Menswear: Dark dress shirts with dark suits - is it ever OK?

Black suit, red shirt is da bomb.
Likewise, for women: red dress+black hosiery. Having tons of confidence and personal flair helps to carry it off. Not for the timid.

Regardless, the khaki pants+blue shirt look needs to die. NOW.

I like it, but lately I’m a lot more likely to see “shirt, jacket and jeans” than “shirt and suit”. In Spain right now, a guy in a suit has a 99.999% probability to work in sales or personal finance (which is just “sales for people with lots of money”), and I may have left out a few nines.

Wow, a lot of folks work in weird fields.

I’ve worked in very high profile U.S. government and business jobs. The look is common, and can easily be executed well. I personally wear plenty of royal blue shirts with dark suits, it’s a good look. Dark purple will work as well, but that’s admittedly a more bold choice.

That said, you won’t see black shirts. That’s a casual look, or an “alternative business” look, i.e. you’re not going to find a lawyer/banker/broker wearing that. Done wrong, yes, it’ll look like the stereotypical mobster look.

As far as the rules are concerned, the rules are meant to be broken, with confidence. That said, as a general rule, you don’t wear a shirt darker than the suit you are wearing, and you don’t wear a tie lighter than the shirt. However, I routinely pair ties with the same color shirt-- that’s a simple bold look, nothing unprofessional about it.

Chuck Bass has fantastic fashion sense. It’s definitely not conservative, though.

Those would be white and light yellowish-green, amiright?

The look can be done, but it shouldn’t be done regularly.