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For When You're Wearing: A cocktail dress in a bright summery color.
For When You're Wearing: A little black slipdress.
For When You're Wearing: A full-skirted, tea-length dress. Together it'll look so feminine and Betty Draper-y.
For When You're Wearing: A simple black or white dress and you want a jacket that makes it seem like more of a complete look.
For When You're Wearing: A dress that you don't want to pair with a black jacket—like an orange one, because the combo would be kinda Halloween-ish.
For When You're Wearing: Something in the nude or white family, so you can go for a '90s Calvin Klein-y look.
For When You're Wearing: A white dress and you don't want to go for the white-and-black pairing. Instead, go for lighter accessories, like nude heels and this little jacket.
For When You're Wearing: A knee-length dress in bright pink, because pink and red make such a color color combo.
For When You're Wearing: A maxi dress, because cropped jackets work really well with those proportions.
For When You're Wearing: A bright-colored mini dress.
For When You're Wearing: Soft florals and you want something pretty and feminine.
For When You're Wearing: A full, pleated skirt and strappy heels, because the notch in the lapel will give it a cool structured contrast.
For When You're Wearing: A white dress and white shoes. White on white always looks crisp.
For When You're Wearing: Any dress that you'd almost pair with a black blazer with real lapels if it didn't feel too corporate. The drapey hem gives this the shape of a cardigan with the polish of a blazer.