I've worn a handful of masks, but only ever used two full time..
Sly Profits - Great mask for comfort and protection, changing lenses is super easy, covers the neck, ears and forehead really well and I never in two years had an issue with steaming up outdoors or indoors. This was the first mask I ever bought after trying on Flexes, Events, i4's and Proto Axis'. The negatives for this mask are that you can't hear very well, and your voice is absorbed in the mouth piece. For communication this mask is sub-standard, and while they can be expensive, for someone new to paintball I would definitely say these should be in your list of masks to try!
JT Proflex/Empire E-Flex - I personally have two Proflexes, and I don't think I'll ever change. The ability to customise, the large variety of parts, the breathability are all fantastic. Unlike the Profits you can hear and be heard everywhere on the field. These really are the most comfortable mask I have ever worn. The downsides to the JT are lack of protection on the ears, which you can remedy with hard ears simply enough (See the yellow mask below), and the initial difficulty in changing lenses. The E-Flex, which is super popular with my team mates, has the empire quick change lense which essentially negates the only issue a new payer could have with the JT Proflex, and so, one of these two masks would be my top-most recommendation!
For those with Glasses, both of these masks are great, and have plenty of room for glasses underneath (even people who prefer larger frames like me!) I have a head on the larger scale, and while I frequently had these masks on a looser setting on the strap, I was always comfortable and never had problems with slips. In general you should ALWAYS try as many masks as possible, because everyone is different and everyone has their own preferences and needs.However, having tried many masks myself, I would recommend that you ensure these two masks are on your list of those to try!
These were my profits, my top recommendation for someone new or someone concerned with protection over communication
These are my two Proflexes, my top recommendation for all round performance, customisation and competitive play.