This is really random but does anyone else have issues with earbuds falling out or hurting their ears? I feel like I have small ears and I’m looking for a good pair of in-ear buds. Wired or wireless. I have a nice pair of over-ear headphones but I need something more professional for hosting interviews via Webex.
Are there custom in-ear headphones?
Also, what would be a good pair of wireless in-ear headphones for small ears?
Thanks again!
My ears have different inner shape, therefore, when right fits, left don’t and vice-versa.
What I found as best option, although not the best soundwise, was these sport earphones, that are hanged from the outer ear. They don’t fit perfect, but they don’t fall either.
(not recommendation, just an example)
You need a pair with microphone or without? What’s your budget?
Some companies will make you custom IEMs if you give them scans of your ears or you have them make molds, but it gets expensive really quickly (sending scans is the cheapest, having a company take a mold is the most expensive thing).
I have been using QCY T5 for some time, for this price they are ok. They have three sizes of ear tips, so you can probably fit something to your ear. I use the medium size and it’s ok, but what does a small ear mean is a relative term. 
QCY T5 is one of the most comfortable truly wireless earphones on the market .
You have some choice for CIEM, but that would be expensive. But I am in the same camp as you for IEMs often hurting my ears. But ATH-IM02 (most recent model ATH-LS200) are nice for me. Never hurted my ears and fit well, with the help of Spinfit tips.
You could go with the LS70 or LS50 for the cheaper options, pretty much same shell.
When I went with my mother to get tested for hearing aids, the doctor offered to make me custom ear plugs for free. Being stubborn I declined, but I wonder if there might be some way of having custom pieces made that aren’t terribly expensive going that route.
Hearing doctors have to be well versed with the entire ear and have probably seen a lot of things while fitting hearing aids. Especially if it is for work and you have insurance then it could be worth looking in to if you don’t find any simpler solutions that suit you. Of course your local doctor may not be as nice, but you could always take a vacation to Jacksonville Beach.
First of all, try to use foam tips, they should fix it for you, if you want you can buy custom IEM’s, but those will cost a ton of money, so you could probably begin by buying something like KZ ZS10PRO or TIN T2 and trying different foam tips with them.
The best solution in terms of fitting will be a casting.
But you can also think of something like 3m ear plugs 
and drill a hole in them. I use them to sleep sometimes and they don’t cause pain or fall out so as a DIY project it might be good. They are soft and flexible, they deform themselves to the environment, so they sit quite firmly in the ear, and at the same time they are soft enough and have a low deformation pressure that they should not cause pain.
Or buy one with a hole intended for this purpose right away.
Or the 3M PELTOR EARbud2600N … or something similar that has foam tips, as these tips will probably be the most comfortable and shouldn’t fall out.
I like overears, because they’re quicker to put on/take off, a friend who’s into audio swears by “Fender PureSonic Wired Earbuds” for comfort (they’re around $/€/£ 40). Apparently he fell asleep with them and was freaked out when he woke up hours later and everything sounded weird, until he figured out he was still wearing them - but I haven’t tried them personally.