First of all, I [name]LOVE[/name] your list! Almost all of my favorite names are incorporated in some way in these combos. In fact, I think it’s more the combos that need a little work. The flow is sometimes off and the styles can contrast a bit as well. As for the two middle names, while I don’t see myself using two, I think it’s nice and if it flows with your surname, it would be fine.
[name]Violet[/name] [name]Helena[/name] [name]Esme[/name] / [name]Violet[/name] [name]Matilda[/name] [name]Ruby[/name]- [name]Violet[/name] [name]Matilda[/name] [name]Ruby[/name] seems to have a better flow but I love [name]Violet[/name] [name]Helena[/name] more. [name]Esme[/name] doesn’t seem to fit with [name]Violet[/name] [name]Helena[/name] though. What about [name]Violet[/name] [name]Helena[/name] [name]Pearl[/name] or [name]Violet[/name] [name]Helena[/name] [name]Beatrice[/name]? By the way, [name]Violet[/name] and [name]Ruby[/name] being in the same name kind of bother me as they’re both colors in a way.
[name]Alice[/name] [name]Matilda[/name] [name]Piper[/name]- I love [name]Alice[/name] [name]Matilda[/name] but [name]Piper[/name] seems to be a glaring contrast in style. Instead, what about [name]Alice[/name] [name]Matilda[/name] [name]Violet[/name], [name]Alice[/name] [name]Matilda[/name] [name]Ruby[/name] or [name]Alice[/name] [name]Matilda[/name] [name]Lark[/name]?
[name]Nora[/name] [name]Clementine[/name] [name]Ruby[/name]- [name]Nora[/name] is a little too cutesy for my taste as a stand-alone name. I prefer [name]Eleanor[/name]/[name]Eleanora[/name] nn [name]Nora[/name]. [name]Eleanor[/name] [name]Clementine[/name] [name]Ruby[/name] sounds wonderful. What about [name]Eleanor[/name] [name]Georgia[/name] [name]Beatrice[/name], [name]Eleanor[/name] [name]Penelope[/name] [name]Pearl[/name] or [name]Eleanor[/name] [name]Matilda[/name] [name]June[/name]?
[name]Elodie[/name] [name]Beatrice[/name] [name]Pearl[/name] ([name]Didi[/name] or full name)- [name]Elodie[/name] is pretty but I much prefer the sophisticated elegance of [name]Eloise[/name], which feels more classic and whimsical to me. [name]Beatrice[/name] [name]Pearl[/name] is beautiful though. What about [name]Eloise[/name] [name]Beatrice[/name] [name]Pearl[/name], [name]Penelope[/name] [name]Beatrice[/name] [name]Pearl[/name] or [name]Violet[/name] [name]Beatrice[/name] [name]Pearl[/name]?
[name]Eloise[/name] [name]Penelope[/name] [name]June[/name] ([name]Lola[/name] or full name)- I prefer [name]Eloise[/name] without a nickname as it is so beautiful on its own. However, the nn [name]Ellie[/name] would be my pick if I had to choose. [name]Lola[/name] feels a bit like a stretch to me. The combo itself is sweet, though I’m a bigger fan of [name]Jane[/name] or [name]Mae[/name] to [name]June[/name]. What about [name]Eloise[/name] [name]Clementine[/name] [name]Ruby[/name], [name]Eloise[/name] [name]Penelope[/name] [name]Pearl[/name], [name]Eloise[/name] [name]Matilda[/name] [name]Ruby[/name] or [name]Eloise[/name] [name]Emmeline[/name] [name]Lark[/name]?
[name]Emmeline[/name] [name]Georgia[/name] [name]Lark[/name]- I think [name]Emmeline[/name] is beautiful but it isn’t my favorite. The same goes for [name]Georgia[/name] and [name]Lark[/name]. Paired with other choices though, all three could be rendered absolutely gorgeous. What about [name]Helena[/name] [name]Emmeline[/name] [name]Lark[/name], [name]Emmeline[/name] [name]Beatrice[/name] [name]June[/name], [name]Emmeline[/name] [name]Alice[/name] [name]Matilda[/name] or [name]Alice[/name] [name]Emmeline[/name] [name]Pearl[/name]?
My favorite of your pre-existing combos would have to be [name]Eloise[/name] [name]Penelope[/name] [name]June[/name] because it flows the best aloud. Now to the boys! 
[name]Leo[/name] [name]Sebastian[/name] [name]Felix[/name]- I love all these names (especially the first two) but think they’re a bit too much to carry all together. [name]Leo[/name] [name]Sebastian[/name] is divine but [name]Felix[/name] adds just too much more energy and sounds. I think something more classic and well-used would work as the second middle. What about [name]Leo[/name] [name]Sebastian[/name] [name]George[/name], [name]Leo[/name] [name]Sebastian[/name] [name]Henry[/name], [name]Leo[/name] [name]Sebastian[/name] [name]Drake[/name] or [name]Leo[/name] [name]Sebastian[/name] [name]Charles[/name]?
[name]Jasper[/name] [name]Sullivan[/name] [name]Drake[/name]- [name]Jasper[/name] is great and [name]Sullivan[/name] is nice as well. I’m not a huge fan of [name]Drake[/name] but it works in the flow of the name. The flow is excellent but I think [name]Jasper[/name] could become much better when complimented with other names. What about: [name]Jasper[/name] [name]Everett[/name] [name]Felix[/name], [name]Jasper[/name] [name]Harrison[/name] [name]Oscar[/name], [name]Jasper[/name] [name]Atticus[/name] [name]Drake[/name], [name]Jasper[/name] [name]Maxwell[/name] [name]Jude[/name] or [name]Jasper[/name] [name]Elliott[/name] [name]George[/name]?
