I am a 34 year old white American male who has spent at least twenty five years fretting over style choices. I want to be unique but I do not want to draw too much attention. I want to fit in, but I refuse to wear many of the style conventions of the day. I want to appear timeless, but also to reflect a specific time in history. Above all, I want to have clothes that actually fit and do not fall apart. Satisfying these requirements has been a constant struggle of my adult life. In an effort to chronicle my journey through this admittedly shallow and unimportant issue, I will focus on the one constant of my attire - the blue jeans.
The year was 1991. I was a nine year old child in Birmingham Alabama attending a typical private mostly white middle school. Styles were changing drastically from the late 80s. Blue jeans always had their place in the cultural style of the time, but the notion of a fashion designer jean hadn't been invented. You had Levi's and a few other brands which mostly espoused the cowboy western vibe. There were certainly avant garde artists and musicians who wore jeans, but it was seen as a low class working man's attire. Levi's made one style of jean, and it was called "levi's". They were stiff as all hell and took years to break in, but they were essentially indestructible. Today they call them "501 style".
Things began to change (from my perspective) when Levi's started running these "Big Jeans" commercials. They had embraced this laid back surfer/skater style and started making jeans that were deliberately not for cowboys. I was nine years old, and the commercial essentially won me over. I would argue that I viewed it from an intelligent strategic perspective though. To navigate middle school, one must dress appropriately so as not to be singled out and mocked. I desperately wanted to wear the right clothing in order to avoid any attention. I knew not to try and keep up with the raw cutting edge fashion, but rather to ride the wave of being current, but not too current.
The answer was Levi's "big" jeans, graphic t-shirt, and an unbuttoned plaid flannel. It was essentially exactly what you might find Eddie Vedder wearing. I wore this exact combination every day until I was 14. I was mirroring the grunge style that was slowly taking over the legitimate fashion world, but really I was just copying the older kids and the commercials I saw. By the time I was in 8th grade at age 13, I had some more confidence, and started to wear more jet black levis. This was 1994. The fashion world had changed their stance on blue jeans, and now all sorts of clothing companies began making their own jeans. The change was rapid. It was like the SUV craze of the later 90s. Nobody made jeans, then everybody did.
This was the time that hip-hop culture invented saggy jeans. Like the zoot suit of the 20s, the saggy jeans deliberately use more fabric than necessary to proclaim opulence. Jeans now exuded hipness, and came in a rainbow of flavors from many different designers. "Loose fit" was the buzz word they all shared. Your choices might be "classic, loose, or baggy".
I remember corduroy came into fashion and everyone was wearing slacks with fairly muted earth-tones. The overall trend was to wear baggy clothes, which often translated into just buying the "large" size of everything. It was slightly absurd, but I suppose it was a boon for the parents at the time who had children going through their growth spurts. I remember having a pair of black corduroy pants cut in the style of blue jeans which had a 35 inch waist. This was easily 5 inches too big for me, and I had to wear a belt that doubled over the waistband to make them appear to fit properly. One look that I loved was to wear a denim button down shirt tucked in over a white t shirt and black jeans. I am not sure where I picked that up, but it was a look that was everywhere it seems. I remember planning out my week to make sure I wore that outfit on friday. I shudder to think what I looked like then.
In 1997, for grade 9, I changed to a different school, and drastically toned down my wardrobe. I had some super generic levi's jeans, this time just the classic cowboy style. I would wear a baggy graphic t-shirt over this. This began my quest for the perfect graphic t-shirt, but that is another story entirely. The short version is that I witnessed graphic t-shirts go from sincere to ironic to manufactured ironic to what we have today, which I might call "crowd sourced ironic" t-shirts. Suffice to say, my goal was to have a t-shirt that not only fit well, but also endorsed something that was either funny or genuine. It couldn't be too funny, or endorse something genuine which was embarrassing. Self-deprecation was fine, but it requires confidence and popularity, which I did not have starting at a new school.
