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Yeah, I’ve got plenty over shirts and a few pairs of selvedge, and a set of redwings etc. but heavy wool, stiff denim and leather boots just feels a bit fucking boring.
Also, it’s fucking annoying when all my over shirts and stuff come down to my thighs because I need to size up to fit my chest. Which then looks stupid as fuck when it’s under a jacket that’s cut to your waist.
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Sounds like vintage fit knitted jumpers will work well, tend to be a boxier fit. Check North Sea Clothing https://northseastore.myshopify.com/, esp this https://northseastore.myshopify.com/collections/wool-knitwear/products/copy-of-the-mariner-navy-blue
I echo what other says. Invest in the basics, find some brands you like and set up searches in ebay. I haven't bought anything new in years, if not a decade
Regarding the classic menswear stuff as in selvedge denim/wolverine shoes/lumberjack shirt and all that stuff, it can be great, or you can end up looking like a wannabe Canadian tree felling guy.