[name_m]Hi[/name_m] there.
Here are my thoughts-
Jake-I think that [name_m]Jake[/name_m] has a cool vibe, but I really do find it too nick-namey on its own. It feels like it needs to be a nn for [name_m]Jacob[/name_m]. Which I find super handsome personally. [name_m]Jacob[/name_m] [name_m]Malcolm[/name_m] is pretty good. I don’t love the flow of [name_m]Jake[/name_m] [name_u]Hayden[/name_u] that much, because of the repeating long ‘a’ sounds. Probably not a big deal.
Jack-This feels more like it works as a full name than [name_m]Jake[/name_m]. It’s charming & fun & timeless & sounds great w/your ln. It’s pretty popular; especially if you add in all of the Jacksons. [name_u]Jack[/name_u] [name_m]Malcolm[/name_m] [name_u]Hayden[/name_u] sounds really nice.
Calvin-This is really cute & quirky & old fashioned but feels fresh. I love the nn [name_u]Cal[/name_u] mostly. I don’t love how CalviN HaydeN sounds, but it’s not awful.
James-This is a another nice timeless classic. [name_u]James[/name_u] [name_u]Hayden[/name_u] isn’t as good as [name_u]Jack[/name_u] [name_u]Hayden[/name_u], but it’s not a problem. It’s pretty common, but for a good reason.
Benjamin-This has the same ‘n’ issue as [name_m]Calvin[/name_m], but it’s a great name. Fairly common, but for a good reason. I think that [name_u]Benjamin[/name_u] [name_u]Joseph[/name_u] flows better than [name_u]Benjamin[/name_u] [name_m]Alan[/name_m].
Callum-I love [name_u]Callum[/name_u] [name_u]Joseph[/name_u]. Very handsome & sounds much better w/your ln than [name_m]Calvin[/name_m]. A bit softer & also a kind of sporty than [name_m]Calvin[/name_m]. I like [name_m]Calum[/name_m] more, but [name_u]Callum[/name_u] is more popular.
Leo-This is cute & quirky & simple & vintage. I wouldn’t say that it’s trendy since it’s an old fashioned name, but it is getting popular really fast. So, I don’t know. Fun name though, & [name_u]Leo[/name_u] [name_u]Joseph[/name_u] [name_u]Hayden[/name_u] sounds awesome.
Miles-This one is kind of like [name_u]Leo[/name_u]. It’s old fashioned, but I’m suddenly hearing it everywhere. I’m not a huge fan for some reason, but it’s a nice name & [name_u]Miles[/name_u] [name_u]Joseph[/name_u] [name_u]Hayden[/name_u] sounds good.
Owen-Very sweet & kind & slightly outdoorsy name. I like it a lot. It’s a bit popular, but not too bad. [name_u]Owen[/name_u] [name_m]Malcolm[/name_m] is very handsome, even though [name_u]Owen[/name_u] [name_u]Hayden[/name_u] doesn’t flow perfectly.
Lachlan-Same ‘n’ issue, but I’m starting to think that that doesn’t bother you. It gives me a similar vibe as [name_u]Owen[/name_u], but less popular.
Caleb-I don’t love this w/your ln, but it’s fine. It’s a name that I should like, but it doesn’t excite me that much.
Theo-Same feelings here as [name_u]Leo[/name_u]. Although I prefer it as a nn for [name_m]Theodore[/name_m].
Jude-Ooh, I love [name_u]Jude[/name_u]. [name_u]Jude[/name_u] [name_m]Malcolm[/name_m] is gorgeous.
Cullen-I really like this in theory, but it’s a little hard to say. I think that people will just mistake it for [name_m]Colin[/name_m] a lot.
Max-I love [name_u]Max[/name_u]. It’s really punchy yet classic. Kind of popular, but for a good reason. [name_u]Max[/name_u] [name_u]Hayden[/name_u] sounds perfect.
Jonah-I like this. It’s sweet & kind & sounds strong at the same time. [name_u]Jonah[/name_u] [name_m]Malcolm[/name_m] sounds nicer in my opinion.
To answer your question, my favorite in general is probably [name_u]Jude[/name_u]. But [name_u]Max[/name_u] is my favorite that also sounds good w/your ln. [name_f]My[/name_f] least favorite is [name_u]Miles[/name_u], but I don’t dislike it that much.
[name_f]Hope[/name_f] this helps. 
both timeless names and not extremely common! plus both combos flow great