The Bullying Effect of “Effortless Dressing”

If I feel uncomfortable — maybe that’s on you.

Hey Mrs. Solomon
6 min readDec 11, 2022

I never felt much for “manners” until I read something that caught my heart. That the purpose of manners isn’t separating the classes. Or honoring some now needless and dated tradition. The purpose of manners is to make people feel comfortable. Here, I think I dug up the actual quote.

“Good manners is the art of making people comfortable. Whoever makes the fewest people uncomfortable has the best manners.” -Jonathan Swift

In manners, you create a system that makes it clear what to do in awkward moments. And these rules remove the awkwardness of them. So we can get back to our purpose — the exchange of ideas, large and small. The celebration of each other’s celebratory moments.

One way I celebrate moments and honor people I love is to dress up. So the idea of going to someone’s home for a festive holiday in jeans — that’s just not me. And also, at some points in my life, I’ve just felt more comfortable in skirts and dresses and heels. Pants and shorts were just hard for me, for a variety of reasons. And there are articles of clothing that, to this day, I just cannot feel my inherent self in. Like a down jacket. If I put this item on my body, I feel too try-hard, ironically. I feel like a poser. I feel the opposite of what dressing should make you feel: settled in yourself. The combination of these things has led me to look out of place in some situations at various points in my life.

The one that stands out the most in my memory, was when I was invited to dinner at a college classmate’s home. I don’t remember what I wore. But when we sat down at the table, her mom said: “My, someone’s all dressed up.”

I actually said: “I just wanted to honor this nice invitation.”

She made me so self conscious. And she really hurt my feelings. I mean I’m still talking about it — it happened around 1991.

In a recent IG post that my friend Rose @thecreativeclassicist referenced, stylist Allison Bornstein called out “looking like ‘we didn’t try’ “ as a “Low-key sort of degrading ourselves to protect and uphold this image.”

Effortless dressing is really, really effort-ful for me. Yes, I now wear pants. And even shorts. And sneakers. And flats. But when I pull this all together, no matter how easily it happens IRL, it doesn’t always end up looking effortless. And it often takes a lot of effort to get a “casual” look to feel both easy and like me.

I’ve come closer lately since discovering @amysmilovic and Tibi Style Class (forgive me for sounding like a broken record on these things; I just feel compelled to be truthful and also to give credit). My eye has changed, and along with it my wardrobe, and I’m drawn to things that look more “eased out.” So the tools of effortlessness are at least in my closet. And often a look comes together easily and looks easy — the holy grail. But other times, trying to get out of the house looking less try-hard, is such a struggle and takes so much trying. That I end up annoyed with all of it.

Interestingly, now when I want to look effortless, at 50+, it’s generally for myself. More and more I’m dressing for how I want to feel at a particular time. And effortless is often how I want to feel. So it’s worth the struggle and all its irony.

But what about those moments when I’m dressed the way I want to be dressed and I get these comments, these “wow, you’re fancy” and “wow are you going somewhere else after this” comments?

Amy has an answer. And her answer is in the incredible pieces she’s developed that instantly telegraph a casualness. The pieces I now have in my closet. Tools, I think she’d call them. Like athletic pants that happen to be perfectly designed to be so much better than athletic pants. The perfect sweats that somehow don’t make you feel like a poser because they’re designed just enough. Sporty, anorak coats that seamlessly blend form and function. With nary a North Face in sight.

I deploy many of these things, and they are game changers to be sure. When I want to wear the lace crop top I love during a normal afternoon lunch with a friend, putting it with Tibi nylon pants calms it right down. I’ve also learned from watching her brand and the Style Classes, some styling tools that also help. Things like wearing a men’s belt casually looped around itself. Mixing gold and silver or pairing a brown belt with the black outfit to take the matchy preciousness away. Or tying sweaters haphazardly (ha! Not really!) around your waist. Tricks to look effortless. I deploy them all.

Nylon athletic pants from Tibi chill out my lace top

I am grateful for all of these answers. And I don’t need to be this person who sticks out like a sore thumb and then just says “this is me, deal with it.” There’s something insistent and self-absorbed about that, unless you are (as Amy has referenced) Dolly Parton. Or Diane Keaton.

But I would just like to turn the conversation to the people who make these remarks. Like my old friend’s mom.

If good manners is making others feel comfortable, why does all the onus have to be on me or on anyone to dress effortlessly and fit in perfectly? Sometimes for whatever reason I just can’t. Or maybe sometimes for whatever reason I’m not capable of trying that day. In some cases, I imagine there are much deeper reasons why people can’t dress to fit in (body acceptance issues, financial limitations, infirmity, cultural mores). Why is the conversation always about how we can be more “effortless” and not about the bad manners of those who make us feel we need to?

I remember reading in some manners book that when someone at a dinner party makes a faux pas, the ideal manners dictate that you make the same faux pas just to make them feel more comfortable. For example, if someone drinks with the wrong glass, you don’t correct them. You proceed to drink with your wrong glass and everyone else adjusts too. That’s manners. And it’s kindness.

These up and down looks and the comments that seem to be throwaway remarks — “Oh, where are you going?” or whatever — are passive aggressive little digs. They’re mean.

I go back to this time when my son was in preschool and we were taking the train home. And seeing an older man with a large beard, he shouted out “look, Mommy that man has hair where his mouth is supposed to be!” He was four. And of course I told him that was not ok. Shouting out (literally or with looks, jokes, whispers) other peoples’ differences is not ok. Not at 4. Not ever. Part of growing up is reaffirming and recommitting to that over and over.

But instead of focusing on this effort, we seem to focus only on asking women — and notably, it only seems to be women — to be “effortless” all the time. To blend, in any situation, like perfect little chameleons. We’re supposed to perfect our no-makeup makeup. Not only to get a kid to the hockey game but to get there looking like we fit in versus just came from an intense meeting or whatever. Sure I’m grateful to afford effortless style tools for when I want to feel that way, but that’s a rarefied world.

And by the way, when I go to an event and I don’t feel like someone’s dressed up enough to honor the situation we’re in, I sure as hell don’t make them feel that way. I don’t say “nice of you to get out of bed.” Because that would be douchey.

I just wish there were less writing about “effortless style” and more writing about the real meaning of manners. I wish more people were writing about what to do (or not do) when confronted with differences, from the mundane (fashion choices) to the more significant. How to locate tenderness, suspend judgement, and focus on connection. Or if all that’s impossible, at the very least to keep your mouth shut.



Hey Mrs. Solomon

Grown-ass woman. Perpetual student of style. Sharer of tips. I work @honorcodecreative and write about fashion and style ahas here and on IG @heymrssolomon XO.