1. See your files by date
Before moving anything, get File Explorer to show the dates:
- 1Open the folder and choose View → Details.
- 2Click the Date modified column heading to sort newest or oldest first.
- 3For month-by-month groups, choose Sort → Group by → Date modified. Windows splits the list into Today, Last week, Earlier this year and older months.
2. Move them into year and month folders
Create a folder per year, with a folder per month inside it (2026\01, 2026\02…). With the list grouped by date, select a whole group by clicking its first file, Shift-clicking its last, and dragging it into the right folder. It's slow for big folders, but you only have to do the backlog once.
3. Keep new files sorted
The backlog is the easy part: the problem is the 20 new files that land next week. Windows has no setting that files them by date as they arrive. A TidyFile rule does: it watches a folder such as Downloads, files each document into its year and month folder, and creates the folders when a new month starts. If it's photos you're sorting, see sorting photos by date.
The TidyFile rule
Documents by month
- When a file
- in Downloads · type is pdf, docx, xlsx, pptx
- Then
- move to Documents\{year}\{month}
Set it up once and TidyFile applies it in the background, to new files the moment they arrive. Preview what it'll do to the files already there, and undo anything from the activity log.
Questions
Which date should I sort by: created, modified or date taken?+
For most files, Date modified is the most reliable: it's set on every file and survives copying. Date created resets when a file is copied to a new drive, and Date taken only exists on photos.
Can Windows move files into date folders by itself?+
No. File Explorer can sort and group files by date, but it never moves them. To file them into year and month folders you either drag them yourself, run a script, or use a tool like TidyFile.
What folder structure works best?+
Year, then month as a number: 2026\01, 2026\02 and so on. Numbers sort in the right order, which month names don't (April would come before January).