Wearing Clothes That Are Out Of Style

Totally agree.

However, one has to be careful with the term "conservative" and "strange" clothes nowadays as, very curiously, what one would consider "conservative" and "conformist" in a XX century view-point, stands out today as "strange" and "unusual".

For example, in my hometown (a small village in the hills above Firenze, in Italy) it would source of great attention just to walk around in suit and tie during any weekday, while this would have passed totally unnoticed until, say, 20/25 years ago. And yet what's more conservative than suit and tie??

 

I have noticed a lot of 'Out of date' clothing being worn these days with modern fashion, Peaky Blinders caps with Harris Tweed trousers, jackets and waistcoats or skinny jeans, brogue boots etc, it works well. You don't have to be Steam Punk but some of that can have a good mix and match with modern also.
As said previously if worn with confidence most people only notice the items they like and forget about the rest. I doubt a full on Bertie Wooster look would go down well at your golf club but loose the plus fours and maybe? leather jackets can also fit in, not so much the genuine 70 or 80 year old vintage garments that actually look 70-80 years old but good quality reproductions would be ok.
Back in the 1960s old military uniforms were the thing with the Carnaby Street lot so it looks like it is not just a recent thing.
Me? I will only wear a bike jacket of any era when on a bike, I feel like a poser if I wore one without a bike but thats just me. Hawaiian shirts, I just bought some replica's to wear on holiday simply because I like to be seen in something unusual that is unlikely anyone else will be wearing strolling through holiday villages etc.
Keep it up chaps and chasess's and wear what you like. Jay Tee

 

What choice do you have when the current styles and materials are so awful? I'm convinced that the current Pee Wee Herman style of suiting will look as silly as 1970's Disco styles twenty years from now. Most of what I see these days is exercise clothing, which is one step up from pajamas.