flattering” 100% of the time. I think well groomed is enough as a baseline. I’m having a problem with many of the influencers for us women over 50 that think every step out the door is a fashion shoot. I agree that if we’re attending something where photography is a certainty that neutral solids are probably best. One blogger (who I actually like and agree with about 75% of the time) described Lilly Pulitzer prints as “hideous.” Well when I’m visiting my grandchildren they love those prints and make them happy to see me and the “kid stain causing moments” with them don’t show up as easily as my solid tops will. So I happily sacrifice stylish perfection for them every time.
Lily Pulitzer also looks fabulous when in Palm Springs, Florida or tropical climates. Her dislike is her personal taste. My goal is to help readers hone their own personal style so that they curate a wardrobe that confidently reflects themselves. I hate capris but if it’s your thing go for it. I’m not here to dictate what you should love.
Lovely musings… thank you. I am still working in my early 70s and striving to be perceived as in indeterminate late middle age. It is important to my public role. This does involve more time with preparation for the day! And for me that also means clothes that fit and flatter in an up to date “classic” style. I carry over that approach to the weekend because most of my wardrobe can multitask.
I too am turning 70 soon and this resonates with me. I’m still working — hoping to retire soon — and actually have been fantasizing lately about when I can get rid of all of my work clothes and just wear what I like.
That will feel freeing
I have always loved a slim leg look and those Spanx Ponte pants is something that I would wear. It looks to be a higher waist and that is just what I like.
You gave me pause when you said, “Instead, we ask what it hides, corrects, or improves.” That really keeps our focus on what is WRONG with our bodies and is a rather negative way of starting our day! I would rather focus on what makes me feel good, comfortable, happy instead of on how will others see me or on how will I be judged. Maybe a gentler approach is to relax our self-criticism a little and simply avoid wearing what is truly unflattering without the high-bar requirement of “flattering” every time we get dressed.
YES! That’s where my thoughts are going with this Carol.
Jennifer, I love the manner in which you dive into a subject. The thing about a flattering or unflattering style for me is that I will buy something that is a newer look, but it doesn’t really work for me. Cropped shirts are an example. I purchased a darling yellow and white striped one for summer, but every time I see my full length in it, I question why I’m wearing it! Not flattering in the least! I think that we all wear unflattering pieces, but I think that flattering could almost equal comfort. When one looks in the mirror, are you comfortable? I so look forward to reading your blog. You are wise and very funny! Kathleen
If the unflattering shape offends your eye, that’s not comfortable. You need to feel good in it. I’m finding I can feel good in things that aren’t specifically trying to narrow my shoulders or length the look of my legs.
Jennifer, I have to be honest here. I don’t think I can give up looking for flattering outfits. Clothes that flatter make me feel comfortable and confident. When I find something that makes me look taller, slimmer, and younger, I buy it! Then I wear it with joy.
You certainly don’t have to give up flattering. I don’t plan too. Enjoy what makes you feel confident.