[farfilo]

I have to say that the grey silicon olives are unbeatable to me with the spit / lollipop treatment.
The sealing is tight and to me the shape is the most comfortable and easy.
If you make the olives a little wet with spit before inserting (don't be disgusted, it's your stuff) and after inserting you simulate 5 seconds of chewing, the result will be stunning.
 
Hope this helps... even 2 years after the starting of the thread

 

[Mooses9]

also the silicone olives here, ive been rockin them for over 7 years with various shure earphones,those arealways my go to tips. never really use the comply tips.

 

[plmtr]

Been through SE530PTH, SE530 and currently SE535 limited edition. I've definitely done a bit of dancing around with the tips over the years, usually settling back on the 'default size' black foam tips for my med to small ear canals.  I've just tried the great tip from here to slice my triple-flanges down to double-flanges and I've got to say that was a fantastic idea. I've always felt that these ultimately provided the finest accuracy, clarity and isolation but a compromise in comfort for my ears. Now fitting quite comfortably with the modification :-D
 
It's a really close call though with whatever the largest black foam tips you can compress in to your ear and get a good seal. I still find these to have ultimate comfort and even a bit more isolation (and consequently a bit more head bass sound).
 
I'm going to keep both these options on hand depending on how I'm feeling.

 

[stereoscopic]

Having just acquired at set of SE535s I though I would add my 2p as this is the first thread that came back on a Google search of 'best tips for Shure SE535'
 
I couldn't get a good fit with the original olives that were fitted when I got them, although they appeared to seal correctly, they were uncomfortable.

The white tri-flange tips are OK, but I had to cut about 5mm off the length as they appeared to bend on inserting and blocked the sound occasionally.
 
Then I tried the large grey tri-flange tips from my Etymotic ER4-PT/S and BINGO - perfection.
Superb fit, perfect seal, uber comfortable (for me), and literally tonnes of tightly controlled bass. I could easily sleep on them.

 

[Peter Hyatt]

I am trying to figure out what is best...I am not certain of my size. 
 
The rubber has smaller opening than the sponge type.  
 
What is the difference in sound? 
 
I understand that ambient noise reduction and expansion work together, but is there one type better for sound, with the other type better at noise reduction, hence, impacting sound?  
 
Generally, is an average size male 5'9" without a humongous cranium (average size head) with average size ears a 'medium' in these things?  
 
I go back and forth from medium to large foam collapsing type, but I am not sure which is best.   
 
Is the size that they come already attached medium?  I ask because I bought these second hand and have new sleeves. 
 
I love the sound!  

 

[s1rrah]

 
I go back and forth from medium to large foam collapsing type, but I am not sure which is best.   
 
Is the size that they come already attached medium?  I ask because I bought these second hand and have new sleeves. 
 
I love the sound!  

 
The SE535's come with "medium" black olive tips installed on them ...
 
And like yourself, I'm pretty average when it comes to head/ear size ... and I've always found the "medium" foam tips (black olives) to work best for me ...
 
The large works for me too but the mediums offer the best insertion depth and isolation ...

 

[Peter Hyatt]

   
The SE535's come with "medium" black olive tips installed on them ...
 
And like yourself, I'm pretty average when it comes to head/ear size ... and I've always found the "medium" foam tips (black olives) to work best for me ...
 
The large works for me too but the mediums offer the best insertion depth and isolation ...

Thank you.  
 
I now have the medium foam in, which goes a bit deeper than the large, and may be more comfortable. 
 
What of the size of the hole?  Why are the rubber (silicon?) hole size smaller?  
 
I do love the sound and think I will become used to the comfort over time.