Try this:
var subject = "category/all-weather-wicker/bermuda/item/bermuda-end-table/table/2977/";
if (/^category(?!.*?\/item\/\d+\/).*?$/im.test(subject)) {
console.log("passed");
} else {
console.log("failed");
}
LIVE DEMO
EXPLANATION:
Assert position at the beginning of a line (at beginning of the string or after a line break character) (line feed, line feed, line separator, paragraph separator) «^»
Match the character string “category” literally (case insensitive) «category»
Assert that it is impossible to match the regex below starting at this position (negative lookahead) «(?!.*?/item/\d+/)»
Match any single character that is NOT a line break character (line feed, carriage return, line separator, paragraph separator) «.*?»
Between zero and unlimited times, as few times as possible, expanding as needed (lazy) «*?»
Match the character string “/item/” literally (case insensitive) «/item/»
Match a single character that is a “digit” (ASCII 0–9 only) «\d+»
Between one and unlimited times, as many times as possible, giving back as needed (greedy) «+»
Match the character “/” literally «/»
Match any single character that is NOT a line break character (line feed, carriage return, line separator, paragraph separator) «.*?»
Between zero and unlimited times, as few times as possible, expanding as needed (lazy) «*?»
Assert position at the end of a line (at the end of the string or before a line break character) (line feed, line feed, line separator, paragraph separator) «$»