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I like it with more intricate names (so not Taylor or Kate). I haven't thought about it much on a boy, but I think it's nice either way.

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Winter Katherine
Winter Seraphina
Winter Gwendoline
Winter Guinevere
Winter Tinuviel
Winter Siobhan
Winter Luciana
Winter Saxifraga
Winter Eglantine
Winter Heulwen
Winter Ariadne
Winter Andromeda
Winter Theophania
Winter Lysandra
Winter Leocadia
Winter Leontine
Winter Esmeralda
Winter Opaline

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Sebastian Winter
Bastian Winter
Osmund Winter
Olearius Winter
Lorcan Winter
Antonio Winter
Claudius Winter
Tiberius Winter
Octavius Winter
Octavian Winter
Vittorio Winter
Vincenzo Winter
Theophilus Winter
Alastair Winter