Late 1990s: still not really getting it, but the company is still wonderful

Let’s Play Dress-Up: The Rambling Preamble

It has been my intention, forever derailed and distracted from, that Teleport City would spent time here and there discussing style and clothing. However, I did not want to simply reiterate and regurgitate, and I did not simply want to post an occasional photo or comment about some fashion show that recently happened,especially since I more frequently attend shows revolving around the removal of clothes rather than the donning of them. So what was it, in other words, that Teleport City’s peculiarly skewed perspective on the world could bring to the table that might prove different than the usual, even the usual I enjoy reading? I decided I would keep mum on the topic until I could come up with an appropriate angle from which to approach it. And I think I finally have one.

In my long and still a long way to go journey through dressing myself, I have made many bad calls, ended up in many cul-de-sacs, and generally been lost and confused. Style guides are common, but so many of them seem to pick up the subject with the assumption that we are all tottering down the street with the means to pop into the local bespoke tailor and drop a few grand on a new suit or pair of shoes. I wasn’t that person. I’m still not. And few articles about style seem to acknowledge the fact that, for many of us who want to dress well, $1,400 is not a bargain, no matter how exquisite the craftsmanship. Heck, for most of us, $400 is an impossibility, and $40 takes some careful planning.

So I thought I would take a stab at weaving my own sort of guide, one that would have been more useful to the younger me, and one I hope will be a handy guide for many of you who, like me, are often priced out of the well-meaning other entries in the field for whom money, location, and practicality seem no concern. This is not an attempt to tell you “the rules” of dressing — you can find those elsewhere, and let us address this right now: for a basic day-to-day guide and foundation work on current sartorial affairs, you should pick up Esquire Magazine’s The Handbook of Style. It covers the basics and a little beyond with much more authority than I could ever hope to muster. For more advanced forays, with an extra dash of history, pick up Dressing the Man.

We will certainly be interacting with and mentioning “the rules” when appropriate, it’s not my goal here to simply reprint them with a line or two of commentary. This is also not an attempt to convince you to go dandy, or at least a little dressier. From the point where we stand now, the assumption is this is already something in which you have interest. I’m not going to campaign against your Crocs and Dockers get-up, no matter how tragic I may think it to be. So if you are happy where you are and adhere to the modern obsession with casual dress, god speed you and good luck. This article is not for you, and we are not here to try and debate you.

While the topic here will lean heavily toward what is traditionally thought of as “menswear,” as that is the area with which I am familiar, we in no way mean to imply that this is a style guide for men who want to dress like men. Gender stereotypes and expectations are boring, at best, and — more tragically — unoriginal. I will say menswear because that is the word we have for the particular types of clothing we will be discussing. But don’t let the limitations of vocabulary limit you. This guide is as much for the women of Teleport City as the men, and a woman in a well-fitting waistcoat and tie is as welcome in our parlor as a transgendered person who knows how to wear an elegant cocktail dress. And everything in between. This is a well-clad society of dandies and devils, cross-dressers and quaintrelles, butches and bosses, femmes and fancies. However, if you are a woman with a taste for menswear tailored to your body, I highly recommend you also check out Butch Wonders. You needn’t be a lesbian — or even a woman, for that matter — to benefit from their sage advice.

So with that said, and before we dig into any of the entries proper, let’s talk a little bit — and by that I mean I’ll talk and you’ll have to listen or click a link somewhere else — about the journey from slob to suave, dumpy to dandy.

Early 1990s -- at least I had fantastic company
Early 1990s — at least I had fantastic company

My Dean Martin Awakening

I was in college when it hit me during a late night that involved a marathon of Matt Helm films starring Dean Martin and culminated in a pre-dawn viewing through bleary eyes of Mario Bava’s Danger! Diabolik — very possibly the experience that birthed Teleport City in general. I was, at the time, an impoverished punk rock college kid living on thirty or forty bucks a month, usually with disconnected power and phone in my one bedroom apartment in Gainesville, Florida. Until that night, youthful rebellion against “the suits” had led to my wardrobe being composed of a couple pairs of cut-off cargo pants, one pair of jeans, one pair of ratty black Chucks, and like fifty band shirts in varying degrees of disintegration. I cut my own hair — blindly and badly — had glasses that were bigger than my face, and clocked in at maybe right around 105 pounds and 5’7”. Which is to say not only was I (and still am) a nerd, I was a nerd with a body type that was, at the time, very difficult to clothe in anything that looked like it was actually made to fit me rather than something I stole from a much larger person’s wardrobe.

