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Middle-aged man, I want update image/clothing, where do I start?.

Wow, I do really like that and that's rare. But they seem to have put their decimal point in the wrong place.

Wouldn't you rather have one set of clothes that you really liked than 5 that were meh?
 
Someone I know buys all sorts of cheap clothing and usually within a week or so of having them he has died them all black.
 
Wouldn't you rather have one set of clothes that you really liked than 5 that were meh?
Yes, but I have a tendency to clumsily catch my clothing on things or stain them or otherwise cause disaster. If I did that to a £350 shirt, I'd be a bit peeved!
 
Just remembered these people. A bit überhip maybe, but I really like the way they sell clothes:
Old Town - British clothing designer and maker

(you choose the style and the fabric, they sew it for you, like proper tailors.)
That looks nice. Also, they are clearly equal-opportunity employers, even going so far as to employ a model whose head is tragically upside-down:

Capture.PNG
 
Are you up for critiques from anonymous strangers on the internet Winot? If not please ignore me but if yes, I'd swap the colours round, the white bottoms with rust on top looks a bit top heavy.

Yeah it's quite a difficult jacket to pair. Works OK with jeans.
 
Well... factory aged & distressed clothes have been a thing for years for a reason.

None of the workwear scene guys keep their clothes pristine - part of the point of wearing clothes like that is that they age well, they look good patched and sewn. Some 'Bros will talk about how an item of clothing 'tells a story', but tbh I reckon that's imbuing too much meaning into it.
 
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