John Mayer, the guitar virtuoso and Internet savant, also happens to have a bonkers clothing collection that ranges from hypetastic streetwear to hand-dyed Japanese kimonos. So we invited him to transport his archives to an L.A. photo studio, dress himself, and share his sage thoughts about personal style.

Camp shirt, (S/S '19), Sublig Crew Tee, trousers (S/S '19), suspenders, Seven-Hole '73-Folk boots (2009), by Visvim / Vintage Oyster Perpetual Cosmograph Daytona “Paul Newman” watch ref. 6263, by Rolex

1.

I like the 1940s-man look. High-waisted, not at all worked out, a little meek—in the best way—no alpha-male vibes. Sometimes I wish I didn't have a tattoo sleeve. It just doesn't work with a patterned short-sleeve button-up. Kind of kills the fantasy of it being an old picture. Those boots you see? They shine like that because they've been polished with the splashes of a thousand beers. I wore these every day back when I lived (and drank) in New York City, and they're a perfect example of something getting so broken in they emerge a new kind of perfect. These are from 2009, the first version of the Visvim Seven-Hole '73-Folk boot.

Pullover track jacket (6th collection), by Fear of God / Lhamo robe, and Sublig crew tee, by Visvim / P23A-DS cargo drawcord trouser (F/W '17/'18), by Acronym / Royal Oak Perpetual Calendar watch (early 1980s), by Audemars Piguet / Necklace, by Kapital Pullover track jacket (6th collection), by Fear of God / Sublig crew tee, by Visvim / P23A-DS cargo drawcord trouser (F/W '17/'18), by Acronym / React Element 87 sneakers, by Nike / Royal Oak Perpetual Calendar watch (early 1980s), by Audemars Piguet

2.

What Jerry Lorenzo has done with Fear of God's sixth season is one of my favorite things to happen to artists: a total quantum leap. I just love that at any time, in the middle of a career journey, you can take such a giant step forward that you get a new day one. The older I get, the more I come to realize that's all I'm in search of—the intensity of inspiration that usually comes and goes with your first project. I want it over and over and over again.

SS 101 jumbo jacket (2018), Sublig crew tee, Brigadier Hi-Folk boots (2014), and Border blanket (2018), by Visvim / ALLS/C-AIO jumpsuit (2016), by Neighborhood

3.

You shouldn't let fashion hurt your feelings. If it does, that's a good indicator you're taking it way too seriously. Anybody, at any time, should be allowed to wear whatever they like. Whether it works or not will be for their future self to make peace with. God knows I have a very well-documented history of attempts. Take a hat, for example. Do you know how many hats you have to wear before you find the one that actually works? Wearing bad hats is the only path to a good hat. I'm still trying to fail. I'd like to lose on an outfit one out of every ten times. Means I'm trying. Or I'm not. Did you see how my point just crumbled before me? That's what happens when you try to apply too much thought to fashion.