It's a family name for me and I've thought about using it as a middle name but I find it way too awkward as a first name. I'm not opposed to it personally but I'd feel self-conscious telling someone that was my kid's name because it is commonly held up as the prime example of an "ugly" name with Gertrude and the like. I'm all for strong female names but Winifred kind of sounds bumbling to me rather than strong sometimes? Almost cartoonish?
I like Win and Winnie and many other nicknames. I just know I wouldn't like to introduce myself as Winifred myself, not even a little bit. I can't picture it on a young adult woman trying to find her way in the world at all. I just can't.