You can directly install software for Debian from .deb package files, but using the APT package manager (or a front-end such as Aptitude or Synaptic) to get software from the official Debian repos is much safer and cleaner. Here are instructions and hints for installing your preferred version of Wine, the Debian way....
For 32-Bit Debian
So long as your package system is configured correctly and up-to-date, grabbing Wine should be simple, whether you use Debian stable, testing, or unstable. On 32-bit Debian, you can install a stable release of Wine with a single apt-get command:
sudo apt-get install wine
Starting with Debian Jessie (release 8.0), there is also a package of Wine's development release that can be installed alongside the stable release:
sudo apt-get install wine-development
Note that you currently need to use the command 'wine-development' instead of 'wine' to run the development version from the command-line.
You should be able to closely track upstream with the "wine-development" package. While the version on stable will only upgrade with each major Debian release, current packages for users on stable will be regularly available from Debian Backports (see below for details). Similarly, the packages in testing and unstable won't be updated while Debian is in its biennial code-freeze. Advanced users that really need a packaged, cutting-edge version of Wine during those months can still find it in Debian experimental.
On 64-Bit Debian
Even if your system uses 64-bit Debian, you probably still want a Wine installation that can run 32-bit Windows applications. To install 32-bit application support, just make sure your system is configured to pull in 32-bit packages and the index is updated first:
sudo dpkg --add-architecture i386 sudo apt-get update sudo apt-get install wine-development
Starting with Debian Stretch, you can also install Wine on 64-bit ARM systems:
sudo dpkg --add-architecture armhf sudo apt-get update sudo apt-get install wine-development
If you are on stable and want a newer version of "wine-development", starting with Debian Jessie, you can grab a version in sync with upstream from Debian Backports. To install it, you need to enable the Backports repo first by adding the following line to one of your sources.list files:
deb http://httpredir.debian.org/debian/ jessie-backports main
You can do this either through Synaptic (Settings -> Repositories -> Other Software -> Add) or by editing the sources.list file directly ('sudo editor /etc/apt/sources.list'). Then once you've added your sources, update your package index (Reload in Synaptic or 'sudo apt-get update' on the command-line).
If you don't mind possibly upgrading other dependencies to Backports versions too, you can install everything from the command-line in one swoop:
sudo apt-get install -t jessie-backports wine-development
If you want to be more selective about keeping stable dependencies though, you can use the form:
sudo apt-get install wine-development/jessie-backports
However, if any other packages need to be installed or updated, this method will abort with a list of such packages. You can selectively install those from either stable or Backports, then repeat the command to install "wine-development/jessie-backports".
For more info, you can see the Debian package site:
There are also useful wiki pages out there too: