Judgmentalist
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Thanks for that link - I bookmarked it - I have to be careful with my suits - at 5’8” if I go too old school the proportions shorten me even further - what I like and what looks good on me often don’t get alongAs someone who also wears nice clothes to work (as a musician) and pairs them with hats, may I recommend to you the illustrations I turn to again and again for inspiration and what really brought me back to the Fedora Lounge after discovering them.
https://www.thefedoralounge.com/thr...-mens-fashion-1933-1948-by-flanderian.102763/
You may find them helpful in seeing what various style look like and how they were worn while on your journey to discovering what pleases you. And perhaps, as I do, you'll find inspiration (in terms of what to pair with what) from the clothes as well!
Replying to one of your posts earlier, I'm inclined to agree with your wife that in today's fashion derby/bowler hats seem rather eccentric and perhaps even costume-y. Of course they were standard fare for businessmen through the 1940s and are featured prominently in the illustrations I just shared with you, but they died out even before hats in general did.
Perhaps it is because of my continued interest in those old fashion plates, but I find myself fairly well adhering to the general beliefs about what to wear with what... I don't wear homburgs without a suit, and wouldn't wear a very casual hat like a heathered pork pie with a suit, but find that more casual clothes (both tailored and not) can be worn with a wide variety of fedoras/porkpies/and various straw hats... In short I try to choose a style and shade of hat that compliments what I'm wearing.
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