We have two seasons in Northern California -- dry & wet. It's dry from about May through October, then wet off & on during November to April. Unless there's a drought, which seems to happen every five years or so. Right now, it's wet. Raining every few days for the past month or so. Which typically means lots of sweaters & boots in my wardrobe, but today I pulled out a sundress from last summer & figured out how to make the transition from summer-wear to winter.
What I'm wearing:
Black long-sleeve T-shirt, Old Navy
Purple print cotton sundress, Target
Black leggings, American Apparel
Black spool-heel, lace-up boots, Target
Black elastic belt with silver flower, NY & Co.
Silver ball choker, Target
Onyx drop earrings, vendor on Telegraph Ave. in Berkeley
Raisin Rage lipstick, Revlon (I've been wearing this color since high school!)
The key to wearing a sundress in winter is, imo, the color. Dresses in bright colors with bold patterns (or solid colors) look more appropriate to the colder months than light colors & delicate prints. The later says "springtime" tho' I suspect it could be made to work in a vintagey way with very careful choice of accessories. But it wouldn't be easy.
The two classic modes for working a sundress into your winter wardrobe are (1) layer over long-sleeves, as I did here or (2) layer under a sweater or jacket. The first method works best if the dress has sleeves or wide straps. Don't do it with little spaghetti straps because that just draws attention to the fact that you're wearing a summery dress. Put narrow-strap dresses underneath a buttoned sweater or jacket.
Tights & boots are a must with a sundress to really ground the look. Chunky heels or flats might work, but a heavy shoe really helps contrast the lightweight fabric of the dress. I went for leggings today because it's cold!
Heavyweight accessories like a chunky necklace or bracelet, a wide belt, or a scarf also add dimension to the look. But go for balance if you're wearing a jacket (then again, I'm a "more is more" gal ;-).
Have you tried transitioning a garment from one season to another? Successes or failures? Tips, tricks?