Anniversary Shirts: 30 Matching Ideas for 1st, 10th, 25th and 50th Anniversaries

Anniversary shirts split into two: the ones the couple wears on the trip, and the ones the family wears at the 25th or 50th party. Both work best with a year on them. Here are 30 ideas by milestone, the format that looks like a real brand rather than a novelty, and how to size a pair you are buying as a gift.

The Est. format

Element	Example
Names or surname	"The Okafors"
Est.	"Est. 2001"
Milestone	"25 years"
Place	The city or the venue

Set it in vintage varsity or a badge and it reads like a shirt from a shop.

30 anniversary shirt ideas

First anniversary

1. "Year One: survived" with a tally mark
2. Wedding date in small serif on the chest of matching hoodies
3. "Still married" and "Still surprised"
4. A tiny illustration of the wedding venue

5th and 10th

5. "Est. 2016" in varsity block on both
6. "10 years, 0 refunds"
7. A cartoon of the couple then and now, one on each shirt
8. "Decade one" with a small roman numeral X
9. Your wedding song title in lower-case, no explanation

25th (silver)

10. "Silver Anniversary 2001–2026" in silver-grey print on charcoal
11. "25 years of him being wrong" and "25 years of letting her think that"
12. Family party shirts: "Team [Surname], 25 Years" for the kids and grandkids
13. A line-drawn portrait of the couple from their wedding photo
14. "Since 2001" as a small chest print for the trip

50th (golden)

15. "Golden Anniversary 1976–2026" in gold on navy
16. "50 years" in the style of a vintage concert poster listing the kids and grandkids as the line-up
17. Party shirts for the whole family with a cartoon of the couple in the centre
18. Caps for the grandkids: "Grandma and Grandpa's 50th"
19. The original wedding invitation redrawn as a graphic

Trips

20. "Anniversary Cruise 2026", see cruise shirts
21. Destination and year in passport-stamp style
22. "Second honeymoon" and "Third honeymoon" for the couple who counts

Funny

23. "Together since before phones had cameras"
24. "Still each other's plus one"
25. "Married my best friend. She's still not sure."
26. "Anniversary plan: same as every year, but I'll remember this time"

Quiet and nice

27. Both first names in one continuous script, split across two shirts
28. The coordinates of where you married
29. Two small rings drawn in one line
30. "Always" on one, "And then some" on the other

Sizing when the shirts are a gift

For a parents' anniversary, ask a sibling or check a label. Relaxed fits are safest: one size up on a tee, exact on a hoodie. See the size chart.

Party shirts for the family

For a 25th or 50th party, one design for everyone and each household orders its own sizes. No minimum, every size the same price. See family reunion shirts for handling a big group.

Making them

One sentence: "a vintage badge that says The Okafors, Est. 2001, 25 Years, Lagos to Manchester, silver grey on no background". The Wearlie designer makes it; order two, or twenty for the party. See matching hoodies for couples for the hoodie version.

Frequently asked questions

How much are anniversary shirts?

About $36 per tee and $48 per hoodie, shipping included, no minimum.

How far ahead should I order?

Four weeks; production and delivery takes two to four.

Can the two shirts say different things?

Yes, at no extra cost.