T-Shirt Selling Strategy

I have been selling shirts for awhile, but started to get more serious about it. I figured I should document what my strategy is along with how things are turning out. Plus, doing this is more inline with my posting strategy on more complete posts. So I will cover everything for thinking up designs, actually creating the designs, getting them printed, selling channels, and marketing plan.

Design Ideas

The designs will be split into a few categories. The goal is to see which works better based on the time and cost to have the shirts designed compared to what actually sells.

The categories are:

  • Cartoon-style illustrated designs
  • Simple hobby/occupation designs
  • Text-only designs
  • Pre-made designs

Cartoon-Style Illustrated Designs

The idea here is that, while these designs will be more complicated to create, I will be more likely to be able to charge a premium for the shirt. The price point target is around $30 for these, which still might be too high.

I am not very good at illustrations, so these will be outsourced. This brings the added cost of paying someone else, but is almost no work after a designer is hired. However, this is now includes the risk of paying for designs that will never sell. Combined with the cost of ads, payment processor fees, and shipping costs, these must sell well in order to break even.

Simple Hobby/Occupation Designs

Simply hobby and occupation designs are mainly designs that I can find easy, targetable audiences on Facebook. They are more than just text, but not full-blown illustrations. The plan here to come up with some basic templates that relate to hobbies or occupations, and then use the template for multiple hobbies/occupations. That won’t work 100% of the time since a shirt about nursing might not translate well to an engineering shirt.

But the plan is to try to hammer out as many different targets as possible while not outsourcing the designs or spending a ton of time on them. This is primarily the quantity, strength in numbers game. The idea here is, with 5 to 10 shirts about a specific hobby, run ads targeting that hobby, and send them to the category page listing those shirts. Hopefully, the 5 to 10 are a wide enough range that the combination of the hobby and one of those designs will get a sale the majority of the time.

If they don’t, then screw it. That’s the whole point to make them simple, knowing some designs just won’t sell. Ideally, I can keep those to a minimum and only work on designs and hobbies that would sell. The only goal here is to try to get a few repeat or multi-item buyers. Since there will be several designs around a theme, maybe I can get 2 or 3 shirts sold to one person.

Text-Only Designs

These will likely be more on the lame side. Just text, nothing else, and nothing too fancy. These will be things like popular sayings, weird phrases, or stupid puns. The text won’t be various fonts with lines, polka dots, or any kind of extra visual enhancers. These will be things like “got milk?” with random things thrown in instead of milk…well, maybe not that design exactly.

This is similar to the above, where the goal is to puke out a lot of designs without spending too much time on them. The real reason to do this over the simply hobby designs is to see just how much the design really matters. Will a basic “Free Hugs” shirt written in a solid color Arial font perform better, worse, or exactly the same as a multi-color “Free Hugs” shirt with more of a cartoon font and some rainbows and unicorns?

Even if the latter does perform better, does it sell well enough to justify the extra work designing and printing the shirt? The text will be along the same lines as the hobbies, something that is easily targetable with Facebook ads.

Pre-Made Designs

These designs will fall into two categories. First, designs that someone else did that I will just have printed. Second, designs that are already done and printed; I would be getting the entire shirt. There are a lot of stock photo sites and other special marketing ebooks/guides that include complete, turnkey solutions to selling shirts.

The goal here is to see if the designs can really be sold. If they can, it could increase profit by not having to think of a design or hiring a designer. However, the designs are sold by more than one person making for tough competition.

The advantage of the already printed shirts is, I have nothing else to do other than ship the shirt. There’s no designing and no printing to either do or pay someone to do. Granted, I would have already paid for it when I bought the shirt.

The theory is, pushing out already printed shirts will be quicker and easy. Same day shipping would be an option, and the designs could include trademark or copyrights that are legally licensed and not just generic designs. Something I cannot do on my own or outsource. Even buying name brand shirts are an option, and it would make selling, especially on eBay and Amazon, easier. Theoretically, I could buy a name brand shirt and just sell it blank.

Getting the Designs

Using Amazon, eBay, and plain old Google, I will get some basic design ideas. Combined with targets in Facebook for ads, that will be the foundation of the shirt designs. For the easier ones, I will likely spend some time making the templates that I could then just fill in.

For the text based designs, the goal, if doable, is to make it more automated where I can feed in a list of phrases and have the designs created. Being that these are simple designs, once I can generate any string of text to a print-ready design, this should be possible to automate it.

For the illustrations, I will have to outsource those. I have a few ideas on the kind of illustrations I want, but really, anything that looks cool and can be sold, I will take. A lot of the “I will design a shirt for you” ads are more along the simple hobby designs that might use silhouette shapes and fancy text, but not real illustration. I will try to avoid paying for those, but I can’t avoid the hiring an illustrator.

Printing Options

There are a lot of reviews for Print On Demand services, which are usually fairly negative. Still, I will use Printful for some of the designs. The printing option will actually depend on the design. For the illustrations, I will have to use some kind of direct to garment printer, and I am liking Printful as I will talk about in the selling channels section below. Pre-made designs will also likely have to go with Printful.

Pre-made shirts clearly don’t need a printing option, and I will just mail out the shirt. This vastly simplifies the printing process, but greatly increases risk. I must now stock (or at the very least, find a drop shipper for the shirts) each design in each color in each size. I have been selling online long enough to know that there will be a design/color/size combination that will just not sell.

For the simple and text-only designs, I will be using a local print shop to print and ship out the shirts. There is slightly more work involved in doing this, but I feel that I can control the quality better. Also, the prices per shirt come out a whole lot cheaper. A basic t-shirt from Printful is $8.95. From the local place, it’s $4.50.

For some designs, I will actually step it up and go with the Printful custom labeling option. This will help build the brand. Again, the idea here is to test whether or not it’s acutely worth doing this.

Selling Channels

For selling, I am going to sell on a website I own along with eBay and Amazon. Using WooCommerce for the website, I can integrate directly with eBay and Amazon to push products to both. This way, I get the multi-channel selling without having to enter in products 3 times.

The big reason for picking Printful was it integrates with WooCommerce directly. This lets me create the products in Printful, push to WooCommerce, and then push from there to eBay and Amazon. The lite versions of the integration don’t allow for orders to be created on my site directly when items are sold elsewhere, but I am okay with starting off.

I am going with WooCommerce over Shopify and BigCommerce mainly because I want full control over the site. Additionally, I have hosting already and don’t want to pay extra to get the Shopify or BigCommerce sites up and running.

Depending on how this goes, I do plan on selling off a site complete with shirt designs. I haven’t yet decided if I wanted to go through the trouble of registering the brand with Amazon, though. If I do, that gives me the site, designs, and trademark to sell.

Marketing Plan

The obvious marketing plan is to advertise on Facebook. In addition, though, I would like to try some of the t-shirt showcase/product finder sites to see if any traffic from those sources would convert. I am also thinking about trying traffic from places like StumbleUpon and Reddit.

I don’t know if I can target well enough with anything other than Facebook, however. Additionally, Amazon ads might be tried to see just how effective they are. Really, I am betting that every sale will be a result from Facebook.


I will be taking shirt selling more seriously and try to it it consistently. I will branch out and try different methods and designs, and test what works and what works well. I will likely continue to update this post as time goes on with progress. At the time of the initial post, I have designs and am working on the websites for selling them. I will be using 2, maybe 3, different domains.


Here’s the first update, about 2 weeks into the plan.