I’ve always been a fan of more traditional looking clothes, but I am ware that if I wear things that are to my personal taste I will risk looking affected and like an old man.

I’ve always loved felt hats and vintage suits and ties for example, but we all know that’s the sort of thing that can look painfully out of place in the 21st century, especially on someone of my age (18).

How would you recommend finding a reasonable middle ground between old fashioned, dated clothing, and modern street wear/overly casual clothing that just doesn’t appeal to me. I often like wearing buttoned shirts tucked into pants, but I feel like this will look out of place in a college environment.

(Also I don’t know how relevant this is, but I am a chubbier guy, around 250lbs and 6’1”, and I often feel uncomfortable wearing things like short sleeve t shirts and shorts because I feel they are often unflattering on my body type)

TL;DR: I would appreciate some advice on more classic/old fashioned looking clothing that will not make me stand out like a sore thumb among my peers.

Edit: I really appreciate all the helpful responses I’ve gotten. I was a bit reluctant to post this but I suppose most of the people who get shit on here do so because they are adamant that there’s no such thing as looking dated while dressing straight out of the 1940s