Below I will attempt to explain what tools I keep in my bag and how I use them. I should start by saying that a more expensive piece of equipment will not give anyone the knowledge and experience required to produce consistently beautiful images. That takes time, patience, and practice.
Canon 35 f/1.4 L
It took me a while to become comfortable with the 35. I learned on a 50, and shot portraits primarily with a 50 for years. 35 always seemed too wide for me. I like the classic feel of a longer focal length. When I started shooting more and more weddings, I realized that a 35 would be ideal for getting ready, large group portraits and dancing. This lens gets a lot of hype and for good reason. It can produce beautiful images.
Canon 35 f/1.4 L vs Sigma 35 f/1.4 ART - I work with a very talented photographer who uses the Sigma in place of the Canon. The images he can produce with it are nothing short of stunning. I chose to go with the Canon version because the Canon Service Center is about 20 miles from my office. Quick turn-around time and no shipping costs for inevitable future repairs and maintnece pushed me towards the Canon. I do not regret my decision.
Canon 50 f/1.2 L
I learned how to use a camera with a 50 as my only lens. When I started shooting portraits, the only prime lens I owned was a 50. The 50 is my go to lens all throughout the wedding day. I use it for details, couple portraits, group portraits, documentary images, and even ring shots when coupled with an extension tube. If I was only allowed to bring one lens to a shoot, the 50 would be it. I have shot entire portrait sessions with a 50 by accident - I would arrive with the 50 on my camera and by the end of the shoot, I would realize I never opened my bag. For me, it doesn't even have to be the 50 f/1.2 L. I had repaired my Canon 50 f/1.4 four times before deciding that the cost of the L version would be worth it if I didn't have to keep replacing the AF system. At the last wedding I shot as a second photographer, the primary photographer dropped his 50 f/1.2 L during portraits. I gave him my 50 f/1.2 L and used the backup Canon 50 f/1.4 the rest of the day. Other than the significant difference in weight and audible focusing, it felt exactly the same as it's larger brother and the images I produced that day were indistinguishable from one lens to the other.
Canon 50 f/1.2 L vs Sigma 50 f/1.4 ART - Again, I work with a very talented photographer who uses the Sigma in place of the Canon. The images he can produce with it are nothing short of stunning. I owned the Canon before the Sigma came out so I really didn't have a choice. If I did I would probably go with the Canon again because, as I've mentioned before, the Canon Service Center is about 20 miles from my office. I honestly can't remember the last time I used f/1.2, however, it is nice to know that I can drop it down to 1.2 if I was in a pinch.
Canon 85 f/1.2 L II
The 85 always seemed to be a little out of reach for me. I could never justify the cost because I really didn't use the 85mm focal length often enough. I owned the Canon 85mm f/1.8 for a few years and eventually I let it go because I used my 50 more often than not. I came across this lens at a price I could not dismiss. Everyone who has shot one talks about how amazing it is, how it's the best portrait lens Canon offers. When I made the decision to buy this lens it felt like I was about to set upon a journey to tame an ethereal beast. It's an odd lens, the manual focus ring is powered by the camera, and it's very touchy. The focal length is neither long nor short for portraits. I shoot this lens primarily at f/2 as with most other primes. I really like how crisp the images look at f/2. I think, for portraits, and the way I shoot, f/1.2 on this lens is usable but I still like the wiggle room of f/2. I use this lens mainly for portraits, ceremony shots, first dances, and toasts.
Canon 85 f/1.2 L II vs Sigma 85 f/1.4 - When you find a Canon 85 f/1.2 L II hardly used, in impeccable condition, knowing who the original owner is, at a price so close to the Sigma it would make you start foaming at the mouth... you don't really think about other options. You just run to the bank and make the transaction as fast as humanly possible. Any questions?
Canon 135 f/2 L
I lack the words to describe the images this lens produces. The 135 is nothing short of spectacular and I would recommend this lens to anyone who wants to take portraits. It's my primary ceremony lens and is amazing for capturing candid moments throughout the wedding day. I shoot this lens at f/2 all day long and the images are simply stunning. It's the only prime lens I shoot at it's widest open aperture on a regular basis. The 35, 50, and 85 all get stopped down 99% of the time.
Canon 135 f/2 L vs Canon 70-200 f/2.8 L (pick a version) - Bottom line is that I chose the 135 because it's light, usable at f/2, and gets the job done. I used to own a Canon 70-200 f/2.8 L and used it primarily for shooting college sports. It was nice to have the zoom range, but when I started shooting more weddings, the weight of the lens just became a nuisance. Someone recommended a 135, I rented one, fell in love, bought one, sold the 70-200 and never looked back. If I start shooting action again, I'll pick up a 70-200 but until then, the 135 gets my pick.
CANON 24-70 F/2.8 L
The 24-70 was my first lens as a Canon shooter. I knew enough about photography at the time of my transition from Nikon to Canon to not buy kit lenses. This lens has been a workhorse in my bag for over a decade. It's still in great condition but could probably use a new hood (not pictured). It's my go to backup lens in case my 35, 50, or 85 bite the dust on a wedding day. It's also handy to have the 24mm focal length just in case an extremely large group shot is desired. I used to own the Canon 17-40 f/4 L, and I never see myself shooting wider than 24mm ever again.
Canon 24-70 f/2.8 L vs Canon 24-105 f/4 L IS - Image stabilization doesn't really do it for me. I have never owned an IS lens. I've shot with them, but never bought one. I owned the 24-70 before the 24-105 came out. I don't believe Canon had an IS lens in this focal range at the time I made the purchase. That being said, if I had to make the decision today it would be tough with all the other options out there. I really don't use f/2.8 when I shoot with this lens so I think a maximum aperture of f/4 would do just fine. I would like to point out a key difference between this lens and some of the other offerings in this category now. This lens is retracted when zoomed to 70mm. It protrudes when pulled back to 24mm which is opposite of what the current version II does. I prefer this type of zoom as that way I can zoom in on a subject and they have no idea. In fact, if they are looking at the camera they may think I'm getting a wider shot when I zoom in and it's a bit more sneaky. I don't think it really matters all that much though. I'm so used to this lens that all the new lenses feel foreign to me. I'm going to be very sad when Canon stops servicing this lens.
CANON 300 F/4 L
You read that title right. There is no "IS" after that "L". I use the 300 mainly for personal work. It's an awesome lens that produces consistently beautiful images. You can see some images taken with this lens here.
CANON Extension tube ef 12 ii
This extension tube is a great alternative to a macro lens. I use this tube paired with the 50 for rings, jewelry, boutonnières, cufflinks and any other small detail shots. I opted for this over the Canon 100 f/2.8 L IS because I didn't want the extra weight. I can only carry so much with me on a wedding day and this little extension tube is tiny, thin, and light. There is no glass in the tube and the images produced when paired with the 50 are amazing.