What Should I Wear? The Most Dangerous Question in Women’s Facebook Groups

by | Sep 4, 2025 | Style

Image: SFD Media LLC

Honest answers not welcome.

A community where taste becomes “toxic,” and flattery is the only safe answer. No wonder we’re exhausted.

Last week, in a Facebook group of 20,000 women, a single mirror selfie asking “Which dress should I wear?” spiraled from style advice to accusations of bullying, body shaming, and “toxic energy.” All Barbara wanted was help choosing a dress for her 50th high school reunion. By sunset, Barbara, still dressless, had shut down comments and left the group.

Scenes like this play out daily in online women communities: What starts as a simple dress poll becomes a battle over taste, tone, and what women owe each other.

A 2022 UK survey found that around one in five adults aged 55 and older felt anxious or depressed specifically because of their body image, showing that social media-driven insecurity isn’t just a “young woman” problem—it persists into midlife and beyond.

We’ve all seen it. We’ve all taken part.

Scroll any women’s Facebook group and watch the ritual unfold: a mirror selfie, a smile that pleads, “Please validate me.” The responses arrive instantly:

  • The Sweet Liars: “They all look amazing! You can’t go wrong!”
  • The Polite Diplomats: “The third dress is perfect—swap the shoes and you’re all set.”
  • The Truth-Tellers: “None of them work. That cut is frumpy.”

And then the thread implodes.

The Question Behind the Question

Here’s what we don’t want to admit: Most women posting “Which dress?” aren’t really asking about fit or fabric. They’re asking if they still matter. If they’re still visible. If they belong. Many of us live alone, far from grown kids, or are carved out of social circles that shrank with divorce and deaths. The Facebook group becomes our dressing room, our girlfriend, our mirror. We dress up loneliness as a fashion question and hope someone notices we’re still here.

“Asking which dress to wear is a form of a social bid to check and see if we are still on the radar of our friends (it’s a fundamental ‘Do I matter to you?’ barometer check),” explained Gayle MacBride, Ph.D., LP, Co-Founder & CEO of Veritas Psychology Partners, PLLC. “In midlife and beyond, when women are struggling with their changing bodies and trying to reconcile youth culture with their own maturity, this question becomes something bigger as we feel our roles shift beneath our feet.”

The tragedy? We punish the women who try to answer honestly.

The Vocabulary of Weaponized Sensitivity

Honest feedback gets criminalized and terms become character assassinations:

  • Body shaming: Deployed even when the critique was about fabric, not flesh.
  • Toxic: A debate-ender that polarizes everything into “good” vs. “bad” energy.
  • Mean girl: Instant status, even for mild feedback.
  • Negative energy: The polite way to say “shut up.”

Sociolinguist Janet Holmes has shown that women use compliments to build solidarity and preserve social harmony in ways that are often distinct from men, who may use teasing or insults to foster connection instead. This conditioning to avoid conflict is why honesty among women can feel so fraught—it risks betraying the collective sense of belonging. The result is “comment warfare” where speaking plainly becomes grounds for excommunication.

“In general, women and girls are socialized to create harmony and ‘be nice girls.’ … If we are candid, it can violate the ‘be a good friend’ expectation—it’s hard to shake these norms,” said Dr. MacBride. And that’s the catch—honesty feels like betrayal, flattery feels like safety, and we’re all stuck in the crossfire.

The Woman Who Stopped Asking Permission

Marie Thom, of Midlife Dramas in Pyjamas, shows up in riotous florals that break every “rule” about dressing over 50. She posts, “Apparently, nobody over 50 should wear florals. Well, buggery bollox!” Her audience cheers her on. Thom refuses to seek permission and urges others to wear what they please. She still gets nasty comments—but the drama around “Which dress?” disappears when you stop seeking validation in the first place.

She’s not asking which dress to wear. She’s announcing which woman she chooses to be.

Some women reject the whole exercise outright—the “wear whatever you want” crowd. If you like it, wear it. End of story. But for most, the post isn’t really about the dress. It’s about the hunger for recognition—and that’s where things get complicated.

Why We Can’t Stop Policing Each Other

Thom’s confidence looks effortless, but it’s hard-won. Women’s survival once depended on social alliances and reputation. That programming didn’t disappear—it simply moved online.

