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All my life, there have been certain things I've wanted but never owned. It hasn't been due to expense or illegality (with the exception of that one mail-order sex robot I saw). Instead, I felt that I just wasn't cool enough to use these things. Often, they belonged to some other time. It was no longer something that everyone had, so owning it now just felt like an act of trying too hard. I couldn't pull it off without feeling self-conscious.

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No, not things like this. I can pull off leather chaps easy.

Now, that might sound like a lack of self-esteem, but it's really not, because in truth I think most people aren't cool enough to own these things. They belong to another period, another spirit, and if you disrespect that and drag them kicking and screaming into your time and place, you won't be fooling anyone.

6
Fedora

Man oh man. I have always wanted to wear a fedora. And why wouldn't I? When I think fedora, I think Indiana Jones. I think Mad Men. I think a man at a bar with a whiskey and a cigarette.


Note, that even in a graphic for my video series, I couldn't actually put my face in it.

The longing for the elegance and masculinity of the fedora is real, but the realization of wearing one in the 21st century as being the act of poseur is even stronger. That's why even in my novel, where the protagonist shares my name, I could hardly bear to let him wear a fedora. First, I made it his grandfather's, and then I had his best friend call him a "hipster douchebag" the rest of the book for doing it.

The problem is, while I want to wear a fedora, I don't want to be the dude standing out in a fedora. I have no intention of the world saying, "Hey, check out the dude in a fedora!" It's more wanting to be part of a time when you could wear one without anyone caring.

Who Can Get Away With It?

Jon Hamm while he's in character and on the set of Mad Men. No one else. Sorry Hipsters. You suck.

5
Flask

Ah, the flask. Y'know the kind I mean, right? A real one like this:

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OMG, I want to be drunk right now.

The reason I've never bought a flask is I don't know how to use one. Sure I could buy one. Hell, I could buy a whole bunch and keep them on a shelf like a quaint little alcoholic version of a Hummel collection. But why would you do that?

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These are not good to drink out of.

No, when I say I want a flask, that means I want to wake up every morning, fill it with whiskey, put it inside my jacket pocket, and take a pull whenever I damn well please. But there's a word for people who do that: alcoholic. The world does not let you surreptitiously carry liquor and then publicly consume it.

So, yeah, I know people who bought flasks, and they have them, and maybe sometimes they go to a picnic or feel like getting drunk in a movie theater. So they bring the flask. But I don't see the point of that. I pack the bottle for the picnic, and I haven't snuck booze into a movie theater since, well, I guess I never did that. Here's the deal: I want to live in the world, get some bad news, and then reach for my flask and say something like, "Looks like I'm going to need this," and take my pull. And if I can't do that (and I can't, because that would be the sign of a serious drinking problem) then I don't want the flask.

Of course, a flask is another thing from this list that I gave to my character in Notes from the Internet Apocalypse, but that was sort of the point. Not that he was cool enough to do it, but because he did have a serious drinking problem. so many problems.

Who Can Get Away With It?

Eccentric millionaires or the unemployed. No one with a boss or a business to run.

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4
Fingerless Gloves

Not every burning purchasing desire of mine is born of a need to look like the lead in some black-and-white noir thriller. For example, I really like fingerless gloves. They look really cool.

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Um, not in this context. Getty Images, you have failed me.

That pic is ridiculous. You would never want fingerless gloves in the snow. That's stupid. If you wore fingerless gloves in the snow, you'd get frostbite and lose your fingers and then those gloves would fit perfectly. Fingerless gloves are good for when it's cold but not that cold and you need use of your fingertips to do something: count money and/or smoke. That's about it. I guess, though, they're good for one more thing according to Getty Images. Whatever this is:

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Is this porn? And why did it come up during a search for "fingerless gloves"?

Actually, the 21st century has given us one more reason for fingerless gloves: touch screens. But now they make those fancy gloves with bio-sensors in the fingertips, which are actually less douchey to own than fingerless gloves.

