So [name_m]Oliver[/name_m] is the top of my list for boys. I love it as just [name_m]Oliver[/name_m] (not [name_u]Ollie[/name_u]/[name_u]Olly[/name_u]/Oli) And I also love [name_m]Connor[/name_m]. Personally I think that [name_m]Connor[/name_m] goes well but what does everyone else think about [name_m]Oliver[/name_m] [name_m]Connor[/name_m] as a combo? I would put a less ‘classic’ name with it because there are too many [name_m]Oliver[/name_m] [name_u]James[/name_u]'.
In my opinion I wouldn’t use this combo only because they both end in R and Im picky about that. I would suggest something that flows a little better. What about…
[name_m]Oliver[/name_m] [name_u]Jude[/name_u]
[name_m]Oliver[/name_m] [name_m]Gage[/name_m]
[name_m]Oliver[/name_m] [name_u]Blaze[/name_u]
[name_m]Oliver[/name_m] [name_f]Cadence[/name_f]
[name_m]Oliver[/name_m] [name_u]Dean[/name_u]
[name_m]Oliver[/name_m] [name_u]Dane[/name_u]
[name_m]Oliver[/name_m] [name_u]Kai[/name_u]
[name_m]Oliver[/name_m] [name_u]Reese[/name_u]
[name_m]Oliver[/name_m] [name_u]Wade[/name_u]
[name_m]Just[/name_m] to name a few
I would choose a different middle name. [name_m]Oliver[/name_m] [name_m]Connor[/name_m] works, but to my ear does sound a bit awkward.
Yeah, I have to agree with the others – the repeated “r” trips it up a little bit.
My first boy will be [name_m]Oliver[/name_m] [name_m]Henry[/name_m], classic. But if you want to shake things up a bit, try these middles:
[name_m]Grayson[/name_m] (I thought [name_m]Jason[/name_m], but for some reason, [name_m]Grayson[/name_m] just sounds better)
[name_m]Christophe[/name_m]
[name_u]Douglas[/name_u]
[name_m]Ferris[/name_m]
[name_m]Franklin[/name_m]
Florenz (not a popular choice, but an intriguing one for fans of early American Broadway)
[name_m]Humphrey[/name_m]
[name_m]Kipling[/name_m] (nn [name_m]Kip[/name_m]?)
[name_m]Hugo[/name_m]
[name_m]Harvey[/name_m]
[name_m]Gilbert[/name_m]
[name_m]Hardy[/name_m] (if you’re a major fan of the comedian)
Gresham
[name_m]Creed[/name_m]
[name_m]Judah[/name_m]
[name_m]Kingston[/name_m]
[name_u]Lawrence[/name_u]
[name_u]Lennox[/name_u]
[name_u]Macon[/name_u]
[name_m]Maddox[/name_m]
[name_m]Maksim[/name_m]
[name_m]Maxwell[/name_m]
[name_m]Samson[/name_m]
[name_m]Silas[/name_m]
[name_u]Shane[/name_u]
[name_m]Winston[/name_m]
[name_u]Tatum[/name_u]
[name_m]Titus[/name_m]
[name_u]Tate[/name_u]
I think they have too many of the same sounds in them. Both have the short o sound and end in r. I would keep looking.
I like it!
[name_m]Oliver[/name_m] [name_m]Connor[/name_m] is a bit too much in my opinion.
My son is [name_m]Oliver[/name_m] [name_m]Eli[/name_m] 
[name_m]Oliver[/name_m] [name_m]Colin[/name_m]
[name_m]Oliver[/name_m] [name_u]Corbin[/name_u]
[name_m]Oliver[/name_m] [name_u]Carson[/name_u]
[name_m]Oliver[/name_m] [name_m]Warren[/name_m]
[name_m]Oliver[/name_m] [name_u]Brennan[/name_u]
[name_m]Oliver[/name_m] [name_u]Shea[/name_u]
[name_m]Oliver[/name_m] [name_u]Aiden[/name_u]
Not perfectly, but definitely usable, especially as the two names you love. Handsome names.