Hi there.
Ruby is so cute!
Here are my thoughts on the lists for a little brother:
Milo/Miles-These names are very different to me. Mainly just [name_u]Milo[/name_u] seems quirky & classic & more unique. And it goes better w/Ruby. I hear [name_u]Miles[/name_u] a lot a lot in my area, so I’m just a little bored w/it.
Elijah-This is a lovely name, but very over done as well. It’s a little fancy next to [name_u]Ruby[/name_u], but not a deal breaker.
River-As long as you don’t mind the two 'R’s, I really love this. It’s handsome & artsy & rugged & warm. It actually goes really well w/Ruby, even though they’re kind of different styles. Both nature-y, at least.
Elliot-I really like this, but prefer [name_u]Elliott[/name_u]. It looks more complete. [name_u]Elliott[/name_u] is smart & witty & handsome. It wouldn’t be my first pick w/Ruby, but it doesn’t clash.
Finn-I love [name_u]Finn[/name_u]. It’s probably my favorite from your list. It’s just so sleek, sporty, spunky, witty & charmingly boyish.
Owen-This is a really nice kind gentle yet outdoorsy & rugged handsome classic. It’s a little over done, but still a great choice.
Hudson-So, this name is really over done too. I hear it a ton in my area, & I just find it a little trendy & uninteresting. A few of your other choices are quite common too, but it doesn’t bother me as much when they feel old fashioned & popular, you know?
Alex-I think it’s fine, but not terribly exciting. I definitely would at least prefer [name_m]Alexander[/name_m] nn [name_u]Alex[/name_u].
Noah-A good solid classic, but just so over done that it doesn’t sparkle.
Simon-This is cute & goes well w/Ruby. Smart, quirky & old fashioned. Not terribly over done either, but simple & well known.
Oliver (nn [name_u]Ollie[/name_u])-So cute, but also very popular. Really nice w/Ruby though.
Theodore (nn [name_u]Theo[/name_u])-See [name_u]Oliver[/name_u]!
Henry-A super smart handsome lovable classic, but every little boy I meet is called this.
Patrick-I actually kind of love this name, even though it wouldn’t be my first pick w/Ruby. It sounds fine though. I don’t like [name_u]Pat[/name_u], & I’m not sure whether or not it’s unavoidable. But I do love Patch!
Peter-I love this. It reminds me of [name_m]Peter[/name_m] [name_m]Pan[/name_m] or [name_m]Peter[/name_m] Rabbit. Both fun associations.
Jack-Well, I love this name, but wouldn’t do it. [name_m]Jack[/name_m] [name_u]Ruby[/name_u]! The guy who shot [name_u]Lee[/name_u] [name_m]Harvey[/name_m] [name_m]Oswald[/name_m].
Oscar-I love this one. It’s handsome & hipster chic but still has vintage charm. Not too popular either.
Jacob-A beautiful classic, but also really over done, so I don’t know.
I’m not much help, since I basically like them all. But my favorite w/Ruby is [name_m]Simon[/name_m] or [name_m]Oscar[/name_m].
Hope this helps. 