For once I really don't know what lens to get - it's all Ls !

At the moment I actually have all the lenses that I need. But I am looking for something that I could experiment with now. Most of my work is wedding related, some portraits.

Currently I have

16-35/2.8L mk1
24-70/2.8L mk1
70-200/2.8 (Sigma) Seldom use

35/1.4L
50/1.4 (Canon)
85/1.2L
85/1.8
135/2.0L

Price isn't really a concern, up to £1,500/$2,000. I have made a shortlist and here they are

24/1.4 - Something wide for weddings evening shots on the dance floor.
50/1.2 - just so I can upgrade the 1.4 to this (not sure if it is worth it)
100/2.8L IS Macro - useful perhaps for detail shots

A Tilt/Shift lens, not sure which one, i would think the 45mm T/S would be best as I love the 35mm on my 5D. I have seen some amazing T/S portraits and would like to try that for myself.

Ideally I would get them all but i can't afford that !

100L IS Macro, interesting, versatile lens and very reliable in getting the shot. Some use it for wedding rings, gifts, decorations, personal and remembrance details.

I take mine out for a spin often just because it's fun to use, IQ and SHARP.

If I were picking a purely fun lens, it would have to be either the 8-16L or TS 24 MkII, myself. Either one of those would be fun to muck around with when specific shooting wasn't in order...

The 100 macro is also a fun lens, but I already have that, so didn't put it into the "figurative" category

yep, reported

Snydremark wrote in post #13939270
yep, reported

...twice

My pick will be the 50L and the 100L macro! Your 16-35 already covers your wide side, the other two will be more practical IMO.

If you seldom use the 70-200 Sigma I would think about a 24-105. You would be able to get in closer than with the 24-70 and it gives great results. Don't worry about the F/4 vs. F/2.8....with IS the 24-105 will get it done and gives a great look. Every portrait, wedding, event photographer should have one. Just a thought.

On you list.

100mm Macro. You can get great detail, portrait, and ring shots......and a lot more. I have been surprised how much use my 100mm has been getting. Mine isn't even an "L" version and I still love it.

Do you find the 16-35mk1 and 24-70mk1 good enough?

Theres a great opportunity to upgrade both of those now. Or even change the sigma 70-200 for a canon lens, 85f1.8 or 135L?

"24/1.4 - Something wide for weddings evening shots on the dance floor."
Good low light lens, nice idea, usefull for weddings, need it as well as the 35L tho?

"50/1.2 - just so I can upgrade the 1.4 to this (not sure if it is worth it)"
Nope, not worth it IMO.

"100/2.8L IS Macro - useful perhaps for detail shots"
Good idea, great lens, and possibly ditch the 70-200 for it?

"A Tilt/Shift lens, not sure which one, i would think the 45mm T/S would be best as I love the 35mm on my 5D. I have seen some amazing T/S portraits and would like to try that for myself."

TS portraiture is great but it will take time and effort to set up, not very dynamic at all.

Entry macro - canon 100mm 2.8 usm + kenko extension tubes + reverse ring ( additional 50mm 1.4 w/ reverse ring and 67/52 coupler)

Tilt-shift - 17mm for extrem creative pics
- 24mm landscapes/buildings(m​k2)
- 45mm protraits/product
- 90mm macro/close-ups
...just as examples

The first two ts-e might burst your budget if brand new

Macro 100mm would be a good lens to play around with, good for those close up shots at weddings.

If you are just looking to experiment, and offer something different, have you though about getting an IR adapted body?

You could do some fun stuff with that.

I would go for a fish eye lens

I use my 100L macro for so much other than the obvious macro shots. It's a great portrait lens, specially on a 5D2. I'd also agree with Nate42nd, a 24-105 f4 L is also great for portraits and f4 hasn't been a problem yet with mine. I use it about as much on my 7D as I do with my 5D2, even though it was the kit lens with my 5D2. The IQ is excellent on both of the above lenses and I'd never hesitate to recommend them.

Canon 70-200 2.8 IS II

I'm not really a big fan of fisheye, both in its resulting effect and it's application. Nor my style require the canon 70-200 mkii. I've not used the sigma in over 18 months because that's not the focal length that I shoot with.

I'm really tempted by the 100mm macro, mainly for the macro side of things but less so for it as a portrait lens. I have the 85L and 135L for that. So I'm unconvinced what the 100mm will bring to the party. I am intrigue by what I can do with its macro features though.

Same as the 45 TS, only concern is that it is a very old design and fear it'll get replaced soon. Seeing the 17 & 24 TS got a refresh last year.

However, you guys have given me food or thought, IR could be a possibly, and I guess the 8-15mm could be too, need to see more samples from it first, it is still a very new lens.