There's something quite classic about a plaid dress and a (faux) leather jacket; it's an oft-repeated combination but as with many popular things, there's a reason for it. It's such an easy combination and nearly always looks good--a tougher jacket is the perfect counter-balance to a preppy or more classic plaid. That sort of balance is how I like things. I don't want to interpret vintage pieces too literally or style a frilly dress in a very saccharine manner, although I still haven't managed to look completely edgy yet...maybe one day.
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