Style Advice Please: Does Dark on Dark Work?

Only if you want to look like a gangster.

I was gonna say what r1 said, essentially: "Yeah, if your last name is Moltisanti."

I think it’s a sexy look but probably not best for everyday professional wear. It’s also definitely a funeral look.

I can't decide, but this made me chuckle -

Dark greys would offset the mob look

IIRC, it was fashionable for about 20 seconds in the early 00s-- a tie in the same color as the suit.

But in 2020, you will look like a hitman.

Or Matt Gaetz

Well a double breasted coat is a bit overdoing it now. At least it wasn't a bright red shirt under a black suit.

Very 90's to me.

R5 so something like this?

I think it would be very difficult to get the tie, shirt, and jacket to be the exact same shade of black. If they aren't it would look cheap.

The George Raft look is so 1935, OP

try a turtleneck

I think it’s perfect for the age we’re in. Times are dark.

Some blokes definitely pull it off, still look interesting, but I would feel as if I were trying to channel Johnny Cash.

I think a dark suit + dark shirt combo can work, but it usually needs a splash of color in the tie and maybe a pocket handkerchief. I also wouldn't advise it for fair-skinned blonds.

What about olive skin tone complected latinos?

Let’s stipulate that you have to be good looking. That is the part everyone forgets with big fashion moves.

OP's photo is gorgeous. The midnight blue expertly tailored suit and dark shirt and tie are perfect.

The monochromatic theme was popular in the very late 90’s early 2000’s.