I have completely fallen in love with the name but do you think it would age well or even suit a boy.
Other names i have been thinking of are [name_u]August[/name_u], [name_m]Ezra[/name_m], [name_m]Sy[/name_m] and [name_u]Emerson[/name_u].
If [name_f]Summer[/name_f] can be a girls’ name, then I definitely think [name_u]Winter[/name_u] can be a boys’ name! 
I love [name_u]August[/name_u] and [name_m]Ezra[/name_m]; [name_u]Emerson[/name_u] is nice but reminds me of a prog rock band DH loves and plays incessantly so that has tarnished it a bit for me! [name_m]Sy[/name_m] is okay as a NN but I think a two-letter name wouldn’t seem right to me.
I guess it would be usable but honestly I see it more as a middle name for boys.
I know a [name_u]Winter[/name_u] but is a girl of high school age. I think it would be a difficult name for a boy to wear but if you love it, I would put it in the middle spot. I really do like [name_u]August[/name_u] on your list and I think [name_m]Silas[/name_m] with the nn [name_m]Sy[/name_m] would be great.
[name_u]Winter[/name_u] is 100% usable for a boy.
Yes, I can see [name_u]Winter[/name_u] on a boy! I have met a male with the NN [name_u]Win[/name_u], so that works in your favor.
From your list I would choose [name_m]Ezra[/name_m].
Definitely usable. Nicknames [name_u]Win[/name_u] or [name_f]Winnie[/name_f] (the latter would work on a little boy, maybe not so much when he’s a teenager).
Would pair it with more of a traditional, masculine middle and definitely not another word name.
[name_u]August[/name_u] - no, too wordy
[name_m]Ezra[/name_m] - yes
[name_m]Sy[/name_m] - not my style, but nothing wrong with it I guess
[name_u]Emerson[/name_u] - no, too unisex. [name_u]Winter[/name_u] [name_u]Emerson[/name_u] could be a girl and I would probably assume it was!
I would use it as a MN for a boy but maybe not a FN. I think it is fine for a FN, but a personal preference I wouldn’t use it.
[name_m]Ezra[/name_m] [name_u]Winter[/name_u]
[name_m]Silas[/name_m] [name_u]Winter[/name_u] – nn [name_m]Sy[/name_m]
[name_u]Emerson[/name_u] [name_u]Winter[/name_u] - could be a girl’s name as well though.
(I just wouldn’t do [name_u]August[/name_u] [name_u]Winter[/name_u] – month/season combo)
I like [name_m]Ezra[/name_m] [name_u]Winter[/name_u] or [name_u]Emerson[/name_u] [name_u]Winter[/name_u]. I think it would be usable for a first name for a boy as well although just a little unusual. Not that that’s a bad thing
I have long loved [name_u]Winter[/name_u] for a girl, but, that being said, I’m really coming around to it for a boy! A former coworker of mine knew a guy named [name_u]Winter[/name_u], and she didn’t seem to think it was odd at all. I don’t think I would, either, honestly. I grew up with a lot of kids with super unusual names (in fact, it was more the norm to have an unusual name than a common one), so it’s just something you accept and get accustomed to. Sure, [name_u]Winter[/name_u] is now on the SSA list for girls (although I don’t know how high it ranks), but I still think it’s usable for boys. Your whole list is fabulous, though, so I’m sure whatever name you pick will be brilliant! If you end up not using [name_u]Winter[/name_u] as a FN, I think it’d make a cool MN, too. I think something like [name_u]August[/name_u] [name_u]Winter[/name_u] or [name_m]Ezra[/name_m] [name_u]Winter[/name_u] would be really cool.
Good luck!
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Eeeehhhh…
Technically it really should be unisex. After all, seasons don’t have a gender and neither do plant life or weather. And yet I’d still advise against naming a boy [name_f]Autumn[/name_f], [name_f]Summer[/name_f], [name_f]April[/name_f], [name_u]Rain[/name_u], [name_f]Ivy[/name_f], [name_f]Lavender[/name_f], or [name_f]Rose[/name_f]. I’m afraid [name_u]Winter[/name_u] falls into this category for me. I can only hear it as a girls’ name - particularly as the most obvious diminutive, [name_f]Winnie[/name_f], feels decidedly feminine.
The numbers from last year paint this picture, too: 553 girls named [name_u]Winter[/name_u], 35 boys. So while it does have a little use on the boys’ side, I think it would be a pretty bold move on your part and definitely not something I’d choose for my own son. I don’t know how well it would wear.
Interesting middle potential, though. [name_u]August[/name_u] [name_u]Winter[/name_u] or [name_m]Ezra[/name_m] [name_u]Winter[/name_u], maybe?
Totally useable!