Term to describe the purchasing of an expensive item, of excellent quality. Implies that the owner will, initially, have reservations or guilt for buying such an expensive item; however, the owner soon realizes they will only have to purchase the item once. Owing to its craftsmanship and durability, the item will have a long lifespan.
Bob: "Dude, this iPhone case cost me $200! It's made from Italian leather and handcrafted in Eastern Europe, though..."

Frank: "Ouch... Buy once cry once, amiright?
by Robert McCall September 26, 2015
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To begrudgingly spend money on an item of higher quality or containing more features to prevent yourself from having to buy something else in the future to enhance or replace your original purchase.
"I could buy this cheap gaming computer, or spend a bit more money to buy the one that is more future-proof. Buy once cry once! "
by CaptainKnotts February 2, 2023
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