Winter Lynn nn Winnie--- I like!
Katherine Jessamine nn Kit----Prefer Catherine with a C as I love Cate better with a C but a nice name either way
Willa May ----I like this, underused differnt, I think the little Willas of the world will spend a lot of time explaining they are not WIllow
Adela- Love! We were tossing around Adeline for a while and said we would call her Della.
Violet -- i think this name is pretty in theory but i see VIOLENT everytime i read it.
Kenna (really like this name but DH's sister's name is Kendra and we do not want it to be an honor name lol.)----Not a fan
How about Kirrily in stead of Kenna?
Winter is a great, modern name. However, the recent attention/buzz it seems to be receiving coupled with its first appearance last year on the Top 1000 might spell the makings of a fad, so that's something to be mindful of if you worry about that.
Willa is lovely too - vintage feminine without being frilly. I love all the W-names, really: Winter, Winifred, Willa, Willow, Winslow, Wendy, Wilhelmina...
Violet is a classic and Nameberry favorite. Of all the names you listed, this would probably be the least controversial. That's not necessarily a good reason to choose a name, but it doesn't hurt.
Not as fond of Kenna, but I think I'm just tired of the K-name trend in general, which in coming decades will be timestamped as very particular to the late 90s/early 2000s. But if it's a name that has meaning for you, go for it! :-)
And Katherine isn't trendy, so it escapes that association (although I prefer Catherine); I like it, but as far as classic/vintage names go, I prefer Willa and Violet. And Winter is just cool.
Winter Lynn nn Winnie.........I like Winter better for a boy and do not care for the nn winnie (read pooh into that and a horse)
Katherine Jessamine nn Kit.....LOVE the nn Kit! Katharine is good. I agree with some others that Jessamine might be too much with it
Willa May .....Willow May would be better
Adela.....Good solid name that is nms
Violet ----One of my (new) favorites. It says Spring and fresh and sweet for a girl and aso evokes creativity.
Kenna I like how this sounds and even if you do not think of it as an honoring name maybe SIL will and be secretly pleased? I named my first son Patrick (in the Hospital after he was born and I saw him for the first time) My SIL thought I named him for her and I never told her differently. I never even thought of her when I named him!
Thanks for all the great feedback, ladies!! Winter has been a very long-standing favorite of mine and my husband loves the nn Winnie. I've been trying to convince him to let us go with Gwendolyn nn Winnie but he knows a girl named that who he doesn't care for. I honestly do not like Lynn, but it is a big honor name as it is my, and my mother's middle name. I thought the unusual Winter paired better with Lynn than, for example, Katherine Lynn.
I never thought of Willie Mays (ie Willa May)!! And honestly Violet is my current favorite right now but I am very worried about it's current popularity and it's potential to get into the top 10. However, I just think it's a perfect name! I honestly don't like the name Katherine very much but love the nn Kit and can't come up with any other names Kit could be short for. Keep the comments coming!
Winter Lynn nn Winnie - This is a pretty choice and Winnie is such a great retro name, but Lynn is killing it.
Katherine Jessamine nn Kit - I love Katherine - classic and elegant, not so sure about Jessamine, it's quite a fussy name and when paired with Katherine neither of these names shine. Kit is terrific as a nn.
Willa May - Willa isn't my naming style but it's pretty and May is very sweet. Personally I wouldn't put them together, it's a bit Southern Belle.
Adela - Not my favourite, I think it's quite confusing, i'm not sure how to stress it.
Violet - I like this name, vintage but fun sounding.
Kenna - Too close to Kendra.
Winter Lynn nn Winnie - I like the nn Winnie, however I think that Winifred is better to get Winnie imo.
Katherine Jessamine nn Kit - This is pretty, love the classic first name and the middle is nice, plus it has a spunky nn of Kit!
Willa May - Willa May is very beautiful, simple and stunning!
Adela - I much prefer Adele or Adeline
Violet - This is on my top 5 list, it's gorgeous, plus I know the most wonderful woman named Violet
Kenna - There is a itty bitty town (well it's actually a village) near my home called Kenna, I like it.
So here is what I think. If Winter has been a long time favorite for you and your husband likes the nn Winnie then you should use that one. That way you know that it is not a name that you like now but will decide you that don't like it two days before she is born. I think the name Winter/ Winnie is adorable! I understand the whole using the middle name as a tribute thing since my mn, my moms mn, and my great grandmas mn is Anne. I have names that I would love to use more but I want to pass it on at the same time. If you didn't decide to go with Lynn, what about Winter May? If you liked Willa May (which is also adorable by the way!) but loved Winter more, what about just using May with Winter?
As for the other names, I would say that if you are worried about Violet's popularity at all, don't use it. I can see that one becoming really popular in the future. I love the nn Kit!! If you didn't use Winter that would be my second vote but what about just using Kit by itself versus as a nn since you said you don't really like Katherine that much? Just a thought. I hope this helps a little!