Derrick,
Ask most any of us to have carried for any length of time (years) and it’s a good bet that they will have a drawer full of holsters that either didn’t work or eventually found something better. Best bet to begin is to determine and settle on a firearm, next location (easy access from strong hand) to carry. both of these are needed to start the process of muscle memory. Inside or outside waistband common dress. Yep it’s a never ending story for awhile that’s why settling on a location, firearm IWB or OWB, at least narrows it down. Opps forgot activity to determine if retention is required.
A few hints are don’t get any more retention then you need it’s just something to forget when the poop hits the fan, Kydex is as stiff as the gun on skin, get something with a back plate/sweat guard guns parts protrude and poke, must have a GUN belt your normal belt will die quickly it might even break at the wrong moment, service size pistols are a pain to conceal but most people still won’t see you carrying, stay away from uncle mike neoprene holsters. For the wife I won’t start but my wife gives classes for the ladies on holsters, carry locations and styles.
Bill
Being someone who can’t carry(Stupid Maryland gun laws) my only suggestion is to possibly take a course in holster draw say from an NRA instructor. At the very least you may get some instruction on what your searching for.
There are a variety of factors to take into consideration… holster type, holster material, carrying style, body type and clothing to name a few. Clothing itself is a touchy subject. I wear my pants below the gut which is slightly lower than my waist. Match that with a poor belt and I’m doomed. I look like a cowboy with a 6 shooter and saddle bags.
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Get a strong sturdy double stitched belt. Realtree or CarHartt are inexpensive brands with many different styles.
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Find a retailer that will allow you to try on holsters. I had a few hours to burn yesterday and went to Cabela’s. No intentions on buying anything, so I told my wife, I purchased my first IWB holster. Of course, only after I was able to try it on gun and all. I am on the move all day every day. Although I can’t carry at work, I do as soon I get home. On and off with IWB has made life easier. Not to mention, it holds closer, tighter and more secure. The ease of ordering online often gets in the way when making such personal purchases. @Jerzees said it best, “like finding best shoes.”
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Try your best to stick with an everyday holster for at least 3 months. Seasonality may dictate a change depending on weather.