Suit & tie, Top hat, Cape, Cane
Also, what might you have him add/remove before dating him?
Most Helpful Girl
Definitely not a top hat, cane/cape. It's not old fashion, it seems more outdated so it would come of as weird. Of course if you were dressing up for a costume party, etc. it'd be a great outfit.
Stick with slacks and a shirt - it's kinda formal, but if it looks good on you, work it! To make your outfit more casual, unbutton the top 2 buttons and roll up your sleeves, you could also switch out of your work/formal shoes into loafers like:
You can't go wrong with a pair of Chino pants, becasue you can dress up or down with them. It's a must have for your closet. Here's an example:
^ the guy looks super hot and stylish. His outfit is effortless yet draws attention :)
Most Helpful Guy
A top hat isn't worn with a business suit, nor is a cape.
A top hat, cape and cane would be work with evening dress, in theory, if one had somewhere formal enough to call for it. Note that evening dress is worn in the evening.
If you are going somewhere exceptionally formal in the daytime, you'd wear a morning suit, even if its in the afternoon. A top hat would be worn with that, were one outside. If you manage to swing yourself an invitation to the royal enclosure at ascot, for example, such dress is -required-.
Your cape and top hat in the evening would probably look odd even with a tuxedo. With white tie, it would be appropriate.
I'm hoping you recognize that the hat, cape and cane are outerwear, and come off when you go inside.
Slapping these things together when not called for, or with the wrong things, or even wearing a suit where a suit isn't appropriate, is wearing a costume, not dressing in a formal way. You can express yourself however you want, but if you're playing costume, you can't be surprised when people -view- it as dressing in a costume.