When I moved to New York City in 1984, the AIDS crisis was in it’s early stages. Heroin was haunting the streets, ten years away from having the word chic attached to it. Wigstock was months away from becoming a glorious sequin sensation and Madonna was filming Desperately Seeking Susan on St. Mark’s Place.

The city was busting with personalities. Scrappy. Shiny. Stylish. Slightly deranged. It felt like everyone was dancing with, for, or away from their own personal demons. The devil we knew was in the details of our day to day. Crisis and political edge often lead to great artistic moments, which to my mind means we’re about due for something great.

But about those Eighties. And Madonna. A woman who moved the needle on gay rights, feet and bodies onto the dance floor and thrift store style into closets across the globe. For me, someone who was fascinated by fashion but poor as a street rat, I’d turned to the second-hand store as my salvation. And in that moment Madonna was my sartorial inspiration.

So in honor of loud, proud and still raising a mighty roar, I’m breaking down a classic Madonna look brought to you by the fine folks at Housing Works, an agency that encompasses so much good work I can’t begin to describe it here (please click on the link to see their full array of excellence). One of my regular stops on thrifting adventures was—and is—their Chelsea store, where not only did I once find a pair of fierce silver sequin pants that made me feel like Deborah Harry crossed with Cher, but I was more than okay with laying down my hard-earned cash knowing it was going to such an amazing organization. Today if you’re in NYC, you can swing by one of their stores, but if you’re not in the neighborhood, you can shop there online (because of course you can). In honor of our summer in the city (leather jacket notwithstanding), here’s how to strut your stuff eighties style in this millennium just like Madame X did back then.

Starting from the top: Bad hair day? Or just simply a hair day at all. The trusty schmatta, bandanna or scarf.

This one is quite peppy. Who doesn’t love a nice stripe?

And you’ve got to shade your eyes from all that cool. What’s more classic than a pair of stylish sunglasses? (I’m looking at you Audrey and Anna.) But just to mix it up a bit, I thought I’d throw in a pair in dark brown with a slightly aviator styling, which is all the rage these days.

And what can one say about the layering of jewelry? It’s a great way to bring the eye away from a defect as I had to do recently after an unfortunate stumble with coffee on the subway: this necklace is an excellent starting point. Go forth and load ’em on.

And don’t forget the bangle possibilities.

A whole series of these would look chic, plus they appear classic but are thoroughly modern given they’re created on a 3D printer. For old-school fun, if you take a close look at Madonna’s wrist you’ll see a whole stack of O-rings, which can be found by the bundle at hardware stores. (If you look closely at my profile picture, you’ll see me sporting a few.)

This T-shirt (although I’m not sure about the tie, but you could get creative with it and wrap it round the back) works with the hair tie on top.

Or you could rock a nice Stonewall T to benefit that awesomeness!

Outerwear? Well I’m throwing in some denim to replace the leather, cuz that’s how I roll.

And I’m switching up the leggings for these:

Because I don’t have any issue with double denim as the canvas!

I know we can’t see the footwear here on Madge, but I took it upon myself to decide these were her thing–and now, because I bought them from Housing Works, they’re mine therefore no link available.

So there it is, my people. Go forth this weekend and celebrate! Life, freedom, style! And the staying power of righteousness.

What do you wear when you take to the streets to raise your voice? (And by streets, I mean any arena where you feel bold and strong.)