It is, or should be, a bit of fun and a subculture to get involved with but it's not day to day style. I've never read The Chap but I did for a period have a big handlebar 'tache and dressed up in suits and hats, mainly to go out to burlesque clubs and the like. It was a laugh but it was costume really, not style.
Dragging the thread back towards the OP and actually being boringly serious for a moment, I would make a point that I've made before. Clothing is cheap. Far too cheap. If you've got enough clothes to be getting on with then don't change your entire wardrobe all at once. And don't buy cheap shitty sweatshop made clothing. Instead buy a couple of things at a time, that way you can afford better, more ethically made and sustainable pieces. That way when you put them on they'll feel special, you'll feel better and you'll hold yourself better and carry yourself differently and look good for it. Then figure out how to make those nice clothes work with what you already wear, and what else you might want to buy to complement them. Think about where and how often you're going to wear things. Sure, a three piece tweed suit is a nice thing but where will it get worn? I got married in mine and I've worn it to other weddings but that's about it.
Take it slowly and work it out yourself, dress how you like and how you feel comfortable, don't go changing everything just because some bald twat standing in a field tells you to.
Or don't. It's only clothes.
Thanks - that pretty much summarises the way I was seeing things too
For now daily wear's sorted with many combats and plain T-shirts - I must admit I'm a sucker for Primark slim-fit T-shirts as they fit well / look good and are dirt cheap. Totally appreciate your point about ethics though and having owned some examples for a while the lack of quality is starting to become apparant through baggy / failing elastic at the collars.. so in future I'll look to move towards a lesser number of higher-quality T-shirts or more presentable alternative such as Henley or Polo shirts.
I try to wring the most use out of anything I have, so in the case of clothing stuff that becomes too tatty for daily wear gets relegated to a "work" pile, then finally consigned to the rag bin which sees them used for household cleaning / jobs on the car, bike etc.
I have some more design-centric T-shirts and a few smart / casual shirts, along with a couple of pairs of light tan charity shop chinos that I'm as yet undecided on.. some decent jumpers and a couple of nice skinny merino wool offerings. It's the smart/casual and formal stuff I'm a bit lost on as I can appreciate the look from a purely aesthetic perspective (let's face it, everyone looks great in a nice, well-fitting suit / suit jacket) however (other than on properly special occasions where such dress is mandatory) none of it really feels authentically me.
I hear you on the suits, although tbh as long as the cost is manageable I'm happy to indulge myself a little as tbh I'm sick of being the guy who's been seen in the same generic off-the-shelf suit at every event for the past 20 years; having blindly, begrudgingly panic-bought it out of necessity. Tbh the last suits I bought cost me less than a ton for the pair (plus maybe a bit on top for some minor tailoring) - so a little treat that won't break the bank and should hopefully last me a long time.
I'm hoping that the vintage angle should tick a lot of boxes - much lower cost, better quality and the availability of stuff that I like / remains stylish but is currently out of fashion so rarely available new.. plus maybe a bit more financial comeback should I want to part with any in future. I'm trying to keep the reins tight as I'm still learning what's what and ideally want to lose a bit of weight again if possible.. however I'll allow myself a decent long wool overcoat if something decent comes up at a reasonable price. I've done a lot of homework into sizing so feel more confident ordering blind online, and have my eye on a nice looking used H&M coat that looks like a good fit by the numbers.. it won't be the best quality in the world but worst case should do as a stop-gap and a cheap way of assessing what sizes actually fit me as the only frame of reference I currently have are suit jackets and some of my old chap's massively oversized coats.
On from that I'm looking at a couple of pairs of presentable dark trousers (chinos or jeans), maybe a nice roll-neck jumper (your contribution duly noted
@Accy cyclist!), maybe some footware to bridge the gap between my tatty old Scarpa climbing shoes (which will be replaced like-for-like as they're great) and the posh shiny brogues I bought recently.. I also need to sort out some proper cycling clothing; although that's its own rabbithole to be ventured down at a later date..
Ultimately yes, I plan to just plod along, keep learning, keep watching
ebay, keep bothering the charity shops and see what turns up