The “20 Questions” Game Women Play When Getting Dressed

This week, you’ll see a lot of posts about Women’s Equality Day -- the anniversary of women’s suffrage: August 26, 1920. There will be posts about how far we’ve come (a female frontrunner candidate for president!) and posts about how very far we have to go (implicit bias -- as well as explicit, “Trump That Bitch” style bias -- against said candidate).  

From a public policy standpoint, this is indeed a day to celebrate. As we think about how bias and social norms affect women’s experiences, it’s also a day to acknowledge the subtle ways women face a unique set of challenges. Yes, we can vote and there are more of us in the workforce, but there’s still some serious BS we have to navigate, much of which goes unacknowledged.

With the wage gap, discrimination at work, and countless other substantive issues we grapple with, getting dressed may feel like the least of your worries. But, judging from the responses to my Catcalls and Cleavage piece, many of y'all have struggled with navigating your appearances and sexuality at work.

Every time I pack for a trip or just try to put clothes on for a meeting, presentation, or work function, it’s like I’m playing a shitty ladies-only game of 20 questions:


1. Are my clothes “too sexy”? vs. Do I feel remotely attractive?
2. What will make me more uncomfortable, wearing a thong or wondering if I have a panty line all day?
3. Are these pants the right length for these shoes? Will my pants drag when I wear my backup flats?
4. Is my outfit black tie or a black tie optional? When it comes to dresses, what the hell is the difference?

Shoes and Accessories

5. How much pain can I tolerate when it comes to footwear?
6. What shoes are high enough to help me reach eye level but aren’t so tall that they’ll have me walking like a baby giraffe? Or for tall friends: will wearing heels intimidate height impaired men in the audience?
7. Is my purse big enough to carry my backup flats?
8. Is my jewelry too distracting? Too conservative


9. Where will the microphone hook to my outfit for my presentation?
10. Will the first row of the audience be able to see up my dress on stage?
11. Will my outfit show the inevitable pit stains if I start to sweat?  Why are non-sleeveless dresses so restrictive around my armpits?
12. Where can I place my name tag so it doesn’t get stuck in my hair or draw attention to my boobs?
13. How will I be seated for my interview? Is this dress going to show too much leg?
14. Where will I stash my enormous travel purse that’s big enough to fit a toddler?
15. If I find a place to stash my purse, where will I keep my phone, tampon, and/or chapstick since invariably there aren’t pockets in my dress ...and if there are pockets, they’ll only fit tic-tacs.

All The Feels

16. Is my makeup the right level of professional? Why do my fairer skinned friends get asked, “Are you ok?” when they’re not wearing make up?
17. How will other women interpret my looks?
18. How will men interpret my looks?
19. Will I alienate my clients? My peers? My superior?
20. How will my appearance impact my credibility?

For big speeches, I usually end up wearing one of 4 fitted sleeveless dresses with a blazer, the well-loved wedge heels that are most often advertised for their comfort to women decades my senior, and the makeup my friend Mummi taught me to apply for my wedding. After some trial and error, I’ve found a standard combo that leaves me feeling like myself, rather than someone in a Professional Grown-up Lady Disguise.

Why This Matters

It may seem trivial to write a post dedicated to getting dressed, but there’s a deeper meaning here. While we’re trying on outfit #8 and going through emotional gymnastics to decide on an ensemble, we’re missing out on that time to actually prepare for the meeting, presentation, or interview.

Don’t get me wrong, there are plenty of men who take considerable time getting ready (my father being one of them) and worry about pit stains (anyone who lives in the south). But in most professional settings, men can get away with throwing on a suit or slacks and a button down and call it a day. Other than this delicious bit of satire (Hillary Clinton’s husband wore a fetching pantsuit to honor her nomination for US president), there’s very little attention paid to men’s attire in the workforce.

The questions that men are asking themselves don’t have them walking the imaginary and ever-changing line of confident vs. “too sexy”, envisioning the troubling way their appearances might prompt them to get hit on instead of getting the deal.

While we’re walking the tightrope of expectations around professional appearance for women, engaging in the destabilizing internal dialogue about how our sexuality impacts our ability to be successful, men have that time to spend pumping themselves up to be successful.  

Tara Mohr wrote a brilliant piece about attire, describing how frustrated she feels with herself when she invariably ends up in an uncomfortable suit and Spanx when giving a big talk. She writes,

"… How free can we feel – or be – if we restrict our very bodies, by our own choosing?

Because I’m doubtful that women who can’t take a deep breath, and whose underwire is digging into their ribs, are able to give their full energy to what they feel called toward. What would we do or say differently if we could move more freely?

It also matters because in a thousand ways, women conform to and compete within a system that we did not make and that was not made for us. Professional dress is one tangible reflection of this."

As I’ve said before, appearance is one of the ways that women are navigating a more complex environment than men when making decisions about their careers. While we’re celebrating Women’s Equality Day this week, we should also acknowledge the ways our lives are still inherently unequal. Let’s try to avoid Professional Grown-up Lady Disguises and think about ways to feel professional, but also authentic and comfortable in our own skin.

What are the questions you ask yourself as you get ready, and how do you manage them?