Old School Cool

Back in the day, Madonna was cute and she had an unconventional personal style. Some of what she wore in her youth reminds me of comments I have seen on Reddit about how dressing gay means, in part, trying to intentionally avoid outfits that cater to so-called male gaze.

I don't entirely know what that means because beauty is in the eye of the beholder and so is sexy. MOST hetero men prefer long hair on a woman -- or pretend to -- but some really dig short hair and some have a thing for bald chicks.

So anything a woman can do in terms of how she chooses to dress or look can be viewed by men as "sexy" and I mostly stopped caring years ago. It's a lost cause in my opinion.

BUT, having said that, Madonna certainly didn't dress as conventionally or traditionally femme in her youth and some of the outfits in some of her early movies and such could potentially be used as inspiration for the LGBTQ crowd in trying to sort out how to be themselves and also be socially acceptable.

Madonna was a big deal back in the day because she was unconventional but somehow managed to be accepted. I have this theory that the hot new thing is anything that is different without getting auto-rejected by most of society for simply being different.

In both Desperately Seeking Susan and Who's That Girl?, Madonna dresses quirkily and it's really not overtly sexy in many cases -- by which I mean she doesn't necessary have cleavage on display and doesn't necessarily have much skin on display. Granted, some people think snug clothes is sexy, but I think of leggings as just comfy personally and it annoys me that you can't wear leggings without some people thinking you are doing so for the express purpose of showing off your body.

Nope.

Anyway, some of what Madonna wears in Who's That Girl? is more conventional, like the scene where she pretends to be Wendy and the white dress with high heels late in the movie. But, really, I think the white dress looks screamingly awkward on her and only serves to highlight how much she does NOT fit into Loudon's social clique.

They no doubt dressed her in the white dress with heels because she finally hooks up with him, so she needed to look traditionally femme in that scene (or so someone thought). But in much of the rest of the movie, she dresses to please herself and is often wearing leggings, flats and covering up her skin-tight top with a loose boy-ish jacket.

The outfits suggest you can be both athletic and pretty, something a lot of women get told is a contradiction.

The tutus she wears in Who's That Girl? are a bit too quirky for my tastes, but I'm also a good bit taller than her. They work on her in part because she's a tiny little thing, so women who aren't so petite may want to try hard to take inspiration from the look rather than trying to outright recreate the look.

Clothes has changed some in the decades since but not so dramatically that you can't take any cues from these looks for dressing today. Bonus points: If you are LGBTQ and need to sometimes hide that fact, you can potentially play it off as "inspired by Madonna" and pretend it says nothing about your sexual identity.