Electronic tags belong on the ankle.
My first instinct was to be drawn to the Alpina, because it's more like a "real" pilot watch: the hands and the bolder hour markers are reminiscent of the original Luftwaffe models, and the arrow on the second hand gives it that "technical" look.
But. Actually, two "buts".
But (1): If you wanted an authentic flavour for a pilot watch, then I always point to the original five makers: Lange and Wempe, who no longer make pilot models, IWC who make them expensively, Stowa who make them similarly but at a low price, and Laco, who make the cheapest, but not quite to Stowa's quality. In this price range, I always point to the Stowa Flieger models. True, none come with an integrated bracelet, but they have a steel mesh bracelet option, or rubber, plus their own leather and croc choices - and that's just the OM offerings.
But (2): The Alpina is massive. And although I quite like that conical crown, on a 44mm case I think it's going to be a nuisance. You wanted a pilot that wasn't too pilot, and the bulk and styling cues of this make it a lot more showy, a lot more tool-like, and therefore a lot less versatile.
So, the Oris: at 41mm it's large for a dress watch, but I think it's smooth enough to work with a jacket at tie or casual wear just fine. The fussy details on the bezel you like or don't, and I don't love that it says "Big Crown" "Pro Pilot" on the dial. Feels like insecurity! But on its own merits, I like the proportions of it, that clean modern look of the hands, and the tidy beveled edge on that "big crown". I think it's inherently a nicer watch for an all-rounder. The smooth-edged bracelet on the Alpina looks nicer, but I think this will be a lot more wearable.