Well, that was difficult to choose!
I’m just going to give you my favorite to least favorite rankings and thoughts. So many great choices!
Alden-I wouldn’t say it’s my absolute favorite on the list, but it’s my favorite that’s also as interesting of a name as Winrey. It’s just soft, thoughtful, but still kind of outdoorsy. It also sounds old fashioned. It’s really simple yet really unique. Has all of the good qualities! And if you want a nn, I think that [name_f]Winnie[/name_f] & [name_m]Ace[/name_m] would be so cute.
August-This may be my favorite in general from the list, but I’m hearing it more these days & it’s because a bit less special. It’s still a great name. It’s like [name_u]Alden[/name_u] in that it sounds vintage. It’s smart & gentle, but outdoorsy too. [name_f]Winnie[/name_f] & [name_m]Augie[/name_m] or [name_f]Winnie[/name_f] & [name_u]Gus[/name_u] are perfect.
Maxwell-This is just the right amount of quirky & charming. It’s simple, smart & friendly. I love the sporty sophisticated vibe of [name_u]Max[/name_u]. It is really popular, unfortunately.
Milo-So sweet. It’s quiet yet spunky at the same time. It’s simple & old fashioned. Gaining popularity a bit, but not too bad. Goes well w/Winnie.
Sullivan-It’s not my absolute favorite name, but I think that it evokes a similar vibe as Winrey. Plus, [name_u]Sully[/name_u] is adorable.
Nicholas-It’s a handsome solid classic, but just kind of over done that past 40 years. That’s a long time! Sounds a bit dated. I do love the nns [name_u]Nico[/name_u], [name_m]Cole[/name_m] or [name_m]Nils[/name_m].
Simon-Really cute & classic. I kind of like it, but some days I feel like it sounds geeky.
Sawyer-I like it, because it gives me a cool cowboy vibe. And then sometimes I am lukewarm to it, because it gives me a snobby prep school boy vibe. [name_m]Can[/name_m]’t explain that one, though.
Foster-Doesn’t do much for me, but it’s fine.
Wallace-I think it’s interesting & definitely old man-ish. Which is fun. But I just don’t love the sound. It reminds me of walrus.
Roscoe-It’s different & sort of exotic. [name_m]Just[/name_m] can’t get into it.
Felix-I don’t hate it, but it just sounds a teeny bit goofy.
Roland-It’s fine, but doesn’t do much for me.
Shepherd-It has a nice sound, but too much of a word & not as much of a name. It totally is a name. I just can’t personally get used to it as one.
Adler-Not sure why, but I don’t care for the way this sounds.
Remington-This is too stuffy, even though I think that [name_u]Remy[/name_u] is dashing.
Miller-Meh. It’s just a beer name & a last name. I don’t care for it for a boy fn.
Hope this helps. 
And Winrey is an adorable name too! 
