DH and I are at a constant stand still for our boy. His sister is Winter Eurydice. I’ll include reasoning behind each name.
My top 4 in order are:
August - (For the same reason Winter is Winter, we used to teach and his favorite students name was Winter while mine was August. Also, awesome namesakes.)
Dexter - (I’ve just always loved the name and envisioned it being my sons name.
Teddy - DH’s name is Eddy Jr. he doesn’t want a junior himself but proposed blending our names to get Teddy, my name is Tiana.
Jack - Our surname rhymes with Jack. My only hesitation is my biological fathers surname is Jackson and I don’t want any misconceptions to arise.
My husbands in order are:
Teddy
Jack
August
Dexter
However we’re constantly throwing out alternatives. I suppose we’re trying to decide if we should go sentimental or throw out a wild card.
(One edit: we’ve had the mind to make Teddys middle name Beres, an added layer of meaning as MIL’s favorite singer was Teddy Pendergrass and my mothers is Beres Hammond. This makes it feel more real while also adding hesitation as people might not take us/him seriously or so I’ve been lead to believe. No other name has a middle name yet.)
[name_f]My[/name_f] favorite is [name_u]Dexter[/name_u] - such a cool guy name, I’ve always loved it as well.
[name_f]My[/name_f] second pick would be [name_u]August[/name_u], getting very popular at the moment but for good reason, it’s an awesome name.
I love [name_u]August[/name_u] and [name_u]Teddy[/name_u] for you!
[name_u]August[/name_u] and [name_u]Winter[/name_u] may be a little matchy together, with one being a season and one being a month, but I think they go along together so well it almost doesn’t phase me!
[name_u]Teddy[/name_u] seems to be the most sentimental to you guys though, and I love that it’s a combination of your names!
[name_u]Teddy[/name_u] [name_u]August[/name_u] would make a great combo of the 2 names if you don’t already have a middle name in mind. It’s so soft and sweet, and it takes away the matchiness of [name_u]August[/name_u] and [name_u]Winter[/name_u], whilst putting the sentimental [name_u]Teddy[/name_u] up front. [name_u]Teddy[/name_u] and [name_u]Winter[/name_u] sound so sweet together too. Maybe not the best flow stylistically, but they still work together in their own way.
I’d avoid [name_u]Jack[/name_u] due to your hesitations and it rhyming with your surname. And [name_u]Dexter[/name_u], I mean, it’s just not my favorite for a kid. That may be because it’s my dog’s name though, so I can only envision it on a dog lol
With [name_u]Winter[/name_u] my favourites are [name_u]Dexter[/name_u] or [name_u]August[/name_u] - but if you choose [name_u]August[/name_u] and end up with more you have created a kind of season/month theme and [name_u]Dexter[/name_u] an -er theme
I also really like [name_u]Teddy[/name_u] as a name and for you for the reasoning
[name_u]Jack[/name_u] would be my vote to lose because it’s a nice name but it’s sooooo popular, your other options are so much better
Is there any chance at [name_u]Dexter[/name_u] [name_u]August[/name_u] or [name_u]August[/name_u] [name_u]Dexter[/name_u]? That would balance sis’s name the best, I think!
[name_u]Winter[/name_u] and [name_u]August[/name_u] together would be funny for me - as I’m in the southern hemisphere and [name_u]August[/name_u] is in winter here.
I would avoid [name_u]Jack[/name_u] completely for the reasons you listed.
[name_u]Dexter[/name_u] is good if you don’t mind the shared ending with [name_u]Winter[/name_u].
I think [name_u]Teddy[/name_u] sounds like the best option and I love that it’s a combination of your two names.
One thought - you could use [name_u]Dexter[/name_u] with [name_u]Teddy[/name_u] as the nickname, as it contains the letters t, e and d. It’s a bit of a stretch but it could definitely work, and that way you and your husband each get your favourite name.
[name_u]Winter[/name_u] [name_f]Eurydice[/name_f] and [name_u]Dexter[/name_u] “Teddy” [name_u]August[/name_u] - sounds great!
I would eliminate [name_u]Jack[/name_u]. It would sound too much like [name_u]Jack[/name_u] [name_m]Black[/name_m] with your surname.
I like the sentiment behind [name_u]Teddy[/name_u], but it just doesn’t seem like a name worthy of a spot on the birth certificate to me. It makes a great nickname though. [name_m]Theodore[/name_m] nickname [name_u]Teddy[/name_u]?
