There's something to be said about knowing what works for you and sticking to it. Normally for me it's a shorter skirt and my all too-familiar silhouette of a fitted top and fuller skirt. When I wear this skirt I nearly always style it the same way (see the last picture of this post). Summer to winter things don't change that much except the scenery and amount of layers I'm required to don. I, naturally, wore a coat on top of this but as my winter posts are coat dominated I briefly shed it for the sake of a few photographs. Also, flats only work when we have a fresh dusting of snow, once everything compacts and melts and re-freezes into an icy mass I stick to boots. It might not always look like it, but I do attempt to dress practically for the weather conditions.
Outfit details:
Gardens of Whimsy headband
vintage cardigan (similar)
vintage cardigan (similar)
slip dress (worn as top)
vintage belt
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