#1 obviously, and I guess #3 in black.

I think you should get a black leather blazer, for sure, but not that one. Yours should be more like Emmanuel Alt's in the photo you posted: straight cut, thin lapels.

1 and 3- I can't see you in a classic leather blazer like the one here.

I vote 1 and 3. Something about the cut of the lapel doesn't gel with me so much in 2, though I would need to see it in black really to make a final decision.

Agreeing with Greyscale - a less classic blazer would be really fab.

Didn't read everyone's comments but #1 would be a definite. And for my second choice -- I'd lean toward #3 -- but if you want to explore a new area, then I'd choose #2 in black.

Haven't read the other comments thoroughly, but my first impression was #3 in black, then #1. However, the zipper on #3 may be too hard edge for you; although you wear lots of edgy things like asymmetric cuts and the like, they're generally not "hard" like the exposed zipper is, if that makes any sense. So I guess I am on the fence between 1 and 3.

I don't like #2 for you because it seems way too classic and symmetrical, and there isn't much drape. I associate your style with asymmetry and drapey fabrics.

Congratulations on being asked to do this!

I vote #1 and #2! I see this was your order of preference, too. Let us know how they work out!

Yes, the first one would be the obvious choice, but I am not sure that duplicating the same look you favour in clothing in outerwear is the best approach. So I am going to go outside the box here and say that I prefer #3 because it provides just enough drape to mirror your style, but still has enough structure to counter that (which is more important in outerwear, IMO, because it can tend to look heavy anyway), and a lighter colour. And then I would go with #2 because I can really see the red structured jacket popping against a drapey, black wardrobe.

Well #1 seems like a no-brainer! Tell us more!

Another vote for #1 as the obvious choice. Then #3, which I think could work welll with your wardrobe but would be more outside your norm. I don't see #2 as your usual style but I would be interested to see how you styled it!

I'm late to the party (as usual) but since we have very similar tastes, I'm going with #1 and #3 in black. The leather blazer needs some flair to kick it into modern territory, to my eye. I'm not sure about the ties though...to me, they are a tricky proposition and need to be soft/narrow enough to not add bulk, otherwise I've been known to pin or clip to get the shape (in a pinch). I'm psyched for your endeavour too!

Just want to say thank you so much for your input. I have made my decision. Clearly #1 was a no brainer so that is my first choice. I'm going to keep my second choice to myself for now - as a variety of views were expressed re #2 and #3;). What I will say is that both items will be in black. Can't wait to show you and thanks so much for the encouragement.