Teacher Appreciation Gift Ideas: Custom Photo Shirts for School Staff

Gift guide

Updated November 2, 2026

Teachers collect a lot of candles and gift cards every May. What they rarely get is something with a story attached. Picture a kindergarten teacher wearing her own kindergarten photo on the first day of school, or a principal walking the halls in a retro shot of himself at age seven. That’s the kind of present that gets talked about in the staff lounge. Below we’ve sorted our twelve teacher designs by where they teach, so you can go straight to the right grade.

Who it’s for

• Room parents collecting for one class gift in May
• Daycare families shopping daycare teacher gifts for the infant and toddler rooms
• Parents of a student on an IEP choosing special ed teacher gifts before the annual meeting
• Families comparing Pre K teacher gifts for the moving-up ceremony
• A grade-level team matching shirts for spirit week
• A spouse surprising a teacher on the first day back
• Staff thanking the principal during National Principals Month in October

Teacher appreciation gift ideas for preschool and kindergarten

Every design in this guide uses a vintage photo layout: one black-and-white picture under a tall headline in white or antique gold. For the littlest learners’ teachers, the joke writes itself, since the teacher’s own preschool picture usually looks a lot like the kids in her room.

First grade through middle school

Older kids are more likely to notice the shirt and tease their teacher about it, which is half the fun. Each of these is tied to a grade, so pick the one that matches the classroom door.

For SPED teachers, paras and the principal

Principal gift ideas are notoriously hard to come up with, and the aides and special education team often get overlooked in the end-of-year rush. A shirt solves both, because it’s personal without being too personal, and nobody else in the building will show up wearing the same thing.

More school designs are in these collections:

• Teacher Shirts
• Profession Shirts
• School Shirts
• Halloween Shirts
• Vintage Photo Shirts

Where to get the photo

Here’s the catch with any custom teacher gift: you need a picture, and students don’t usually have one of their teacher at age six. A few ways around it:

Whatever the source, it helps to know what prints well:

• Clear and well lit, with faces turned toward the camera.
• Phone shots and phone scans of old prints are fine; the higher the resolution, the sharper the shirt.
• No faces trimmed off at the edges.
• For photos of kids, keep it head-and-shoulders or waist-up, in everyday clothes. No swim, bath or leotard pictures.

We only print photos you own or have permission to use. School mascots that are trademarked, team logos, brand names, cartoon characters and famous faces can’t go on a shirt. If an order includes them, it’s canceled and you get a full refund.

How to order

1. Pick a garmentChoose tee, crewneck or hoodie and the teacher’s size.
2. Pick a shirt colorGo with something that suits the school colors or the teacher’s taste.
3. Personalize itUpload the photo and type the name. The sample picture on the listing gets swapped for yours.
4. Check outWe print it in the USA and send it with USPS tracking.

Which garment, which size

If you don’t know the teacher’s size, a relaxed tee one size up is the safest guess. Here’s what each garment offers:

Exact measurements are in our Comfort Colors size chart.

Timing for end-of-year gifts

For an end of year teacher gift or Teacher Appreciation Week in May, order early. Printing takes 1–3 business days and USPS shipping in the US takes another 3–5, so most packages arrive in 4–8 business days. We can’t promise a specific day, and school calendars don’t move, so give yourself a couple of weeks. See our shipping times guide for more.

Since the shirt is personalized, we can’t take returns for the wrong size or a change of mind. If it arrives misprinted or doesn’t match your order, send a photo within 15 days of delivery and we’ll replace it or refund you.

Teacher gift FAQ