Hey, M.A.G., I saw a pic of John Mayer rocking cowboy clothes and a Native American necklace at the same time. Is that...kosher?

I once wore a bolo tie to a wedding—I own more than 100—and a guy who works in the fashion industry asked me how I thought a real cowboy would feel about me wearing a bolo. I thought about it for a couple of days and came to this conclusion: I don't care what the cowboy thinks. I feel no shame about carrying a Filson bag and not being a hunter. I sleep just fine at night in Supreme boxers even though I can't do a kick-flip to save my life.

But I also recognize that this makes me a poseur. And I deserve whatever mockery comes my way. Like when I wear a Grateful Dead T-shirt to the office and GQ creative director and senior Deadhead Will Welch asks if I got it on Shakedown Street. It's my right to rock the tee without understanding, specifically, how he's even mocking me. And it's his right to call me out for it. This represents a balance in the animal kingdom of fashion. Shower me with jokes, but I'll continue to get these amazing fits off.

The problem is stepping into a culture that its members didn't choose to join. Skating, hunting, and cowboying? Those are choices. But when Big Fast Fashion R Us makes jackets with faux kente cloth, or kimonos, or a Native American feather crown, you need to do an audit: a moment between you and your closet when you interrogate the origin and DNA of your go-to garments.

Here's a brief list of questions I like to ask:

Who made this?

Where was it made?

Was this made with good labor practices? (This is always a question you should ask when something looks cool but costs very little.)

(This is always a question you should ask when something looks cool but costs very little.) Did this designer simply knock off that designer?

Were any animals cruelly killed for this?

Can I wear a Pink Floyd T-shirt if I know nothing of Mr. Floyd's catalog?

I'm not here to guilt you. (Unless you're still wearing joggers in 2018. In which case you should feel much shame.) But I am here to help make the simple act of putting on clothes a meaningful exercise.

There's a right way to pay homage to something. Visvim uses some of the same by-hand processes that moccasin makers used way back when. The brand may update something like a pair of moccasins by giving them a futuristic sole, but it does the research. Ralph Lauren makes some of the coolest military pieces on earth. His designers elevate uniforms to honor that heritage. The difference between celebrating and exploiting is a thin line—and usually you have to spend a little bit more money to be on the right side of history.

I'll wear moccasins—although I won't go to Big Fast Fashion to buy them—because I've done the audit. So look at (and into) those jeans or shoes or kimonos. There's enough evil in this world without us piling on in the name of looking good.

John Mayer

Here's something the Internet has known for years: Mayer has reached high-fashion-sensei status.

David Beckham

Carhartt clothing is made for the workingman—and technically David Beckham has a job.

Macklemore

Considering his history of cultural appropriation, I think we got off easy with the bolo tie here.

2 Chainz

Nothing says “grungy skateboarder” like wearing $500K worth of jewelry around your neck.

This story originally appeared in the June 2018 Comedy issue with the title "How to Pull Off (Almost) Anything."

Watch Now:

James Harden Wears the Swaggiest Outfits Known to Man