I definitely think of Leland as an older name.
But I don't think it's quite turned the corner from "old man" toward "distinguished." When I think of names like Henry or Theodore or Edmund, they evoke sort of Edwardian splendor. I think Leland is a little uneasy in that crowd — it doesn't sounds as sophisticated.
Which is ridiculous. I mean, it's an old English name that should sound right at home with those other names. But it does have a more rural vibe to it, at least to my ear. I would class it with Chester — a name very much appropriate to that era, but not quite the right sound for the modern revival.
Of course, it's a family name, so the style considerations are secondary. I definitely think Leland and Henry over Leland and Rylan.