My outfit also included some generic GAP brand khaki slacks, which were accepted post-grunge attire. My school was actually fairly avant garde and stylish, so we tended to shun certain trends. One trend that we were not able to avoid was Abercrombie and Fitch. This brand went from being completely unknown to being the uber-hip store for teens in front of my eyes. I personally shopped there more than I'd like to admit. The aesthetic was fully embracing the post-grunge look - casual button down shirts, baggy jeans, surfer necklaces, etc. It was great to have a store that sold all the grunge attire I wanted, but was new and from a brand that had been accepted as cool.
Abercrombie worked alright for me to a point. Their clothes were always designed for some kind of gorilla-man. To fit properly, you are expected to be a card-carrying oaf. I have never been truly "slim", or "small", especially in my shoulder breadth. In order to fit my shoulders, the clothes were always too long. I stuck with them because the brand was guaranteed to make me fit in at school.
I need to emphasize how much internet shopping has revolutionized life for the stylish neurotic individual. Not only did I have to choose a style, but I also had to physically go to the store and make eye contact with a stranger while I told them what pants I wanted. This wasn't completely debilitating, but it was overwhelming. All things being equal, I probably would have shopped at Hot Topic, but I didn't have the confidence to do that. The Goth look was becoming more notorious, and I enjoyed being among the counter-cultural types. I never had the nerve to commit to the Goth lifestyle, but I did want to dress in black.
My tipping point began the summer of 1998. I mentioned wanting to get a black shirt from Abercrombie and Fitch, and a friend informed me that they do not sell black clothing. I found that remarkable, but upon further scrutiny I realized it was completely true. I felt the need to shun this growing neo-hippie jam band vibe that always seemed to dress in Abercrombie attire. Dave Mathews Band had released Crash in 1996, and now his music was becoming a way of life for the late 90s redneck group. Elsewhere they may be identified as fratboys, and today we may call them 'bros', but back then they were jam band rednecks. I felt the intense desire to disassociate with this vibe, so I stopped shopping at A&F, and stopped wearing their clothes.
This was also the time that my sister had a drivers license and knew where all the thrift stores were. Buying secondhand clothes was fantastic, mostly for the ironic t-shirt opportunities. I also began wearing clothes with just the right hint of obsurdity. I had some slacks that were just black with a stripe down the leg, but they were clearly made for a marching band uniform. I also had many pairs of cargo shorts still, which remained valid long after summer in Alabama. I still wore blue jeans most of the week. Abercrombie jeans had never fit me properly, so I moved over to the GAP. Their brand of generic straight leg jeans were actually perfect for me.
I did learn that the GAP jeans do not last terribly long. I watched my go-to pair fall apart tragically a couple times a year. In the school year of 1998-99, I started to fall into the new raver style of the day. The JNCO style jeans with enormous legs were actually cutting edge and weird in their day. I had friends with some jeans that barely actually functioned as pants. I kept my choices within the realm of sanity, but still fully embraced the style, which had a lot of crossover with the skater crowd. Pop-punk music was becoming more and more valid. This was the year Blink-182 essentially broke onto the national stage. I find it slightly ridiculous the amount of respect they get nowadays, but whatever - the music was never really my thing. My look in 1998 was raver/skater, but I was mostly listening to classic rock and pearl jam. I enjoyed Nirvana, but it was always Pearl Jam that I defaulted to for music.
It was that year that my sister sewed inserts into a pair of levi's I had to make them into bellbottoms. It was ridiculous and silly, but at this time I was confident enough to welcome the attention. My highschool headmaster literally hated me for them I think. I ought to restate how the trend at the time was leaning towards absurdity, and I did attend a very artistic intelligent private school with no dress code. I had my bellbottoms, but my friends had their oversized jeans, thrift store tuxedos, or a luxurious purple housecoat with frills at the cuffs. That year the dress code was amended to include the prohibition of anything deemed "outlandish". Outlandish is a great word, and it fully empowered the faculty with the power to veto anything. I do not blame them.
That year was great for me. I got my own driver's license and access to a car. At least my anxiety over requesting a ride to a clothing store from my parents was now alleviated. Most weekends my friends and I would go to the thrift stores in search of new clothes and ridiculous artifacts.
