DorianGreen
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I think that, after much ado about Crompton's integrity or supposed lack thereof, we're back to the classical forum standoff of "anything I don't routinely personally see worn in my social circle or at least environment, is outdated and customey, it would look ridiculous if I wore what X guy wears" vs "Y guy is cool because he wears whatever he wants with pride" vs "Z guy is safe but boring".
I don't really have a groundbreaking solution either. I tend to lean more in the second camp simply because I think most people grossly overestimate how much people care about your choice of clothing and underestimate how much the "stand out" problem is mostly your own perception making you uncomfortable (within reason, ofc bright yellow suits are not accounted for here). For example, I don't think anyone would be dumbfounded by anyone wearing cuffed, pleated high rise trousers - I wear mid-to-high trousers, often pleated and cuffed, nearly everyday, people (largely in imho atrocious low rise) don't even realise, even though i know literally ZERO males that wear them beside me. I do not wear suspenders though, and my trousers are RTW, so the highest rise trousers I have don't really stay truly as high as they could anyway.
For the record, I'm early 30s, and get a lot of compliments for dressing in mostly casual tailoring at work. Outside of work, it's more often shirts and casual refined jackets, but on occasion soft tailoring as well.
I do know some select few people who love making fun of me and saying I dress "very old"... but it's also people who I believe have 0 sense of style yet think they're "cool" because they wear black or something, so...
That being said, I'm sure you can in fact go too far. I'm not talking about ties, which may not be worn much but are still very much in everyone's mind, but more like bowler hats, morning dress etc etc.
Well said. If you are authentic and wear what you really like and is expression of yourself, you never feel overdressed or uncomfortable, and you'll be mostly complimented for your style.
But it's right, we tend to overrate others' percection of ourselves: the most people won't care at all. And certainly it's preferable to stand out for dressing carefully rather than sloppily.