Dressing Like a Woman: The Struggle is Real

At the risk of sounding like your Grandma who stills covers her ankles and wrists, we’ve got a few opinions on how woman dress. And most of them don’t involve body shaming.

We ladies are in a no-win situation. We’re expected to look sexy but also demure. We’re expected to look feminine but also professional. And we’re expected to smile, even when some mediocre man just stole the promotion that we rightly deserved.

But, when we dress demurely, we’re accused of being too plain. When we dress professionally, we’re accused of being uptight. And, when we smile, we’re accused of smiling too much.

When men don’t smile, they’re perceived as being serious. When we don’t smile, we’re accused of having “resting bitch face.”

And, ladies, we know the issues with laughing. We’re raised as girls to cover our mouths when we laugh. Don’t want to have an unattractive horse face. That’s some hogwash right there. If we feel like a laugh, we should spread the joy.

Dressing “like a woman” is a constant conundrum. Do we go for long hair and dresses to please a man? But don’t put that hair in a ponytail lest you look “severe.” Oh, please.

Feminine is as feminine does. That is, you define what it means to dress “like a woman,” whether that means long, flowing hair, a glorious Afro, or a buzzcut.

For Mary Lynn and me, that means whatever hair we want, jeans, flats, t-shirt (or collared shirt for mom), and a blazer. Too masculine? So what? Yeah, we may wear a dress for formal occasions. But my favorite fancy look for myself is tux pants with a strappy top and a sexy trench.

Dressing like a woman is a matter of taste and personality—on top of dressing for the time and place. That sexy top is great for a date but not for the boardroom. Same thing with dancing at the prom vs sitting in the classroom. (I told you we had opinions!)

And what about that tired old trope about women “letting themselves go”?

You know what, gentlemen? Eschewing makeup, going grey, or gaining weight doesn’t mean we don’t care. You try raising kids, holding down a job, and taking care of a man-baby, and let’s see what happens.

We already wrote about basic dressing for women and men in another pamphlet. Go back and read that for our pointers!

It still comes down to wearing what makes you feel comfortable and confident. And yet… flip-flops at a nice dinner or a sexy crop-top at Thanksgiving just don’t work.

One last thing, fellas. Women are never, not ever, “asking for it.” I don’t care if she’s wearing a neckline that plunges so low she needs a Brazilian to maintain a little mystery. That’s still not an invitation for unsolicited comments or touches. (But you know better than to touch without consent, right?)