>
>Any style of clothes can be comfortable, properly fitted and cut.

Those trousers with the crotch somewhere knee high probably cannot be fitted properly...
But mostly you are right: you have to know your size and what brand fits your figure this decade...
And spending enough money to have quality material helps also a lot

>
>Sometimes, even with a client, you may want to send the message that you are different.

Here I'd say you should always point out that you are different - but not neccessarily on neandertal or woodstock level.

> in the 90s if you were 20 and said to be a computer whiz the suits expected youth and t shirts. If I'm 20 years older than my clients and want to convey wisdom, play up the grey beard, and justify the Big Hourly Rate I may want to do a cashmere jacket even if they are business casual.

Yupp, early 80's I had a Zegna and very expensive sneakers to CEBIT. Most of the people told me they wished they had the guts to do likewise, as the feet were even more put to work than the brain during the day.

When in working in insurance inhouse 10 to 15 days per month I usually went in
with expensive suit, second pressed shirt and an unbound tie
for such times as it was ***really*** necessary, which usually was once or twice with each stuffed shirt
- everybody was quick to point out that THEY were not in THAT category.

Probably some of them only to make that odd duck feel at home,
because if they need some brilliant idea or something budgeted for a month in 3 days -
which was exactly the niche I was aiming for - interesting work, even if more taxing,
but also time to goof off on sub projects with ROI only clear to me, not managment.
Pulling those partially working separate tasks out of the hat
when something big hits the fan was the icing...

The big question is when to stop at being different is the best compromise between income and personal preference.

>I figure it's a costume. Cover. Legend.

So putting some thought to it is better than to just throw money at it -
similar to purloined letter reasoning...

my 200$ (for an italian shirt)

thomas