How to Order Matching Shirts for a Big Group (Without the Stress)
Twenty people, twenty sizes, one deadline. Here's a simple timeline and checklist for ordering matching shirts for a big group — and keeping your sanity.
By the MatchingTee team4 min read

Matching shirts for a big group look effortless in the photo. Behind the scenes, someone collected twenty sizes, chased six late replies and double-checked the spelling of every cousin's name. If that someone is you, this guide is for you.
Here's a simple timeline, a spreadsheet template and the tricks that keep group orders calm.
The four-week timeline
Work back from your event date:
| When | What to do |
|---|---|
| 4 weeks before | Choose the design and announce the plan |
| 3 weeks before | Collect names, styles, sizes and colors |
| 2–3 weeks before | Chase stragglers, then place the order |
| 1–2 weeks before | Shirts arrive — check them and sort them |
| Event day | Hand them out and take the photo |
Most orders are made and handed to the carrier within 1–2 business days, and delivery usually takes 2–6 business days within the US. Four weeks gives you room for the one relative who replies late — there's always one.
Step 1: Pick one design everyone can live with
Choosing a design by committee can take longer than everything else combined. To keep it quick:
- Shortlist three designs yourself, then let the group vote.
- Set a voting deadline — two or three days is plenty.
- Choose designs with personalization. When each shirt carries a name or its own line, people care less about the design itself.
For ideas, see our guides to family reunion shirts, cruise shirts and girls trip shirts.
Step 2: Collect everything in one place
A group chat is where sizes go to die. Instead, make one shared list — a spreadsheet or a simple form — with these columns:
| Name to print | Style | Size | Color | Paid? |
|---|---|---|---|---|
| Grandma Rose | Women's V-neck | L | Red | Yes |
| Uncle Tony | Adult unisex | 2XL | Black | No |
| Mia | Youth | M | Red | Yes |
A few rules make this list reliable:
- Ask for the name exactly as it should be printed. Nicknames, spelling and capitalization included.
- Ask for the style, not just the size. A "medium" means very different things in adult, women's V-neck and youth.
- Point everyone to the size guide and suggest they measure a shirt that already fits.
- One person enters the order. Fewer hands, fewer mistakes.
Step 3: Handle the money simply
If people are paying for their own shirts, decide how before you order:
- Collect before you order, not after. It's much easier to chase a payment when the shirt doesn't exist yet.
- Use one method — whichever payment app your group already uses — and note payments in your list.
- Round up slightly to cover shipping or a spare shirt, and settle up afterwards.
Step 4: Personalize and check every shirt
Enter each shirt from your list in the customizer: style, size, color and name. Then:
- Check the preview every time. It shows exactly how the name sits on the shirt.
- Read names out loud against your list. A missing letter is the most common group-order mistake.
- Count the cart against the number of rows in your list before you check out.
We print exactly what is submitted, so this is the step where a little care saves the most trouble.
Step 5: Late joiners and spares
Someone will join late. Decide in advance whether you'll place a second small order or close the list. If budget allows, ordering one or two spare shirts in common sizes — personalized with the group name instead of a person's name — can rescue a last-minute guest.
Step 6: Sort and hand out
When the shirts arrive, check each one against your list, then sort them into bags by household, labeled with names. At the event, hand out the bags early so everyone is dressed before the group photo — not halfway through the party.
Very large groups
For reunions, schools, teams or company events with a large headcount, email us at info@matchingtee.com before you order with your design, rough quantities and event date. We'll help you plan the order and the timing. Our group orders page has more details.
The checklist
- Design chosen and announced
- One shared list with name, style, size, color and payment
- Everyone pointed to the size guide
- Payments collected
- Every shirt previewed and checked against the list
- Ordered at least two weeks before the event
- Shirts sorted into labeled bags
Follow that, and the hardest part of the day will be getting everyone to look at the camera at the same time.
Frequently asked questions
Is there a minimum order for matching shirts?
Can everyone in the group have a different name and size?
How early should I order shirts for a group event?
Shop the look
Family Reunion designs to personalize
Round Tree Family Reunion 2026 Shirt
FromOriginal price $21.29Sale price $14.90
Family Reunion 2026 Shirt
FromOriginal price $21.29Sale price $14.90
Wide Tree Family Reunion 2026 Shirt
FromOriginal price $21.29Sale price $14.90
Family Reunion 2026 Shirt
FromOriginal price $21.29Sale price $14.90
Written by the MatchingTee team
We design, print, embroider and pack every order at our studio in Stafford, Texas, and we write about what we learn from helping families and groups match. Questions? Email info@matchingtee.com.
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