Originally Posted by ktrp
A question that cannot be answered, I fear. Several decades ago, stylish men from warmer climates decided to stop wearing hats entirely when dressed well. Stocking caps look about as good with a suit and overcoat as running shoes do. Unfortunately, most young men stopped wearing any other sort of winter hat. If you can look good in a fedora or similar, more power to you. I feel I would look 'costumey' wearing one with a suit. I actually think its easier to pair a traditional men's hat with streetwear and not look costumey then with a suit. Suit + fedora + overcoat = full anachronistic dress. I'm considering going for a flat cap, as suggested above, though I haven't pulled the trigger yet. I'll probably start with a cheap one and see how I find it. If you decide to look into a nicer one, I saw someone with one made by Hanna Hats of ireland that looked terrific. They are available through that companies website in a variety of tweeds, and in both a traditional and a 'more fitted' look. My father always wore a black Karakul hat, the sort one now sees most on central asian politicians, though I would say he wore it a little lower then they do. To me that still draws less attention then a traditional brimmed hat when paired with an overcoat in winter.
You have it a bit backwards there - when an overcoat is worn, a proper hat doesn't look costume at all, because then it serves an obvious utilitarian need (cold weather). When worn only with a suit. a hat is a problem for some men, but usually they just choose the wrong hat. If you buy that flatcap I hope you choose carefully - colourful tweed caps will look horrible with a city overcoat, especially at night time. One option might be a solid dark gray ascot cap... in any event, coordinate the cap and coat.
Several decades ago, stylish men from warmer climates decided to stop wearing hats entirely when dressed well.
And which decade was that, specifically? It couldn't have been the '60s -
- or the '70s -
or even the '80s:
I suppose you must have meant the '90s. That's alright then, there wasn't much style in the '90s anyway.