Cover Of Book In Book Case

“I have given up on both belts and suspenders…I don’t mind suspenders, although I do tend to associate them with Wall Street wankers who wear comedy suspenders – somehow these fellows reek of desperation…The worst offense is wearing suspenders and a belt simultaneously. That’s what you call profound pessimism.” – Glenn O’Brien, How To Be A Man

Sadly, I never got to meet Glenn O’Brien, who passed away on April 7, 2017. He was one of my biggest idols as both a writer and a man of style and substance. Many pieces have been written (some by him) about his life as an artist, interviewer, film maker, and bon vivant. The role for which he will be most remembered, however, is likely that of The Style Guy.

Not bad for an Ohio-born kid who ended up living his life out in New York City.

For those of you who have been living under a rock since the year 2000 or are perhaps too young to remember (good God, how old am I??!?), The Style Guy was a column that started in Details and ended up in GQ in the early 2000s. Readers would write in with questions about all things sartorial and gentlemanly, such as:

  • When is the cutoff time for a morning coat versus a tuxedo?
  • What is a “military hem?”
  • How do you properly coordinate socks with an outfit?
  • Who pays on a blind date?
  • Is it ok to tuck a t-shirt into your jeans?

Not only were the questions answered beautifully (more on that below), the illustrations by Jean-Philippe Delhomme served as an excellent complement to O’Brien’s prose. Some examples are below:

Pencil Illustrations Of Various men

It was one of GQ’s most popular columns, and it was not the same after he left. In fact, he was none too pleased that they essentially muscled him out of his own column to try to make a “Style Guy 2.0” column. That said, I think it’s appropriate to remember him as The Style guy.

Glenn O’Brien Solved My Sartorial Conundrums

Back Cover Of Green Book

Back in fall of 2001, I was a freshman at college. My interest in menswear had taken root about two years before that, and I had already cultivated a reputation amongst my college friends as a guy who could dress himself.

The world was a less enlightened place than it is now regarding well-dressed men and their sexuality. These guys would crack gay jokes at my expense, seeing my garb as “a symptom of the gay gene,” to use a phrase Mr. O’Brien himself coined to describe such stupid comments.

They yukked it up until they had to get dressed for a class presentation or a date. At that point, I suddenly became a valued informational resource!


Reading Glenn’s column didn’t just give me the ammunition I needed to continue being helpful to my friends. It also gave me guidance in my own sartorial journey, which has turned out to be one of the most important elements of not just my career, but my entire personhood.

I only wish that I could have shaken his hand and thanked him for all he did for me without even knowing it.

My First Issue Of GQ

In the spring of 2002, I found myself in the school’s bookstore around final exam season. Needing a break from not studying (ahem), I noticed an issue of GQ that had a bodybuilder on the cover, along with the headline “Secrets of Aging Well.” I can boil that article down to three basic points from memory:

  • Don’t drink
  • Don’t smoke
  • Be happily married (emphasis my own)

I couldn’t tell you why aging well was of such concern to me as a 19-year-old, but it seems that it was. GQ was such a great publication back then! It had articles of substance, sound style advice, and was chock full of inspiration for budding menswear enthusiasts like myself.

Between my interest in the article and the fact that I’d wanted to subscribe to GQ for some time anyway, I bought the magazine. That’s when I got my first taste of The Style Guy.

The Style Guy’s Style

As it was many years ago, I don’t remember exactly which questions and answers were published. But the theme was the same every time: a man giving expert advice on subjects that were often out of the reach of the common man. He responded to questions that men were too embarrassed to ask each other due to a ludicrous fear of coming off as gay or effete.

Being of blue collar stock but having aspirational taste in clothing, I had a lot of questions about suits that no one in my social or family circles could answer. Glenn provided answers in an easygoing, witty, self-assured way that was, most importantly to me, non-judgmental. 

His writing was for anyone who was willing to take the time to read, and he was someone you really had to read. His writing required some brain power to digest. His time was before the Internet ruined our attention spans, and his expertise influenced countless blogs like Bespoke Unit.

It was in this vein that I wanted to find myself giving the advice that my friends -and, later in life, clients- desired. Dressing well shouldn’t be the exclusive dominion of the wealthy, well-connected, or well-born. It should be something anyone on any budget can do so long as they have the know-how and desire to do so.

Classic Style Guy Moments

Spine Of Book In Wooden Bookcase

Even the spine to How To Be A Man is written with witty eloquence.

Glenn answered many questions in his day. Some of my favorites are as follows:

“Who pays on a blind date?”

You do. The guy. Who did you think was going to pay? The person who set you up? It could be Dutch, but that idea would have to come from her.

“Are questions to Style Guy anonymous automatically, or should we state that we want to remain anonymous in our letter?”

As you can see, Kyle, readers’ letters are always printed anonymously.

“A wise person once told me a man shouldn’t buy himself a Rolex before he’s 30. Do you agree?”

I don’t agree. If you’ve just signed with the Yankees, or Grandpa kicked and left you his feedlot empire, why not buy yourself a Rolex? Sure, it’s a status symbol, but in today’s world of ridiculous watches it seems more sensible than showy. It’s the perfect survivalist watch, not needing batteries. It’s durable. And it may even appreciate in value. What shouldn’t a man do before he’s 30? I’d say getting married is probably a good thing to avoid in one’s youth. I don’t see what damage a Rolex can do to a fine young man.

The Best Advice You’ll Ever Read

One of the most common queries Glenn received was how to pair socks with trousers (or not), and apparently he gave some advice that a reader didn’t care for. This new reader wrote in something to the effect of the following, with the intent of making Mr. O’Brien appear to not know what he was talking about:

I suggest that you go to Bergdorf’s and ask one of their fashion consultants about color matching. They will tell you that your socks should match your pants.

Glenn’s response, which I memorized, was something like this:

Clothing does not have rules the way that golf has rules. It has principles based on aesthetics. If I’m going to the loan department at the bank, sure, I’ll likely wear gray socks with my gray suit, but if I’m going to the racetrack I might try to match my socks with the green in my tie. Right now I am wearing an orange shirt, khaki pants, and argyle socks with gray, brown, and tan in them. I am so happy with this combination, my ankles might explode. And I will certainly explode before I consult a consultant. This isn’t science; it’s art.”

If you take nothing else away from this article, or even your time reading this blog, let it be this:

This isn’t science. It’s art.

Sure, we talk a lot about color theory and other concepts that come off as rules. But it’s important to keep in mind that, as Glenn himself said, “Style isn’t fashion. Fashion is about what everybody’s doing, what everybody’s wearing. Style is about what you’re doing, what you’re wearing.”

The ultimate goal is to speak through your clothes and let yourself be expressed through them. Glenn O’Brien influenced many thousands of young men to do just that.

Rest in style, Mr. O’Brien.

Pencil Portrait Of Glenn O'Brien

About the Author:

Michael is a husband, father, clothes horse, musician, and Asian food enthusiast. When he's not blogging or changing diapers, he's playing bass guitar and singing in his Beatles tribute band.

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