When I was 22 or thereabouts, I used to read The Diaries of Franz Kafka at the beach in the hope of being noticed reading the diaries of Franz Kafka at the beach. Furthermore I used to wear a women’s leopard-skin faux-fur coat to clubs where I would smoke clove cigarettes and pretend to be uninterested in everything and everyone. If it had been light enough to see, I probably would have read The Diaries of Franz Kafka there too. In my defense, It was 1991, I was completing a Master’s Degree in English Literature, and being a complete twat about it. What’s the most pretentious thing you used to do?
Mid-late 70’s, I used to walk around with a classical guitar slung over my shoulder.
I also used to hang out at the State Library, reading all sorts of tomes about education especially alternative education (big thing back then).
One day I was exiting the library after a reading session, and my guitar fell from my shoulder, snapping the neck in two.
I wasn’t quite so pretentious after that. 
I had a cigarette case for my clove cigarettes.
Another English major here. 
I used to smoke Black Sobranie cigarettes. If I was still a smoker, I think I’d enjoy doing so to this day.
Oh, God, you’ve just reminded me. I had one of those too, only it was an old one which was too small for modern cigarettes so I used to cut down perfectly good smokes to fit inside.
Good lord, so many things. Sigh.
Remember Jack Black’s character in High Fidelity? The music store loser who was sneeringly condescending to customers whose taste he didn’t like?
I had too much of that guy in me. I would try to find the perfect artist - music, art, actor, whatever - to hate in order to disrupt people. “Renoir Sucks!” was a favorite (to be clear, I think there is an argument to be made that Renoir was not at the same level as folks like Monet and Manet, but blurting out Renoir Sucks is not the way to have a thoughtful discussion).
And yes, sometimes I made statements like this while wearing leather pants. To be clear: A man in the 2.6% of men who can make leather pants work is a badass. I am not one of those men.
I went through a phase for several years in my mid thirties where I would wear a cravat, socially and instead of a necktie to work.
I still have some of the cravats; they’re beautiful and I look at them occasionally to remind myself of just how badly wrong my judgment can be.
Wore an ascot? In high school yet. I don’t know why I didn’t get beaten up.
In my early 20’s I smoked a pipe for a while. I had to be careful because it had a tendency to make me queasy if I overdid it. One of my pipes was a calabash and meerschaum Sherlock Holmes pipe, which I tried very hard to get to be the right mellow color, but never really succeeded. (This was only pretentious because I didn’t particularly enjoy smoking a pipe or anything else, I just liked the way it looked.)
Under “used to” I would say smoking straights with a cigarette holder and using the word “albeit” often in casual conversation (long before The Master made it popular to do so). One I’m still guilty of is using mostly fountain pens; packing one around with me most of the time rather than the usual disposable pen.
I definitely did the read “impressive” books in public hoping to be noticed. It never worked, and the kindle has largely removed this option anyway!
Early in college, when I came back during a break to hang out with high school friends, I went to pick them up, and had some classical music teed up to a specific part that I had familiarized myself with in order to pretend that I knew a lot about classical music.
Million dollar idea: e-readers with a screen on the other side to display your pretentious book cover. Heck, it doesn’t even have to be the same book! It could be displaying “Catcher in the Rye” while you’re consuming some beach novel spy thriller.
21 year old me would have bought this gladly.
Pretension is something that I loathe, but since I had some of it myself, I can sort of forgive below a certain age. Say, 25 years old. Above that, and it’s getting sad.
I’m curious, to be noticed by what kind of people? Sounds like you made yourself unapproachable. Were you hoping someone was going to work hard at pestering you until you finally talked with them?
What’s up with the clove cigarettes? I don’t get the reference. Was some famous writer posed smoking them on a book cover?
I Used To Capitalize The First Letter Of Every Word I Wrote.
It’s a way to been seen smoking, without actually smoking tobacco and risking addiction. They’re not particularly enjoyable, so it marks someone as smoking for the benefit of others’ eyes.
Clove cigarettes (kreteks) do contain tobacco, and are often higher in nicotine than standard American brands.
Ignorance fought! Thank you for the info.
My most pretentious moment: Used to wear a sport coat to high school. To be fair it was a private school, but the only other student to wear one was my best friend. We did look a bit like the douche twins.
I did a little googling and it appears that “clove” is also becoming a synonym for “herbal” cigarettes. Looks like I’m not the only one who is misinformed.