In 2021 I bought 12 different types of printing blanks (iirc it cost $150 for everything) of various fits, gsm and fabrics to test my preferences and then stuck with the tshirt I preferred the most. Donated/worn out the rest, and only purchased the one I liked moving forward. I've been lucky with other purchases but those were also guided by gear recommendations from niche subreddits and picking whatever was on discount among them. And because I buy them on a discount, it's usually not THAT big of a hit to the pockets after reselling them if I don't like them for whatever reason (other than durability which there's no getting around to. seams, stitching, materials etc are a good tell, however).
There's always some randomness, for example I once had to rush to H&M for an emergency blazer when I showed up to an university event in a tshirt and the Queen of Denmark arrived. I got a bit drunk that evening but I remember I walked home in the evening without it.