I think good merchandise, whether free or paid is critical to have at a conference. Every time you print a t-shirt or create a sticker you're making an advertising investment in hopes that someone will put that sticker on their laptop or wear the t-shirt and it will be recognized. Would you half-ass a commercial, radio ad, or print ad? No way! You'd want to make sure it was something you could be proud of, and in the grand scheme of things merchandise is on the cheaper end of this spectrum. So what makes good merchandise? Let's look at some great items I've been given over the past few years.
In October of 2013 I attended DevOpsDays Atlanta. They had an assortment of t-shirts and other goods from companies that were sponsoring the event. I try to keep my acquisition of things like bags, pens, and other items to a minimum since most of these handouts are poorly made and relatively pointless. The only exceptions to this rule are t-shirts and stickers. Most of the t-shirts I get just sit in my closet because they either don't fit well, are made from extremely cheap shirts, or have embarrassing phrases on them that scream 'I am a nerd and better than you'.
None of these things make me want to wear a t-shirt, so when I went to DevOpsDay Atlanta and saw these (http://instagram.com/p/QYld7mMzGJ/) t-shirts. I was pretty impressed. Let's start with the most important thing, the shirt cost more than 20 cents, and wasn't made by some Honduran child in a sweatshop. In fact they sprung for American Apparel, which is a win in my book as a tall skinny guy. The shirts are long enough where I can raise my arms above my head and not go 'oh look my belly button!'. The design on the front is also really interesting, and doesn't scream IT. The actual product (Mandrill) is a tiny logo near the bottom of the shirt on the back. It isn't the main focus, instead this really cool design is and I appreciate that. I like this shirt so much in fact that it's part of my conference roster of t-shirts. If I've got to travel somewhere for a conference this shirt goes with me, and I wear it almost every week anyways since it's so comfortable and fits well. I get complimented on the shirt and the awesome design on a regular basis by people who aren't in the IT world.
Another great example is the hoodie I received from speaking at SeaGL, these guys have a great logo, and they kept it simple. A comfortable (American Apparel again here) zip up hoodie, with the logo on it (https://twitter.com/osuosl/status/526776280369225730), and that's it. It's simple, it looks good, and the hoodie is comfortable. What more could you want?
I've received shirts that have embarrassing phrases, are printed on shirts that were on sale because they are a gross color, or are really uncomfortable due to the quality of the shirt. Guess what? These shirts don't leave my closet and are the first to be donated. They don't make me look good, so why would I want to give the company that provided them free advertising?
If you aren't thinking of your t-shirts as an investment into the people who love your software or respect your company then you are doing things wrong. Don't cut corners on t-shirts, and don't create designs which scream 'I am better than everyone else'. If it's just your logo that's fine. A high quality and comfortable shirt or hoodie goes a long way towards being worn on a regular basis. If you can't say that you would wear this shirt every day, then why print it? Would you pay for this shirt if you could? If not, think about what makes it that way and fix it. Whether it's an extra 2 dollars per shirt to get a nicer shirt, or another run through the art team's hands.
If I can see the pride your organization puts into something as simple as a t-shirt, then I can't wait to see what you do when it comes to a real product.