I'll echo what flechero said about the value of a quality gunbelt. The analogy is spending $2,000 on a rifle, but then only $200 for a scope: you've crippled a high-performing tool with an inferior add-on.
That said, I'd also recommend starting your search with some very basic questions...likely won't completely save you from the "retired holster drawer" that many of us have, but may help. Some may suggest starting with your normal style of dress; that has some merit if your work circumstance requires a particular dress code (e.g., a corporate attorney who wears a suit six days a week). However, I'd tend to start with position of carry first.
Carry on the hip actually has a lot of variances. Start with where you wear your belt and shoulder flexibility. For example, if somewhat high-waisted and have shoulders that may not be as flexible as they could be, you probably won't want to consider a straight-drop holster at the four o'clock position (assuming you're right-handed). Gonna be really tough to get the gun out smoothly.
The potential for moving the holster around on hip-carry before you find your "sweet spot" is one reason to consider a holster that has an adjustable cant. Typically, hip-carry involves positioning the holster between 5:00 and 3:00, with 3:00 being directly to the side of the hip. That's where I prefer to carry; I'm relatively wide-shouldered and have the aforementioned lack of Gumby-like shoulder flexibility.
Another option for on-belt carry is in the appendix position at approximately at 1:00 with a rearward cant. It's generally thinner folks who can get away with this position; also favored by some women because it removes the flair of the hips from the concealment equation, often an issue with hip carry at 3:00 or 4:00. Appendix carry actually has some mechanical and tactical advantages. But it's eschewed by a lot of guys because of the muzzle orientation as well as that, IWB, it doesn't accommodate service-length barrels easily.
Another belt option is small-of-back carry, something I've always argued against: the exact reason appendix carry can offer mechanical and tactical advantages is the reason small-of-back carry is disadvantageous.
A shoulder holster is another option, but it sounds as if you're looking for on-belt carry.
The next determination would be Outside Waistband Carry, or Inside Waistband Carry. For comfort, OWB always rules, but it offers fewer options to dress around the gun if you plan to keep it concealed. I prefer IWB for concealability, and have come to prefer Kydex-leather hybrid holsters for the purpose. All-leather IWB holsters need to be heavily reinforced to keep them from collapsing once the gun is drawn, therefore making safe reholstering very difficult. My EDC is a Comp-Tac MTAC. The leather backing provides the next-to-body-comfort of an all-leather holster, with the rigidity and shape retention of the Kydex shell.
One other tip if you choose IWB. If you don't wear an undershirt now, you'll probably want to consider starting to do so. I've seen some strange, cloth IWB holsters that I'd never even consider, so that means the surface otherwise contacting your body will be leather or some combination of other non-cloth materials...and possibly part of the butt of the gun, depending on gun and holster configuration and where you're carrying. That skin contact is a no-go for me. Never wore undershirts when I was younger, but started doing so when I began carrying IWB; can't leave home without it.
If you have any friends who will let you try their holsters, it's not a bad idea. Doesn't have to be your exact firearm, just one that is similar in size. Especially friends who have that drawer with two dozen retired holsters in it.
You may not find the exact holster you think would suit you, but a weekend visit for pizza and an hour of trying different holsters might at least help you winnow out the styles and types you know you don't want to consider. That could go a long way to preventing you growing your own drawer of retired holsters.