Just Say NO to "Dressing Down"
"rather formal" -- EXCELLENT
"almost military" -- WONDERFUL
"can look ridiculous" -- ESPECIALLY WITH JEANS
I confess to a nasty anti-denim prejudice and I do thank the Gods that this remains the only fashion offense that still manages to get someone kicked out of the Yale Club. Besides being ugly, denim is too hot for warm weather and certainly doesn't help much in cold weather -- mocked even in OPH long ago. An even greater sin is that it is SO COMMON -- American Middle-Class Conformity at its worst. There are other working-class fabrics adopted by the gentry that look better and work better: corduroy, moleskin, flannel. And then from the military we have gabardine, whipcord, cotton khaki...
And would it kill you to wear a tie once in a while?
"Square" does not equal bad and "Formal" can actually be a better choice than "Casual" -- particularly as these terms are thrown around today.
One more thing: Shoot for the Stars! Be better-dressed than 99.8% of the ***** out there and if Thurston Howell is not your type, try Fred Astaire, Cary Grant, The Duke of Windsor, and countless others from the not-so-distant past.