Most anniversary gift lists are ranked by price. That is the least useful axis there is. Here is the same question ranked by the only thing that turns out to matter: how long it goes on meaning something.
Lasts about an evening
Aftershave. A bottle of something good. A meal out that neither of you will describe in detail a year later. None of this is a mistake — an evening is a perfectly respectable thing to give someone. Just do not expect it to carry the weight of the occasion on its own, and do not be surprised when next year's version feels like a repeat.
Lasts a season
Clothes, watches, gadgets, the nice version of a thing he already owns. These live longer, but they drift: within a few months the object stops being the anniversary present and becomes simply his coat. That is not failure. It is just what objects do — they get absorbed into ordinary life and lose their label.
The trap here is that this tier is the most expensive one. You can spend the most money and buy the second-shortest memory.
Lasts a year, if you get it right
Anything with a date built into it. Tickets to something months away, a booking for a trip, a countdown to a day that has not happened yet. These work because they keep producing anticipation long after the wrapping is gone. The gift is not the ticket; the gift is having something to look forward to.
The risk is admin. A gift that requires him to organise the leave, book the train and remember the reference number is partly a task with a bow on it.
Lasts as long as he keeps it
Things made out of your actual history: the photographs from the year, the places you kept going back to, the songs that got worn out in one particular month, the words you have never quite said out loud. This tier is the cheapest to buy and the most expensive to make, because the cost is attention rather than money.
It is also the only tier that gets better with time. A photograph of a flat you have both since moved out of is worth more in five years than it is today.
What actually decides it
Not the tier. The specificity.
A generic gift from the top tier loses to a specific gift from the bottom one. “A nice watch” is a category; “the pub on the corner where we sat for three hours in February and you finally told me about your dad” is a fact about him that nobody else knows. Nobody remembers the third-best present they were given. They remember being understood.
So before you shop, try this: write down five things that happened this year that only the two of you would recognise. If that list comes easily, buy from the bottom tier and put the effort into the detail. If it does not come at all, that is worth knowing too — and it is a better use of the evening than a shop.
If you go the made-out-of-your-history route
The letter is the part people put off until last and then rush. Do not; there are six rules that make it easier. And choose the places carefully — it is almost never the holiday that turns out to matter.
You can open a complete example to see what the finished thing looks like, or make one.