So, group bluntness feels existential, not sartorial. The real stakes? Belonging.

We’ve created an impossible paradox: craving honesty but punishing those who deliver it. Because kindness can mean telling your friend she’s hiding behind the wrong outfit. And true sisterhood? It requires saying the hard thing.

“Not sharing your opinions doesn’t make you a good girl, it teaches others that your opinion, perspective, and life experiences don’t matter—that’s the point at which we start to make ourselves disappear,” Dr. MacBride noted. “Stand up, have an opinion, make that opinion known—just don’t mistake that for conflict.”

Instead, we offer empty compliments and call it love.

The Price of Pretense

The cost? Exhaustion. We ask for connection but demand compliments. We talk about honesty, then punish it. What’s left isn’t sisterhood—it’s performance. The dress disappears. The honest woman disappears. And in the end, nobody wins. For healthier approaches, Dr. MacBride offered, “For commenters—be specific and objective in your response … I think it’s BS to identify a problem without being ready to wade in with a possible solution … give winning feedback, address two things you love and one thing you might change.”

The Real Provocation

We’ve built a culture where women can’t tell each other the truth. We’ve sanctified fake positivity and confused cruelty with honesty. True confidence isn’t about approval. It’s about not needing permission.

Maybe the question isn’t “Which dress should I wear?” but “Why am I asking?”

Because if every honest answer is branded bullying, the problem isn’t the dress.

It’s us.

If support always means pretending, what kind of sisterhood are we?

About the Author

Susan Dabbar has built a career on reinvention, creativity, and strategic vision, launching and leading businesses across four decades in industries as varied as they are rewarding. Now, as the Founder and Editor-in-Chief of PROVOKEDmagazine, she’s channeling that same energy into a media platform that questions and redefines the conversation around autonomy, ambition, and agency for women.

10 Comments

  1. Just don’t ask. Don’t ask anyone-especially on social media “how do I look?” It’s always a loaded (and disingenuous) question.
    As women in a society that uses the “divide and conquer” method to keep us down, we might try to support each other in solidarity and love.

    Reply
    • I wear what I want. I’m too old to care what others think about my appearance.

      I’m always neat and clean what else is required?

      If you don’t like how I look you’re welcome to look elsewhere.

      Reply
    • Susan Dabbar

      Hi, Such a good point—asking “how do I look?” is rarely about the clothes, and it does set us up for judgment instead of support. I love your call for more solidarity and less divide-and-conquer—we could all use more of that. Thanks for your take… —susan

      Reply
  2. Since chronic pain took over my life I dress for comfort and function. If I can look good doing so, I will. If not, my rule is function over fashion.

    Reply
    • Susan Dabbar

      Hi Maureen, Function over fashion is my go to also, especially when working at home, and hanging. At this stage, I want to be comfortable and covered. (Sun,cold, etc.). That said, when I do have an occasion where I have to look pulled together, I do my best and use my daughter’s opinion to guide me. Which usually means taking a selfie in the mirror and sending to to her in a text. She dishes out the perfect balance of honesty and love.

      Reply
  3. If you are not a fashionista, I understand wanting help to pick something to wear. Google is our friend for suggestions. You will never get enough positive feedback putting yourself out on social media to make it worth the post. Always makes me sad that women can be so brutal to each other and can’t find better ways to feel better about themselves.

    Reply
    • Susan Dabbar

      Hi Angela, appreciate your insight on this one. You nailed it—the internet will never hand out enough compliments to fill the gap, and yet we keep tossing ourselves into the ring anyway. What fascinates me is how quickly “help me choose” turns into “prove your taste is better than mine.” It says more about our own insecurities than the dress. —susan

      Reply
  4. Meant subjective, not subject!

    Reply
  5. Women need to develop the confidence to wear what they like! Of course, depending on the event or occasion, the outfit should be appropriate, and that, too, can be subject, of course.

    Reply
    • Susan Dabbar

      Agreed. Confidence is the point, and “appropriate” shouldn’t become code for shrinking yourself. The line is simple: dress for the event, but never at the expense of your own presence.—susan

      Reply

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