Which Lens Should You Buy Next?

So You Want to Buy a New Lens?
Buying a new lens is a big decision. The lens you choose can have a large impact on the quality of your images and on your shooting capabilities. There are a lot of different lenses out there, and many are amazing for totally different reasons. I think it's important to have a variety of lenses that can achieve a variety of things, but lenses are expensive, so it's best to understand your needs in a lens to be sure you're purchasing the best ones for you.

I get asked a lot about which lens is my favorite. And it's tough to answer because my "favorite" changes all the time. It depends a lot on what I'm shooting and what my intention is. Occasionally, I will shoot a whole session with just one lens. But majority of the time, I am changing my lens multiple times during the course of a session. Having the subject stay exactly where they are, and taking the same exact shot using two very different lenses can completely change the whole look of the shot.

Which Lenses Do I Recommend?
I can really only speak about the lenses I own and shoot with, because those are what I know and what I'm comfortable with. The lenses I have and am able to recommend are the 28 1.8, 50 1.4, 50 2.5, 85 1.8, 24-105 IS 4L, 70-200 IS 2.8L II, 24-70 2.8L II. All of these lenses are Canon. The first thing about lenses that is important to understand is that lenses fall into two categories- fixed/prime lenses and zoom lenses. Prime lenses have only one fixed focal length and cannot be zoomed in or out. Zoom lenses, like the name suggests, can be zoomed in or out to different focal lengths. There are pros and cons to both types of lenses. I separate my lenses into these two categories below.

Fixed/Prime Lenses: One fixed focal length. Cannot be zoomed in or out.

28mm 1.8:
I love this lens for wide-angle shooting. Wide-angle shooting is great when you're wanting to capture a lot of the landscape/environment surrounding your subject. It adds some great depth and dimension to the image, and is great for telling a story that involves the surrounding.
The barreling effect it can sometimes give to the subject makes it not a fabulous portrait lens, but Lightroom has some great corrective tools to fix this.
Another great thing about this lens is that because it is so wide, and it lets in so much of the surroundings, it allows so much of the surrounding light to help brighten the image. That, plus the fact that the aperture can go as wide as 1.8, makes it an excellent lens for indoor shooting, especially for events when you want to capture a lot of scenery in a small space, such as a table spread, a dance floor, etc.
Find more info on this lens at Amazon.com by clicking here.

50mm 1.4:
This lens seems to capture the closest to what we actually see with our eyes when viewing an image. It's more of a "real-life" lens, and is perfect for day-to-day shooting. The 1.4 aperture is great, and the versatility of this lens is great. This is always the prime lens I recommend someone get as their first lens once they've bought their first dslr.
Find more info on this lens at Amazon.com by clicking here.

Macro 50mm 2.5:
This lens is very similar to the previous lens, but this lens has macro capability, which enables me to get very close to my subject to get detail shots, such as a wedding ring's diamond or a newborn baby's toenails. I don't use it too often, as I really only use it for these purposes.
Find more info on this lens at Amazon.com by clicking here.

85mm 1.8
This lens is amazing for portraits. It makes everything pretty close-up in your camera, which is great for focusing on faces. Because of this compression with this lens, the bokeh/blur you can get in your background is so smooth and beautiful. It's a tough lens to use if you're shooting a large family, because you have to be stepping so far back if you want to get all the members and all of their bodies in the frame, but if you're comfortable with the lens and are used to the distances of it, the look you can achieve with it is awesome.
Find more info on this lens at Amazon.com by clicking here.

Zoom Lenses:
Zoom lenses are great for their versatility because you are able to go from a 28mm to an 85mm by just twisting the lens. Some drawbacks, and reasons that prime lenses are so popular, is that zoom lenses are limited in the aperture widths the offer, they are heavier, and thus require a faster shutter speed. But many of them will come with Image Stabilization, which is a feature that is used to battle the hand-shake that accompanies heavier lenses. The price of a zoom lens with a wide-aperture capability and IS, is very expensive compared to what you can get a prime lens for. So the big question is which type of lens do you prefer. Me? I like both for different reasons, so I don't really have a clear stance on this debate. However, I have put more money into investing in my zoom lenses, as they are all L-series lenses, and I haven't yet purchased any L-series prime lenses, so maybe I lean a bit more toward the zoom lenses. But even the less expensive, non-L-series prime lenses I have are great lenses, so again, it just depends on your needs!

24-105 IS 4L:
I love this lens for outdoor shooting. Being able to go from shooting a family with the wide-range distance and getting a ton of sky and landscape, to then zooming in on just their faces is awesome. The drawback is that I don't personally like to use it indoors, due to the limitation of the f/4 aperture. And this also means that even with outdoor shooting, you're not going to get the compression and bokeh that you would get from the 85mm 1.8. But sometimes, depending on what my focus is, I'm ok with that! I'll often get a couple shots with this lens that incorporate the environment, and then I'll put on another lens to focus on the facial portrait part of the session.
Find more info on this lens at Amazon.com by clicking here.

70-200 IS 2.8L II:
This lens is amazing for the quality of images it produces. The compression and bokeh is stunning, and the versatility of going from 70mm to 200mm is very convenient. The drawback to this lens is that it is super heavy! So it's not practical for everyday shooting with one's family. And it's also very expensive. But for professional work like portraits and weddings, this lens is pretty top notch and I do highly recommend it. 
Find more info on this lens at Amazon.com by clicking here.

24-70 2.8L II:
This lens also produces awesome quality images. Since I love my 70-200, but also love shooting wide, I bought this lens to fill in the gaps. It allows me to get those wide angle shots while maintaining the same quality image and same f2.8 capability of my 70-200. These lenses are a great pair together. But like the 70-200, it is a very pricey lens. But I've found it to be an awesome addition to my lens collection. 
Find more info on this lens at Amazon.com by clicking here.

As you can see, there are lot of lenses I love, and finding the right lens depends a lot on what your needs are. But I hope this list of my personal favorites helps answer some of the questions I get about my lenses. I'm hoping to continue to add to my lens collection, so check back to find my updates as I continue expanding my collection. :)