Who Can Get Away With It?

Carnies, who have a job that requires they stand outside in the cold and still collect money and tickets.

3
Old-Fashioned Camera

I have to admit this next one doesn't apply to me. But I can relate to it. Have you noticed there seems to be an in ordinate number of quirky, attractive women who claim they're "photographers"? Like, they may or may not actually be a photographer. Good chance no one's paying them, but the thing that makes them a photographer is they have a nice, old-timey, non-digital camera, like this:

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It takes this thing called ... "film"?

Why do they have this camera? Are their skills beyond their phone's cam? If yes, are they beyond a quality digital camera? Pretty sure these questions were neither asked nor answered. I'm sure there are professional photographers, many even, who still use traditional cameras and develop their own images, and that's fine, but I'm even more sure there are people out there (dudes too, I guess, but I seem to see it less) who are just getting off on carrying around their "vintage" cam on a strap as the world's most validating vintage necklace.

Who Can Get Away With It?

A photographer who has used one since before their were digital options, better still if they're an actual photographer.

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2
Smith Corona Typewriter

As a writer who's already shown an attraction to the items of the past, I guess you're not finding this one too surprising, but the desire for this typewriter never held much allure to me. Don't get me wrong. I've wanted to own them. I love the look of them, but I got it out of my system. As a kid, my parents let me tool around on some old typewriters we had in the basement. My grandfather's old typewriter was a nice one. It was a lot of fun to see the mallets strike the paper and beat ink out of the super old, dry ribbon, but my compositions looked like crappy ransom notes and it was hard as hell.

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Like Madonna in her prime: sexy as hell, but almost impossible to use without complications.

My brother has an electric typewriter. I needed to type up some more formal things, so I used it, and it sure was easier. By the time I was in high school word processors existed but weren't all that common, and I used my other brother's even more superior electric typewriter for my college applications. That machine had the Correcto-Type built right into the unit.

Then I started college with a word processor that looked like a toaster oven but was even better for typing. And by the end of college, I had a full-blown computer with a word-processing program and everything. The point is, trust me, I get it. I love everything about the look and style of the old typewriters but know they are inferior in every way. Whenever I saw idiosyncratic individuals using one for their college papers or, unfortunately, their novels, I knew it was indisputable proof of sheer pretension.

Who Can Get Away With It?

The ghost of Raymond Chandler.

1
Pocket Watch on a Chain

At this point, you've probably noticed a theme here. Maybe not, because, frankly, it wasn't until I started writing that I saw it. Just about all these things are things I've seen as a child that were no longer in fashion as I reached adulthood. Indeed, some were no longer in fashion when I was a child. Or even 50 years before that. But this one is a classic.

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A device that seems to control time as much as tell it.

There is something almost magical about pocket watch on a chain. Whether it was the dad's watch in Mary Poppins or Burgess Meredith's watch that could stop time on The Twilight Zone, I loved the ritual of it. You remove it from your pocket, give it a flick, check it, close it, and return it to that tiny vest pocket. Much cooler than just looking at your wrist or phone.

And there, again. Notice another trend? A suit. A suit ties so much of this together. You can wear a fedora without a suit, but you'd look like some hipster douchebag. You can carry a flask without a suit pocket to slip it into, but then you're just opting to use a suit-shaped cup without the suit for some reason. And I guess you could carry a pocket watch on a chain without the suit, but then you'd just be a weirdo. How do I know? Because I did that one in college.

It wasn't a nice watch. In fact, I saw it for sale for, like, $20 at a Kmart, and my real watch had just broken. I clipped it to my jeans belt loop and kept it in my pocket and felt like a douche every single time I checked the time. And because it was a piece of crap, it fell apart in a month and no one ever needed to know more about it. But I can't lie to you. We've shared too much.

Who Can Get Away With It?

Your 80-year-old uncle from England who still toasts with "God save the queen!"



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