I'm not going to vote on this, because I think it depends too much on the person. If they're a little wary of acceptance, go for a tartan traditional; it just screams "I'm a kilt, darn it, not a skirt!". If money is more concerning, maybe a contemporary would be better just to get the hang of it. Of course, personal taste might sway the decision one way or the other, anyway...

For me personally, traditional is the way to go. I probably won't ever own a contemporary (barring perhaps a knockabout SportKilt for lounging at home). I can appreciate UtiliKilts, et al., but they're just not for me. I prefer my kilts in tartan; I think they just look better and are more visually interesting/attractive. But someone else might think differently