Long before Scott and Garance won a CFDA media award and street style became a phenomenon and source of emotional distress, there was Vice Dos and Don’ts. It began as a column in the print magazine (an ASME National Magazine Awards finalist for General Excellence) and evolved into a daily section of their site that I first heard about when I moved to NYC about six years ago and checked often for a frequent dose of hilariously captioned photos of hipsters (and, if I’m being honest, maybe to do my best to make sure I stayed within the “do” category).

Vice just launched the second book installment of Dos & Don’ts, described on the back cover as representing “the most incisive and honest commentary on street fashion in the last million years of humans wearing clothes.” Which it might very well be. One of the people responsible for that commentary is Dos and Don’ts editor Thomas Morton, who over the phone yesterday told us all we ever wanted to know about the feature and then some.

As he more or less speaks in witty, irreverent Dos and Don’ts captions, his answers were entertaining to say the least. From the seamy places those photos come from, to how hangovers factor into caption-writing (heavily), to where he believes style really comes from, read on for our interview with the man who made it all come together.

Fashionista: What was the process like putting the book together?
Thomas Morton: We just started building this ever growing dogpile of do’s and don’ts. The first [book] took about 10 years or so to accumulate 200-250 pages and we had enough for a second book within a year. You can picture this mound of elephant crap just growing and growing and not knowing what to do with it, so we made a couple attempts at squeezing everything in, but it would look like a phone book or some kind of enormous Catholic bible, so we just kind of decided to do a best of.

How did you decide which ones were good enough to include?
I’d like to say there was some sort of system or that we ran market-style surveys or focus groups, but all the ones that we orchestrated in shopping malls in New Jersey kind of left us with a weird crappy selection. So, we just went with our gut–the ones that we liked, the ones that we thought were funniest, that had the best pictures.

Wait, did you actually set up focus groups in New Jersey malls?
We set up at Woodbrige [Center mall in New Jersey]. Right outside the Chick Fil-A we had some tables but we couldn’t do it officially–we kind of got chased off by security, but the thing is they’ve only got two security guards there so those guys would run us off and we’d just wait about 30 minutes and there’s like an Orange Julius that’s not part of the food court; it’s like on the other side, so we’d hang out there for a little bit, wait for them to get all the way down to the JCPenney and then set back up and we’d have another 45 minutes, which is more than enough time. [Ed. note: still not clear on if this actually happened]

Where do the photos come from?
Very often, the best Dos and Dont’s-takers are people who do nightlife photography. Or DJs. One of the best ones we have is this guy Vito Fun, who DJs all these gay circuit parties and goes out to Fire Island every weekend to these older gays’ houses. It’s these people who, by the nature of their job, are forced to go into some of the seamiest, not necessarily dangerous, but kind of grossest little corners of New York nightlife. Especially the places that aren’t fun to hang out in often yield some of the best people kind of taxing the limits of style and of taste.

Do you also get submissions?
[Yes,] actually cell phone cameras have gotten to the point where they don’t look completely blown out in print so that’s been a complete revolution in terms of what we’re able to use and run. That opened the doors..that’s our Gutenberg press moment. And we have editions in like 35 countries right now or something ridiculous, so all of them send us stuff too which is great because people in Romania dress like shit. Actually, they dress like clowns. That’s actually a little more accurate, like they’re actually wearing a clown costume in their day to day affairs especially if they’re over 60.

What is the caption-writing process like?
It is a writing team that I’m a part of and we kind of just build them out and do little clusters of 20-30 at a time depending on how much free time we’ve got and how hungover we are…and what style of hangover. Like [if you were] solid beer drunk, it really supports the process. [If you were on a] coke and whiskey bender, you can get a little bit depressed the next day. You can always tell what somebody’s been out doing by how sad and despairing [the captions are.] The author is always present.

So do you try not to overthink them?
There are some you can tell it was someone’s gut response. There’s other ones where you just mull over this one thing, this one decision somebody made to put this ridiculous beret on top of an otherwise complete pvc Hellraiser get-up and you create in your mind this new subculture that someone’s the pioneer of or at least some kind of ambassador for. It either comes to you in a minute or you have to spend an entire night devising basically a whole Marvel comics multiverse new world whose rule, you have to assume, somebody’s following. You can’t hit the middle ground–that’s when it gets lazy.

Is there a formula to determine who’s a do and who’s a don’t?