2 totally different boots IMO.
The Alden is more of a dress boot and I agree it is different enough from a wingtip that it is worth getting. I wear my Grant last #8 captoes and AE Cappuccino Bayfields a lot more than wingtip boots, but still almost always as dress boots.
The 744 I only wear casually. But I wear them a lot and sometimes in rough conditions without any issues at all. I wear them so much because I love how they fit and feel and part of that is because they are unlined. I will even wear them when fly fishing on small streams when I don't need to wade wet, and know I am going out to eat after. Yes they are paired with technical pants
They have always cleaned up fine when I needed them to and I have never had an issue with integrity of any part of them.
The 744 is a unique boot, at least in my eyes. You can always pick up a shell captoe dress boot, or at least with a little waiting you can. Something like the 744 not so much. January before last I spent a week in the Phoenix, AZ area and wore them every day. They handled town at night, light hiking in the desert and every thing in between perfectly. My girlfriends daughter was there from Indy and she has a Masters in Art and media sciences and works in those fields. One evening in the hotel room she came over and picked up one of my 744's and studied it for a bit then said these things are beautiful and a work of art. She asked if I could try and talk her boy friend into wearing boots like them. I told her she was on her own there LOL.
As to which one is correct I think a lot depends on your lifestyle. For me the answer is both, one is for play and the other for work.
How has the toe held up without structural reinforcement? I keep going back and forth on this one. Unfortunately I only have the funds for one of these since I'm also committed to the Alden x Epaulet Innsbruck.
The Alden's I could wear to work in bus casual, with a suit, or with jeans. The 744's look like a jean shoe only. Both look great to me. Trying to justify and prioritize. Uggh indecision!!!