The moment it clicked for me was standing at the kitchen counter on a Sunday morning with a pitcher of orange juice catching the light, and realizing it made the whole table look like someone had thought about breakfast instead of just surviving it. Same juice, same glasses, but suddenly the table felt like a place you wanted to sit down at rather than a place you grabbed a bowl and left.
Sizing one of these right comes down to thinking about what it's actually for before you think about how it looks. A big half gallon pitcher is wonderful for lemonade on a hot afternoon or iced tea on the porch, but it's a nightmare to lift one handed when it's full, and it hogs the whole fridge door. Something in the one to one and a half quart range handles water at dinner, juice at breakfast, and a cocktail for two without needing both hands or its own shelf. The mistake I made early on was buying one that looked perfect empty on the counter and turned out to have a spout that dribbled down the side every single time, so pick one up in store if you can, or at least read what other people say about the pour, because a pitcher that leaks on the tablecloth stops getting used within a week.
Where a pitcher really settles into a room is next to the everyday glasses, not shut away for best. It sits well on an open shelf with a stack of plain tumblers, or on a kitchen windowsill where the morning light comes through it, which honestly is half the reason I like glass ones over anything opaque. In the evening, with a lamp on rather than the overhead light, even tap water in a pitcher on the table makes dinner feel a little more deliberate, a little less like everyone's just refueling. It doesn't need a matching set of anything else to make sense, it just needs a spot where you'll actually reach for it instead of the jug from the fridge.
If you own none of these and want to start with one, go for a plain glass pitcher with a simple handle and no cut patterns to scrub out, since that's the one that moves between orange juice in the morning and wine at dinner without feeling wrong either way. Measure your fridge door shelf and your cabinet shelf height before you buy, because a pitcher that is an inch too tall to stand upright is one you will end up leaving out on the counter forever, whether you wanted it there or not.