[name]Felix[/name] [name]Everett[/name] [name]Oscar[/name]- I think all the names are great (not my favorites though) but this combo isn’t doing much for me. What about [name]Oscar[/name] [name]Atticus[/name] [name]George[/name], [name]Felix[/name] [name]Augustus[/name] [name]Roman[/name], [name]Lucas[/name] [name]Everett[/name] [name]Poe[/name] or [name]Everett[/name] [name]Maxwell[/name] [name]Oliver[/name]?
[name]Milo[/name] [name]Harrison[/name] [name]Drake[/name]- I think this is my least favorite of your combos. [name]Milo[/name] has always felt a bit soft to me, [name]Harrison[/name] trendy and as I mentioned before, I’m not a fan of [name]Drake[/name]. I’ll try incorporating these names into other combos. What about [name]Charles[/name] [name]Milo[/name] [name]Harrison[/name], [name]Milo[/name] [name]Augustus[/name] [name]Jude[/name], [name]Elliott[/name] [name]Harrison[/name] [name]Jude[/name] or [name]Milo[/name] [name]Maxwell[/name] [name]George[/name]?
[name]Charles[/name] [name]Oliver[/name] [name]Felix[/name] ([name]Charlie[/name])- I love [name]Charles[/name] and [name]Oliver[/name]! They’re also great together: [name]Oliver[/name] [name]Charles[/name] works well too. However, the flow of [name]Charles[/name] [name]Felix[/name] and their similar endings are bothering me a bit. What about [name]Charles[/name] [name]Elliott[/name] [name]George[/name], [name]Charles[/name] [name]Everett[/name] [name]Poe[/name], [name]Charles[/name] [name]Oliver[/name] [name]George[/name], [name]Charles[/name] [name]Elliott[/name] [name]Henry[/name] or [name]Charles[/name] [name]Maxwell[/name] [name]Henry[/name]?
[name]Henry[/name] [name]Atticus[/name] [name]George[/name]- I love this one! Enough said. Well, actually I’ll give other options just in case. What about [name]Henry[/name] [name]Elliott[/name] [name]Roman[/name], [name]Henry[/name] [name]Augustus[/name] [name]George[/name], [name]Henry[/name] [name]Everett[/name] [name]Jude[/name], [name]Henry[/name] [name]Sebastian[/name] [name]Jude[/name] or [name]Henry[/name] [name]Atticus[/name] [name]Jude[/name]?
[name]Lucas[/name] [name]Elliott[/name] [name]Roman[/name]- This isn’t my favorite just because I like other combos more and [name]Roman[/name] isn’t a favorite of mine. What about [name]Lucas[/name] [name]Maxwell[/name] [name]Jude[/name], [name]Lucas[/name] [name]Sullivan[/name] [name]Jude[/name], [name]Lucas[/name] [name]Everett[/name] [name]Leo[/name], [name]Elliott[/name] [name]Augustus[/name] [name]Poe[/name] or [name]Elliott[/name] [name]Oliver[/name] [name]George[/name]?
[name]Oliver[/name] [name]Augustus[/name] [name]Poe[/name]- [name]Oliver[/name] is great! [name]Augustus[/name] is nice too, though not one of my favorites. [name]Poe[/name] strikes me as a bit sudden and offbeat compared to the rest of the combo but maybe that’s a good thing
What about [name]Oliver[/name] [name]Lucas[/name] [name]Poe[/name], [name]Oliver[/name] [name]Sullivan[/name] [name]Jude[/name], [name]Oliver[/name] [name]Sebastian[/name] [name]Jasper[/name], [name]Oliver[/name] [name]Elliott[/name] [name]Drake[/name] or [name]Oliver[/name] [name]Henry[/name] [name]Roman[/name]?
[name]Maxwell[/name] [name]Everett[/name] [name]Jude[/name] ([name]Max[/name])- [name]Maxwell[/name] is a cool name: unfortunately it seems many agree. It’s rising in popularity thanks to the spotlight of celebs and I can see it vaulting to the top of the charts soon. So if popularity is a problem for you, I would confine [name]Max[/name] and his variants to the middle. [name]Everett[/name] is cool, just not one of my favorite. It does flow well with a lot of names though: a bonus. [name]Jude[/name] is a great, stoic name that stays strong and handsome through thick and thin. It’s not my ideal choice for a first name but I think it’s great in the middle name spot. What about [name]Everett[/name] [name]Augustus[/name] [name]Jude[/name], [name]Maxwell[/name] [name]Jasper[/name] [name]Drake[/name], [name]Maxwell[/name] [name]Sebastian[/name] [name]Poe[/name], [name]Maxwell[/name] [name]Leo[/name] [name]Sebastian[/name], [name]Maxwell[/name] [name]Henry[/name] [name]Atticus[/name] or [name]Maxwell[/name] [name]Oliver[/name] [name]Lucas[/name]?
My favorite pre-existing combo for the boys is [name]Henry[/name] [name]Atticus[/name] [name]George[/name], which I love!
Good luck! 