Tuesday, April 10th, 2012

Dear Startup Boys: Tuck in Your Shirts for the Media

Say that Peter DaSilva is coming over to take your photograph. The San Francisco-based photographer has shot them all, from Ev Williams to Mark Hurd to Hunter Walk to Carol Bartz to, now, Mike Krieger and Kevin Systrom, the Instagram darlings of the moment, to accompany the front-page New York Times story about their sale to Facebook (for a billion in cash and stock, basically about a week after Instagram raised $50 million, at a $500 million valuation). And Peter's done it all without kicky filters! Tee hee! Anyway so of course maybe this photograph will end up on the front page of the New York Times and you didn't tuck in your shirt while Peter was there, and now you look unkempt, schlubby and not good in general. Even if you are a very handsome person, you will look that way!

I know that it feels square. I know that it feels like your dad's way to wear shirts. Maybe it's old thinking. Maybe it's inside the box, not even near the outside of the infamous box? And I know that sometimes you even forget a belt because you are so very busy! But before a photographer comes over, why don't you stop, look down and check yourself. Just say "Hey, give me five minutes." Maybe have one of the three women who work at Instagram come over and give you an honest opinion, if the culture there allows that? (Too scared to ask them? Then just ask Instagram engineer Philip McAllister, he's super-pretty.) Also, if you need a gay to take you shopping, lemme know.

It's okay, this isn't a big deal! People will take your photograph again later and you can correct this minor oversight in your business model.

57 Comments / Post A Comment

DoctorDisaster (#1,970)

Billionaires these days.

petejayhawk (#1,249)

@DoctorDisaster Pshaw, each of them is only a half-billionaire.

stuffisthings (#1,352)

@petejayhawk Dammit I was just about to say this!

Half-billionaires these days.

stuffisthings (#1,352)

Is one supposed to tuck shirts into one's jeans? That doesn't seem right to me.

lbf (#2,343)

@stuffisthings those shirts shouldn't go into jeans. But really, step 1 is "get a decent-looking dress shirt, goddammit, you're not sixteen and we're not on the set of a mid-90s MTV slackerxploitation proto-reality show". Then, surprise, whether your shirt is tucked or unticked is irrelevant, because hey, nice shirt, man.

lbf (#2,343)


@lbf "But I'm expressing myself!"

lbf (#2,343)

@My Number Is My Address that's what your soul patch is for.

@stuffisthings : I call this the "Jeans-and-Jacket Dilemma".

The situation is "I am going to a thing that is kind-of-but-not-totally-casual. I would like to look reasonably nice but not super-overdressed." THIS SITUATION HAPPENS ALL THE DAMN TIME.

There is a continuum from "super casual" (0 points) to "super formal" (10 points). We want a nice 6 or 7.

Workflow follows :
1. I am going to wear jeans, because dress slacks are too formal. My look is now "decidedly casual" (~4).
2. I am going to wear a dress shirt because a t-shirt is too casual. My look is now "right in the middle" (~5) and not formal enough.
3. I am going to wear a jacket because it makes me look like I'm making an effort. My look is now "just right" (~6 or ~7).

However, I am now wearing jeans, into which I must never tuck my shirt, and a jacket, which virtually necessitates I tuck in my shirt. So I look off-kilter even though my style is JUST RIGHT. It is a TOTAL STYLE CONUNDRUM.

Remarkably, this has plagued philosophers ever since Plato (who wore togas all the time).


stuffisthings (#1,352)

@Gef the Talking Mongoose This is why they make two types of collared, button-down shirts: one which is cut long and meant to be tucked in (the type the two 500-millionaires are wearing above) and another which is shorter and meant to be worn untucked. It's perfectly acceptable to wear the latter type untucked.

Also, you could probably get away with the shirt-jeans tuck if you're also wearing a jacket. Or just wear a more casual pair of trousers (perhaps something in corduroy?) THE OPTIONS ARE LIMITLESS! (Well, ok, actually still quite limited)

lbf (#2,343)

@stuffisthings good non-dad jeans will make your body look good with the shirt tucked; the only thing you need is a right-sized belt, neither dressy nor mexican-ranchero. You may end up looking like a Republican, a Gay, or both, though, but most dudes can totes rock that.

DoctorDisaster (#1,970)

The Dad Jeans question cuts right to the core of this issue. With a well-cut pair of jeans and a casual button-up that fits, you don't really need tucking if you're going for casual and hip. Loose-fit Wranglers from Belk and a long floppy dull-colored shirt? Casual becomes sloppy and hip becomes HA HA HA HA HA

jolie (#16)

Look it's not that I don't appreciate that The Awl is here to address the important issues of our times (not sarcasm, truly) but would it have killed you to also suggest that they WASH THEIR FUCKING JEANS OH MY GOD THOSE THINGS LOOK LIKE THEY CAN STAND UPRIGHT ON THEIR OWN EEEW EEEW EEEW.

Lockheed Ventura (#5,536)

@jolie They closed a 50 Million Dollar financing round LAST WEEK and announced a Billion Dollar acquisition this week. They have likely been sleeping under their desks if they have had any sleep at all during the past world wind week. Wrinkled jeans and untucked shirts are the last thing on their minds.

jolie (#16)

@Lockheed Ventura Well then they could certainly have paid someone to launder their dungarees.

melis (#1,854)

or they could have had those dad jeans quietly and efficiently destroyed

dad jeans

Moxie (#81,363)

@jolie Get rid of your schlubby jeans, they're revolting.

laurel (#4,035)

@Lockheed Ventura Ah, 'world wind' week. So internationally blustery.

DoctorDisaster (#1,970)


Nick Douglas (#7,095)

Couldn't they just spring for some better-fitting shirts, and the short-tailed kind that was made for those of us who refuse to tuck?

Cause tucking in those shirts would look a little… Seinfeldy.

stuffisthings (#1,352)

@Nick Douglas Yeah I was waiting for Choire to suggest a woven belt too.

Brian (#115)

@Nick Douglas Seinfeld looks like Cary Grant next to these two.

Tyler Coates (#451)

At least they're not wearing shorts?

City_Dater (#2,500)

@Tyler Coates

Let's send the photographer back in three months and see what he finds. (Jorts!)

Bittersweet (#765)

@City_Dater: Jorts look better when you use that 70s-style setting.

Aloysius (#1,808)

What do guys like that do with a half billion dollars? How many Playstations does one person need?

deepomega (#1,720)

@Aloysius Do you have any idea how much money it costs to cover every inch of wall and ceiling with skateboard decks?

boyofdestiny (#1,243)

The first thing I would do with that money is buy a larger room. They look cramped.

DoctorDisaster (#1,970)

@boyofdestiny That's the photographer. They also appear to be standing on a cushion. "Hey guys could you cram yourselves into the corner of the room and stand on that bench? Awesome. Now I can fill up the frame with these pretty window things instead of your HIDEOUS DAD JEANS

max bread (#5,970)

Not that I don't agree in spirit, but tucking those shirts into those jeans isn't going to make them look presentable.

Lockheed Ventura (#5,536)

"And the bitter underminers, well, they're too obvious to even worry about. OMG they're going to make fun of you on their Tumblr!? That's okay. They are just frustrated. Be nice to them, they can get better with time, because eventually most of them realize that composing nasty emails about people they don't really know to their friends all day has been a waste of their energies. Some of these people turn out great actually!"

jolie (#16)

@Lockheed Ventura Cunty! I like it. But fair warning: Choire's probably going to block you on Twitter for that.

Multiphasic (#411)

@Lockheed Ventura Thank god there's someone still willing to speak for the voiceless, beleaguered millionaires.

hockeymom (#143)

Primrose Everdeen didn't tuck in her shirt and look what happened to her.

Can we also talk posture? Sit/stand up straight like you are not the "before" image of Deenie? You will look 10 lbs thinner and your back (particularly that little bit behind the shoulder blades that gets twinge-y from working on the computer) will thank you.

C_Webb (#855)

@Newly Recently Redundant DEENIE OMG.

Half bazillion or not, just not fuckable.


@Clarence Rosario Oh, wait, they went to Stanford. Nothing's going to help.