That all changed dramatically my senior year of high school. I am still slightly baffled by the shift in trends, but I suppose it makes sense, albeit stupid. Basically I feel that the Grunge movement was more than just music - it reflected an overall frustration with the manufactured nature of culture. Unfortunately the rejection of 'the man' did not last forever. Between 95 and 98, "hippie" culture flourished. There was an overarching opinion that "the 60s" were great and important and worthy of celebration. I do not dispute that notion, but I feel like the story of "the 60s" was widely misinterpreted. When people refer to "the 60s" they often are referring to 67-69 only, which is a minor gripe of mine. The Grunge movement espoused certain ideals of hippie-ness, namely the shunning of mass produced products and living a simple, free life without a concern for traditional notions of appropriate fashion and grooming. This combined with the aging baby-boom generation to create a variety of cultural trends tied to the ideals of "the 60s". Tye-dye shirts, long hair, and there was a goddamn 2nd woodstock.
Lets return to blue jeans. The neo-hippie movement of the mid 90s had its influence on blue jean fashion in a few ways. The baggy style jean of the early 90s had diverged into the enormous raver/hiphop attire, and the more classic designer "slim" fit. Most people were still wearing a roomier jean which still mirrored the old cowboy style. At some point around 1996, one of the many jean designers decided to embrace the 60s vibe with a pair of bellbottom flared jeans. The trend took hold, and by 1997-98, every single pair of womens jeans had a wide flared leg. It was less pronounced on some pairs, but for a period of time, you could not find straight leg women's jeans, let alone tapered. At this point, the men's jeans did something slightly odd, which was to ignore the flared leg trend almost entirely. Women's jeans with the least amount of flare were called "boot cut". There was a "boot cut" jean for men, but what this meant (to abercrombie at least) was to actually cut a vertical line along the seam about two inches at the leg opening.This allowed the jean to open wider around a pair of boots theoretically. This literal cut was everywhere between 97-98 it seemed.
In the 60s, blue jeans didn't really come in a bellbottom style at all. The whole idea of flare legged jeans was an anachronism from the start. Regardless, they became my own white whale. Eventually even men's jeans began taking on a flare at the base, though they were still often referred to as 'boot cut'. I remember returning to the GAP when I needed generic, non raver, jeans, and being satisfied with their boot cut style. I preferred a wider flare because I wanted to look like Robert Plant essentially. Any rock icon of the early 70s really. The GAP jeans weren't flared enough, and they tended to fall apart. I recall they came apart on the front of the thigh from my keys in my pocket, and also at the top corners of the back pockets. I really did check every store, even looking in thrift stores for gems from the 70s. Male bellbottoms were basically a no-go.
This is all leading up to the style shift of my senior year of highschool. I am sure every 18 year old believes their experience is uncommonly transitory and revolutionary, and I am no exception. I have perspective now to understand that everything is in constant flux, yadda yadda yadda. Be that as it may, the fashion world did take a dramatic turn and I watched it happen.
As I said before, the years of 1994-1998 saw the typical highschooler (and 20 something) dressed in a loose fitting t-shirt and jean combination. It reflected the laid-back hippie style mixed with modern grunge and marketed by generic clothing stores such as the GAP and A&F. For some reason, the style shifted from a laid back casual attitude to a much more dressy clean cut look. Many many guys who had worn their hair even just slightly long were now getting close cut styles and using hair gels. The polo shirt and the tucked-in dress shirt made a huge return, and guys were wearing slim khakis instead of jeans. Golf became popular among highschoolers. Guys dressed like the evil rich kids from an 80s comedy. Sweater vests, for gods sake!
I recall a few specific touchstones. The Backstreet Boys, for one, shocked me. Having fully digested every single episode of VH1's "Behind the Music", I had this sense that "boy bands" were a done deal. In other words, society created The New Kids on the Block, and we are all embarrassed for endorsing them. It is completely idiotic to think that another boy band can work with the same formula. We all know how that worked out.
This was also the year that saw Puff Daddy rise to fame. I never paid too much attention to the Hip Hop world but, I was always aware of it. The gansta rap of the mid 90s had apparently waned to the extent that an artist like Puff Daddy was now allowed to be famous. I am certain that there is more to the story than this oversimplification, but it seemed to me that Gangsta Rap was a reflection on the reality of life, whereas this new generation of artists were