Like it was said before, it ain't easy trying to measure hydraulics with a tape measure. There are a couple of ways to try to determine size. First look for markings on the hose - for example a 100R16-04 - the 100R16 is the type of hose, the 04 is the size of the hose. I'm sure you've noticed - manufacturers like to put lots of markings on their stuff. Trouble is most of it means nothing to us. So the markings might be different but there should be a telltale "dash size" someplace... IF the markings are not worn off

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Second, look on the fitting itself. Any markings anywhere may help ID the fitting. Look on the nut and on the ferrule. (Note: on two-piece fittings, markings on the ferrule are generally useless) These are usually stamped in. Sometimes they are stamped in well, often the stampings are light and easily covered with grease or grime.
Often the hose and the fitting are the same dash size - such as a 1/2" hose matched with a 1/2" fitting. However it is fairly common to see a fitting markedly larger or smaller than the hose... say a 3/8" fitting on a 1/2" hose or a 5/8" fitting on a 1/2" hose. In most cases you can usually spot this difference by visually inspecting the hose and fitting. This won't help you to actually "size" either one but if you can determine either the hose size or the fitting size it may help you make an educated guess about the other.
Andy