by Joshua Baer

Many of the startup t-shirts I see are completely worthless — no one is going to wear them who doesn’t get paid to.

They are ugly and uncomfortable. When looking through my closet, I’ll never pick that shirt over another one that is more comfortable or has a meaningful design that I connect with emotionally.

An entrepreneur’s most common initial reaction to the t-shirt and swag question is to spend as little as possible. After all, it’s hard to go wrong with frugality.

But t-shirts come from the marketing budget and should be optimized like any other spend. Done properly, one shirt can deliver tens of thousands of impressions worth thousands of dollars. Done poorly, they will just get thrown in the trash and never worn — worth pretty much zero.

The cheapest shirt you can buy will run $3 or $4 each in volume. A really nice shirt will be $7 or $8. The $3 shirt is mostly worthless and the $7 shirt can be priceless.

Start with the best material you can find

My shirt of choice these days is by Canvas, but other good brands include Pima, Next Level, and of course American Apparel. My favorite for softness is the tri-blend 50% Polyester, 25% Cotton, 25% Rayon.

In general, go with the softest, thinnest t-shirt you can find. Make sure it comes with a tear-off tag.

I’m always on the search for next best t-shirt. If I find something I like, I take a picture of the label or bring a sample to my t-shirt supplier and usually they can find the exact same material or something really close.

It’s worth spending more on a nicer shirt because I’ve found that the t-shirt quality is the most important factor in whether or not people keep it and wear it over and over.

You want this to be the shirt that your girlfriend or boyfriend steals to sleep in because it’s so comfy — think of what a branding win that is right there.

Create a design that people want to wear

You want the shirt to be striking enough to grab people’s attention but not so striking that people feel self-conscious about wearing it. A bright, neon color with an obnoxious logo and slogan might make your VP of Marketing get excited but it won’t be interesting to most other people.

Think about whether someone who didn’t even know what your company did would want to wear this t-shirt?

Here are some tips for a great design:

A simple logo is always good — as long as your logo is good. When in doubt, your first t-shirt should just be your logo centered on the front chest. I never really understood why, but everyone loved the logo shirt for OtherInbox, my last startup. I would be walking through a random hotel in NYC and the bellhop would say, “Nice shirt!” It was easy to get people to wear them.
Your company slogan is probably not as clever to everyone else as it is to you. Writing on your shirt should be funny, relevant, ironic, insightful — it has to be so good that someone who doesn’t work for your company would want to wear it. A great example is this Google for Entrepreneurs t-shirt that says, “Always Work Hard on Something Uncomfortably Exciting.”
Nobody wants to wear a shirt with 10 company logos on it except maybe for a marathon where it feels cool to be sponsored like a race car. Stick with one big logo and maybe two or three supporting ones if needed. Use the sleeves for additional logo locations to keep it from getting too busy.
Put the year somewhere on the design — it can be prominent or hidden. Brett Hurt taught me to always put the year somewhere on the shirt so that you can tell one shirt from another. It will become a source of pride to have one of the originial t-shirts, especially when you make shirts that last forever (see below). I like hiding it in the design like an easter egg.
Pay to have a designer make something special for you. Even if you don’t have this talent on your team, every t-shirt shop has their own in-house designers who just make t-shirts all day long and are really good at it. Write up or sketch up some ideas and send it to them and for a few hundred dollars they will make a custom design for you that blows your mind. I use Outhouse Designs in Austin, Texas.
Don’t choose white shirts. They are hard to pull off well. People seem to like black shirts and colored shirts better. Personally, I think white shirts make me look fat. Jason Cohen points out that dark shirts don’t get as dirty and aren’t see through when they are wet.
Don’t use thick layers of ink. Big patches of thick ink on the shirt make it really uncomfortable to wear. of course, if you use discharge printing (see below) this is a complete non-issue.
Use discharge printing so that it lasts forever
This requires a 100% ringspun cotton shirt (I use the one from Canvas). The shirt costs the same but the ink process costs $1 extra per shirt.
The default printing method lays the ink on top of the shirt. It starts washing off after 5 or 10 times through the washing machine.
If you use discharge printing, it actually dyes the shirt so that it never washes out. This is the kind of shirt you’ll still be wearing 10 years later.
How many should I make of each size?
Every group is different, but here is a spreadsheet that I use to calculate how many shirts of each size I should order. Every time I order I tweak the numbers a little bit based on how many are leftover. You just enter the total number of shirts you want to order in the top cell of column B, and then adjust the other percentages in column B as you see fit. You can download that spreadsheet and modify it for your own use.
Don’t just order Men’s cut or unisex shirts. Women don’t like those and often won’t wear them. Order some in a Women’s cut and you’ll be sure to impress the ladies in your audience.
Bonus trick
Get crew-necks for all of the men’s shirts and v-necks for the women’s shirts. It makes it much easier to tell them apart when they inevitably end up in a big pile. You can also use color to differentiate them.
Some Examples