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Looking for the perfect Nikon portrait lens

What kind of portraiture?

For decades, I’ve used the 85/2 and 135/3.5 depending on the type and goals. Been happy with the results. As you must know, it’s not as much about the gear as it is about the
 
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I have always liked the 85mm 1.8 H. I had a brief time with the 85 f2.0 and didn't like it and went back to the 85 1.8. I also like the 105mm 2.5 early version too. Outdoors the 135mm 2.8Q was good.
 
For me it will always be the 105mm f2.5 AIS. I'll second the 135mm f2.8 Q.C. for a second choice. Some say the older 135mm f3.5 Q is better, but I have both and between the two the 135mm f2.8 Q.C. wins hands down.
 
I think the 50/1.2 is magical for portraiture. I prefer a little context in my images, so the longer alternatives don't appeal to me.
With that said, an old seasoned Nikkor-H 85/1.8 (ai converted if necessary) would be my next choice.
 
Of the choices you list, I'd have to go with the 105/2.5. I find 85mm "too environmental" (brings in too much of the surroundings for a proper portrait), and the one copy of the 85/2 I tried out was underwhelming optically. The 135mm focal-length always feels cramped to me (though to be fair 135mm along with 50mm are probably just focal-lengths I don't bond well with). The 100/2.8 series E is a great, super compact lens which can be found for sub $100, but the 105/2.5 is just a much better lens. All the 105/2.5 versions have their benefits, but my favourite is the AiS with built-in hood. The early Sonnar version (with silver snout) is also quite interesting, with the classic solidity of an older Nikkor, and can be had for pocket money.
 
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feel free to add

If opening up the choices, and your budget allows, the 105/2 DC is an amazing portrait lens both optically and mechanically. The defocus feature is quirky and does not play well with AF on most bodies, but otherwise the DC is perhaps Nikon’s best portrait performer. There's a 135/2 DC as well, but it's bigger than the 105/2 DC, and supposedly not quite as good, but as said I don't bond with 135mm so I never tried it.

There’s also the 105/1.8, which I do love as well, but it doesn’t really outperform the f/2.5 (except one stop faster of course) and for the premium you pay for the f/1.8 you can probably pick up a DC.
 
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For me the question usually is which focal length do I prefer, then AF or MF, and only after that which specific lens. It also depends if I‘m looking for a modern look or a softer one, and b/w or color.

Personally I find everything over 90mm flattens out the image too much, so I prefer something in the range 50mm to 80mm.

On the MF side, the 50mm f/1.2 AIS is lovely as Niroplait mentioned above (very soft snd painterly at 1.2 and sharp from f/2 up)
The Zeiss ZF 50mm f/1.4 is also special.
The Zeiss ZF 50mm f/2 is very sharp and high contrast if you prefer that look.

I find the 85mm AIS lenses solid but nothing exciting.
The Zeiss ZF 85 f/1.4 has a bit more bite.
The 105mm f/2.5 is great but too long for me.

On the AF side, the interesting ones are the 85mm f/1.4 AF-D and 105mm f/2 DC, but i find them somewhat fuzzy wide open and expensive.

The 50mm f1/4 AF-D and all the G lenses are ok but again not very special.
The Sigma Art 50mm and 85mm f/1.4 are great if you are looking for clean and modern rendering.

All that said, those are minor differences and lighting and environment will have much greater impact - as will switching to medium format, which I much prefer for portraits.







Afaik there is no 80mm f/2 from Nikon.
 
I have used the 85 1.4 AF-D for years and think it's an excellent lens. Downsides are the relative softness at 1.4 (very sharp at f2) and the color fringing when shot wide open with back lighting. That being said, in many cases this lens looks amazing at f1.4.

If you want AF this lens is very accurate and fast
 
I'll toss another one in to the list. While i'm not really into portraits I used this one mainly for clinical photography it is very sharp and can also be used for macro either auto focus or manual and fits f mount digital as well. The AF Micro Nikkor 105 2.8-D An example from years ago on tri-x 400 35mm.

 
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Good suggestion, can be had at a reasonable price
 

I don't have the AF-Micro Nikkor, but do have the MF Micro Nikkor 105/2.8, and can compare it to my 105/2.5 AiS. The Micro Nikkor is great for its intended purpose, and is clinically sharp, especially stopped down. However, I was never pleased with its rendering for Portrait and Landscape photography, particularly the OOF background rendering (what we now call Bokeh, but I didn't know that term back in the 80's). I rarely use my Micro Nikkor anymore, because I use the 105/2.5 for portraits and a Voigtländer 125/2.5 APO-Lanthar for my on-camera macro shots. That being said the older D version of the AF-Micro Nikkor is available quite cheaply, and is by all accounts a great lens, so worth considering for a multi-purpose solution.
 
I think it depends on how much working distance you have, studio vs environmental ect, lighting and your preface for how tight you want your shots. If you are going to shoot in a studio the 85 is a great lens, if you plan on traveling and shooting outdoors then the 105 2.5 is a stellar lens. Other option, if you want to soften your shots without going to a soft focus lens, then a 2X teleconverter on a 50mm lens or a early zoom in the 35 to 85 mm range. Not as soft as a soft focus lens, but not as sharp as a prime.