What I Used to Wear in High School: Dallas Penn

Image via Complex Original

Guess by Georges Marciano was the most prevalent jeanswear in the dipped set. Lee had just ended its run, and Guess was the hot kid on the block from 1985 until about 1992. Guess was really well made early on and their best jeans had leather accents placed on panels. If you had a Guess denim and leather jacket you were a spoiled kid or a dopeboy. I had a Guess denim and leather jacket.

The Coca-Cola rugby caught a wave right after Benetton faded in 1985. The Coca-Cola clothing was dumb baggy, though, and this was how you complemented your tight tapered jeans. In this pic I'm wearing some Prince tennis shoes I copped from a spot on Nassau Street called Spiegels.  That was a tennis pro shop and I was all about finding sneakers that no one else at Brooklyn Technical High School would rock or knew about.  Well, someone knew about the store to send me there. I want to say it was my first girlfriend named Shawnequa.

This was me and Shawnequa in 1986. I'm rocking the Gerry-G colorblocked ski jacket I copped from Herman's with some Polo RL chinos and New Balance 574s. You have to put New Balance 574s in the same space you place Air Force 1s, adidas Superstars, and even your Reebok Ex-O-Fits. Those shoes are everlasting hip-hop because they were dope and accessible. Also peep the Montreal pro model cap. When you were a shorty and you finally got some paper, you copped a pro model baseball cap. Snapbacks were little leaguer status back then, and I had effin' standards.

Polo, Guess, Reebok, and Timberland were basically my high school staples, especially in my junior and senior years. The Polo rugby was harder than anything anyone has ever made. The color palette just popped off the shirt and those crests just signified luxury to a working class kid like myself. I really haven't deviated from the brand too much since the mid-'80s. Yeah, I've bought all kinds of crap that fell under the auspices of hip-hop clothing but none of that shit was as timeless as Polo RL was/is.

Timberland has released several iterations of their legendary Iditarod Super Boot (40 Below), and I still have my pair which was in the box in the background from this picture. Fly hoarder shit.

Oh shit, how could I forgot how hard Avirex was when it first came out? This Avirex varsity jacket put in hella work for me. Steven Spielberg produced a TV show titled Amazing Stories and in this episode all the actors were wearing shearling flight jackets. I murdered the game by buying patches from an army navy store and having them sewn onto my coat. My custom game been crazy since the 1980s. Word to Sean Price.

I got mixed up in a youth collective back in the 1980s called the Decepticons so I didn't graduate from Brooklyn Tech and ended up at the City As School on Carmine Street in the Village.  This school was kids who were too smart to sit inside of a classroom and still too dumb not to know they didn't know shit.  You worked a job as an intern during the week and Friday morning you went to a two-hour session to talk about your experience and had the rest of the day to yourself. I was into stealing cars by this time, and I actually would drive a stolen to the school sometimes. Real talk. I was a dumbass.

This outfit is featuring a Tommy Hilfiger pinpoint oxford, Girbaud twill shorts, and Reebok basketball shoes with Reebok slouch socks. I do have on a snapback, though. Sports Specialties was a brand that made the dopest hats because the crown would be pro model weight wool and the graphic would have colleges and universities who knew where the fuck they were located. Wyoming Cowboys!?

Thirty years later, ain't a damn thing changed when it comes to swagging the eff out.  Your kicks don't have to be Jordans (it helps), but they better be clean.  Your labels should still be something Italian if they ain't saying Polo Ralph Lauren. But most of all who gives a fuck what you have on if you don't?