Who cares how they dress? The important thing is they manufact in abundance the carbon-cured steels that go into the dreadnoughts that keep the kaiser's porky fingers off our beloved Philippines. Huh, what? Wacky filters for digital pictures? Okay, I see. Well then, fuck 'em if they can't tie a tie.

hman (#53)

Startup Boys is a terrible name for a band.

Bittersweet (#765)

@hman: Dad Jeans is pretty good, though.

lempha (#581)

Their shirts don't fit them tho. Look how far down bro on the right's arm the shoulder seem on his shirt goes. They could tuck all they want and still look a mess.

hockeymom (#143)

Here's a question about Instagram….who uses it besides my 11 year old daughter and all of her friends? It's the weirdest thing.
They post all sorts of "arty" photos, then take shots of all their "likes" and post that, too.

Over spring break, it was a super passive-aggressive way to neg on the kids who didn't go anywhere warm. Not sure that was the intent, but it quickly became a record of who went to Costa Rica and swung through the mountain tops on a wire, and who posted desperately having fun photos from their "staycation" in the burbs.
(Not REALLY trolling on the 11yr old…she uses my phone to post pics because I'm super mean and won't get her an iPhone like "everyone else")

deepomega (#1,720)

@hockeymom Everyone I know between the ages of 15 and 40 uses it as a photo sharing ecosystem. Oddly, I think part of the appeal is "it's not facebook" so we'll see what happens now.

Mr. B (#10,093)

@hockeymom I associate Instagram with the mommies in my Facebook feed who post sepia-toned images of their toddlers doing ostensibly cute things 20 times a day.

@deepomega Exactly: I use it with my friends as a visual quasi-twitter. I don't care what the Google behemoth knows about me – they ain't letting the public search my emails – but I don't trust Zuckerberg's scrawny ass as far as I could drop-kick it.

deepomega (#1,720)

Have you considered making a pinterest styleboard as a guideline for them?

hockeymom (#143)

@deepomega I am liking, uploading and pinning this comment.

LondonLee (#922)

As the (former, I got laid off few weeks ago) art director of a Tech magazine I was continually depressed at the lack of style shown by these young whiz kids. But at least they're not hungover unlike a certain someone we shot for my last issue.

Matt (#26)

What is this, The Billfold?

NO NO NO NO NO….do not tuck in your shirt! You will NOT bring your brickandmortar values over into my Internet.

Belt? Yes.

Tucked in shirt? Really? No, just no.

@Jason Benjamin McKinnon@facebook : Technically, it's not your Internet; if you read your introductory literature, you'd know that the Internet actually belongs to commenter numbers between 3,001 and 3,500.

It's in the Commenter Number and Associated Birthright chart.

0 – 200 : Overweening pride
201 – 500 : Envy
501 – 1000 : Grammar skills
1001 – 1500 : A nice leather-bound day planner
1501 – 2000 : A mess of pottage (shared)
2001 – 2500 : The tragedy of the commons
2501 – 3000 : Three flavors of popcorn in a commemorative can
3001 – 3500 : The Internet
3501 – 4000 : The right to wear shorts
4001 – 4500 : Special edition "Labyrinth" DVD
5000 – 5500 : Mystery birthright! (actually herpes)
5501 – 6000 : The ability to remain unmoved by cat videos
6001 – 6500 : A decent haircut
6501 – 7000 : Complete shoe-cleaning kit
7001 – 7500 : Beatboxing skills
7501 – 8000 : The ability to name types of plaid
8001 – 8500 : Natural rhythm
8501 – 9000 : A shoebox of death metal mixtapes c. 1993
9001 – 9500 : A really good pocketknife
9501 – 10000 : Novelty book of tear-out "parking tickets"
10001 – above : Perspective, and a two-for-one Capri Sun coupon

Brunhilde (#1,225)

@Gef the Talking Mongoose: I registered too early, I really want that DVD!

@Gef the Talking Mongoose God I wish I'd thought of that.

Bittersweet (#765)

@Gef the Talking Mongoose: No grammar errors in your comment, dang it.

Jay (#10,046)

Is it really so bad that I should have noticed without guidance?

I'm doomed.

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