Baby boy (likes Oliver, but not Oliver)

Boy.
I like Oliver, Jude and Milo but those are way too trendy. I really love Oliver but I suspect it's too popular (I live near SanFran). I hate realizing that my taste run toward urban intellectual. I don't want a trendy, popular name but classic names are boring (to me). What is good middle ground? I like names that can shorten to a cute nickname. Also, cannot start with B or M, last name starts with M. Thanks in advance!

Urban intellectual. I like the way you put that.
If you love Oliver, you might want to use it and pair it with an untraditional middle name that you could use as a first name, or using it as a middle name that he can go by.
Here's some ideas. Let us know if any of these are close and we can go from there.
Declan (Dec)
Daxton (Dax)
Ellis (Eli)
Silas (Cy/Si)
Riles (Ry)
Drakos (Drake)
Orion (O or Rye)
Camden (Cam)
Greysen/Grayson (Gray)
Grahmn/Graeme (Gray)
Wellesley (Wells)
Lincoln (Link)
Prescott (Pres)

Baby boy Maiford

Boy
Maiford
Caucasian/Hispanic
We want a hip unique name.
We don't like alliteration (another M).
We'd like to avoid common names (either traditional or too trendy). We'd like his name to stand out, but not too far that he'd get picked on!

Hip names that are classic but uncommon are great and it's smart to stay away from trendy names. The trick is finding a good name that doesn't sound weird. But if it stands out there's a chance no matter how awesome that kids will try to pick on it. The key is finding a name with no bad rhyming possibilities.
Here's a few ideas. Let us know what you like from this list and we can then zero in on that type of name.
Declan (nickname Deck)
Cannon
Lachlan (pronounced lock-lan) (nickname Lock)
Vaughn/Von
Kellan
Daxton
Zane
Ronan/Ronin
Beau/Bo
Bowie
Truman
Noble
Sloan/Slone
Ellis
Harris
Asa
Cole/Colm/Colman/Coleman
Enzo/Lorenza