[name_u]Dexter[/name_u] is super cool and if you’ve loved it that long, it would be hard for me to pass up.
[name_u]August[/name_u] is my favorite. I love the stories behind you choosing [name_u]Winter[/name_u] and [name_u]August[/name_u]. Plus I love how they subtly go together. It’s almost a theme, but not really. I think they’re perfect siblings. [name_u]August[/name_u] [name_m]Theodore[/name_m] would be super cute.
[name_u]Winter[/name_u] [name_f]Eurydice[/name_f] is magical
[name_u]August[/name_u] is lovely - gentle, warm and charming
[name_u]Dexter[/name_u] is pretty cool and solid; well established with a hint of the modern
[name_u]Teddy[/name_u] - a very sweet way to honour you both while giving him his own name. [name_u]Winter[/name_u] and [name_u]Teddy[/name_u] are also the sweetest together!
[name_u]Jack[/name_u] - it doesn’t really sparkle with [name_u]Winter[/name_u], I wouldn’t want a name that rhymed with my surname and if you don’t want to use a name that could accidentally honour your bio father, I’d avoid this
Over all, [name_u]August[/name_u] is my fave, followed by [name_u]Teddy[/name_u]!
[name_u]August[/name_u] [name_u]Teddy[/name_u] or [name_u]Teddy[/name_u] [name_u]August[/name_u] would be lovely
I really like [name_u]August[/name_u], [name_u]Dexter[/name_u], and [name_u]Teddy[/name_u]!
I think if [name_u]Jack[/name_u] has a connection to your biological father like you said, then at least a few people will probably make the association. So if that’s important to you, I wouldn’t use it for that reason.
I like really like [name_u]Dexter[/name_u] [name_u]Teddy[/name_u] as a first and last name! I think [name_u]Dexter[/name_u] being a cool, hip first name and [name_u]Teddy[/name_u] being a soft, gentle middle name makes a really nice combo. Then you get the first name you’ve always loved and envisioned, while still using [name_u]Teddy[/name_u] to honor you both!
Congratulations! [name_f]My[/name_f] absolute favourite is [name_u]August[/name_u]. [name_u]Teddy[/name_u] is sooo cute , but it’s a bit too adorable for me, and with Beres it would really look like a [name_u]Teddy[/name_u] [name_u]Bear[/name_u], so I’m just not sure if it would age well.
I would take Jsck off the list, it’s a cool name but I wouldn’t want a rhyming name and it seems there are other misgivings with it.
I would choose:
[name_m]Edmund[/name_m] Beres nn [name_u]Teddy[/name_u] (I prefer [name_u]Teddy[/name_u] to any of the [name_u]August[/name_u] nicknames but I also think a full name is worthwhile - [name_u]Edward[/name_u] or [name_m]Theodore[/name_m] being two other obvious possibilities)
But I agree that it’s worth avoiding the risk of Teddy-Bear. So, how about:
[name_m]Edmund[/name_m] [name_u]August[/name_u] nn [name_u]Teddy[/name_u]
I like [name_u]Dexter[/name_u] and the idea of [name_u]Teddy[/name_u] as a nickname too. But I would go for [name_m]Edmund[/name_m] or [name_u]August[/name_u].
I love [name_u]Dexter[/name_u] and [name_u]August[/name_u] for you. [name_u]Dexter[/name_u] [name_u]Teddy[/name_u] or [name_u]Dexter[/name_u] [name_u]August[/name_u] would be my favorites
It’s really sweet to want to honour your MIL and Mum with their favourite singers, but I’d avoid [name_u]Teddy[/name_u] Beres, it just makes me think [name_u]Teddy[/name_u] [name_u]Bear[/name_u] and I’m not sure he’d appreciate that?
I also agree with others that [name_u]Teddy[/name_u] is too cutesy by itself, even without Beres in the middle… it feels like it would need a full name like Edmund/Edwin/Edward or [name_m]Theodore[/name_m].
I love [name_u]August[/name_u] and [name_u]Winter[/name_u] together but they are both times (month and season).
I know it’s down at number 4 on your partner’s list but [name_u]Dexter[/name_u] seems best? [name_u]Dexter[/name_u] [name_u]August[/name_u]?
[name_f]My[/name_f] absolute favourite is [name_u]August[/name_u]. 
[name_u]Teddy[/name_u] is sooo cute