I remember it didn't really bother me much when the show was new. It was noticeable of course, but it just seemed that Picard had offered leeway on his bridge, Wesley's stupid gray 'acting' ensign jumpsuit, Beverly ambling about in an ugly green lab coat, Worf wrapped in a tank tread, & Picard himself experimenting with different fashions, the most laughable of which was his puffy vinyl shoulder pads
Lest we forget, Troi spent most of season one in a gray jumpsuit & an updo. It was far less casual looking than the maroon & lavender suits, but ugly as hell. Heck sometimes you'd see her on the bridge in the teal dress with the oblong neckline
That's why it always struck me as pure hypocrisy for Riker to reprimand Ro for wearing an earring like a stodgy douchebag
I remember watching that scene & thinking "Dress code? On that ship? Are you shitting me?"
It does annoy me a bit in hindsight, but that has more to do with the fact that it became a meme with every Trek show to follow, that the bridge crew had to have someone without a standard Starfleet uniform. That's when it really became ridiculous