I have just leaned into being unfashionable and bought a pair of Fitflop trainers, after looking everywhere for comfortable city walking trainers. I expected them to be hideous given the flak they get on here, but actually, they look ok. Minimalist even. And are supremely comfortable. I had trendy Adidas before and they were so hard on my feet. Hate the large, ugly branding on NB, Hoka and other trendy trainers.
I feel the same way about my Seasalt Janelle, now in it's third year, much reviled on here, but I think it looks fine on me and is such good quality. Also my Land's End coat and swimsuit.
What other things do you like that are not trendy, but great quality and you wear all the time?