Monday Musings- Should Flattering Get The Final Say?

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.