Plus, like many skinny kids, I was under the erroneous impression that wearing huge clothes made me look less skinny (they don’t, but we’ll get to that later in this series). Anyway, after a refined evening of watching Dean Martin slide ass-first down a railway whilst waving a ray gun over his head, I decided I wanted to start upping my style game. Less dumpster diving skate punk, more mod meets cocktail culture with a dash of rockabilly. I know, I know. Mods and rockabilly together? Impossible! But I live in America. We fought a war so we wouldn’t have to worry about whether or not mod and rocker goes together.

There were a few obstacles between me and my newfound desire to own a pair of wingtips and a slim-cut suit. First, as I mentioned, I was pretty broke. Not out on the streets and dying broke. Not four kids and no way to care for or feed them broke. I was broke punk rocker broke, which in the grand scheme of things, is a pretty manageable sort of broke, especially in a town like Gainesville where you could show up at the drop of a hat at any number of friends’ houses and be guaranteed a couch to sleep on and a sack of Taco Bell to tide you over until you got some cash. So I would not want to imply that these were dark and desperate times. I was just broke, as many twenty-year-old kids are. Certainly too broke to pop down to the local haberdashery to pick up a few new suits of clothing to match my new sartorial aspirations. That’s if we had a local haberdashery.

Even if I had the means, I did not have the vocabulary to express what I wanted. This was Gainesville, Florida, circa 1992. There was an Internet, but just barely, and only five people were on it. This was before fashion blogs, the dandy revival, and Queer Eye for the Straight Guy. It was hard to walk into a Sears or Old Navy with a picture of Sean Connery in Goldfinger and find what I was looking for. I did not know the words. What is that kind of suit called? What are those shoes? No idea. And the days of department store clerks being all Are You Being Served? was long gone. if I went to Dillards, I was not going to find John Inman and Captain Peacock waiting to take my hand and guide me through the morass and toward a better-dressed future. I was going to find some minimum-wage schlub who knew nothing, just like me.

Late 1990s: still not really getting it, but still in great company

The Journey Begins

So if there was going to be any success at all in my endeavor, the first step was going to have to be research. I did what I could, that really being nothing more than rifling through issues of Esquire at the bookstore. In the end, it all proved pretty discouraging. Nothing would fit me. Everything nice was hopelessly out of my price range, even if I relied on credit cards. And I still did not understand half of what I was reading. My aspiration of walking into a dressing room and walking back out looking exactly like James Coburn in the Flint movies ran headlong into an impenetrable wall of jargon, attitude, unavailability, and financial unattainability. I sighed, shrugged my shoulders, and doubled down on being a slob.

Time passed, and though I still harbored visions of transforming myself into a finger-snapping dapper lad, they were filed away deep at the back of my mind and buried under a dirt mound of assumed hopelessness. A move to North Carolina and my first grown-up job didn’t really help matters. My entry into the professional world of underpaid writing gigs was a chance to start anew, but I was still stymied by lack of funds, lack of shopping, and lack of knowledge. The work ensemble I put together was a motley Frankenstein’s monster of too-baggy Dockers that bordered on Hammer pants, a couple cheap, ill-fitting button-up shirts (I was still buying large despite barely being a small), and a couple ties I fished out of one of those donation banks at the mall.

When I moved to New York, I rekindled my interest in improved sartorial decisions. I was still low on cash, but at least now I was in a place with options. And we had the World Wide Web now, so I could start looking things up, learning the vocabulary that seemed so impenetrable to me before. Then Queer Eye hit, and suddenly everything was a lot easier, even on a tight budget like mine. So what emerged — and continues to be tweaked, improved, and improvised — is a mad concoction of jazz age dandy, mod, rockabilly, punk, and a dash of hippie in my old age. To abandon any one of those aspects of my personality and personal style would be to turn my back on part of who I am. And it is this background that I decided would make for an interesting take (I hope) on a style guide. We will start at the bottom and build our way up, operating always under the assumption that you, like me, are much more limited in your options than casual millionaires and fashion models.