I, like most guys, did my first contest raw... but there are plenty of guys who compete for the first time in gear.
Switching to gear is less about how long you have been powerlifting and more about how much of a foundation you have already built up. If your form sucks squatting raw, then when you have the suit there trying to push you around it's only going to get uglier..... With that said, my team has taken more than a few new lifters and had them being successful in gear within a few months.
When I made the switch I had hit 425-350-540 in a
powerlifting meet and was hitting ~500-385-550 in the gym. I switched in the fall, and my the following March I competed in gear and went ~745-450-600. I had a great time switching in to gear, never any problems. But I had a good foundation and I had a really good team to help me.
My suggestion..... find a team to help you out. If you go to any local meet you'll see the same guys there every year lifting half of what they should because they try to train alone and have no ****ing clue what they are doing.
If you decide to go for it yourself I'd say to start in a poly squat suit. Start with the straps down then as you get used to it start getting the straps up loose, then eventually tighter. Once you feel comfortable there most guys just cut off the straps and use the suit as briefs under a heavier poly or canvas suit. For shirts, start out with a LOOSE 2-ply. Once you get good at working the shirt you can start tightening it up. If you are benching with just one spotter please do it in the cage with safety pins set so you don't smash your face.
Either way, good luck. PM me if you need any help finding a team to train with. I know EVERYONE.