avoid fashion and stick to style, you get more value/wear out of your clothes that way.
I just stick to what I like, and spend enough on it to make sure it lasts a long time, plus I have enough different items to not wear stuff out quickly. I was wearing a long-sleeved tee shirt I bought at a gig in 1989, it still fits just fine. Same goes for jeans, shirts, jackets, etc.
Finding regular-fit jeans on the high street was something of a challenge.
That’s where you’re going wrong, the average high street doesn’t sell jeans of a decent quality or variety, about the only places I know that do a reasonably wide range are skate/surf shops, and Uniqlo, and they only have outlets in London. I did try some of their selvedge Japanese denim jeans on when in London, which was good, because they size small in the waist, I’m a 32, but a 34 fitted perfectly. Leg length was spot on, though.
Their regular relaxed fit are just like classic 501’s, without any fancy stitching, and I recommend them highly, plus they’re very competitively priced.
That photo above of Angry Tinkerbell at a podium made me laugh, he can’t even wear a flying jacket without looking a tit! I’m not even sure it’s a genuine military issue jacket, either.