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Wedge Sneakers
As this athletic shoe doesn't actually work in athletic situations, don't be afraid to pair it other slightly sporty pieces—no one will think you're coming from the gym. The overall effect will be streamlined and sleek enough for a Saturday night party. (During which all your uncomfortable stiletto-clad friends will be so very jealous.)
Trainers
Never, ever, EVER wear actual workout shoes with blue jeans or work trousers—you'll look like a misguided commuter who just switched out of her heels. Picking printed pants and bright accessories instead will make even the sneaker-iest of sneakers look like an intentional statement.
Tennis Shoes
Canvas kicks are a great way to make even the frilliest, girliest sundress in your closet seem tomboy-ish and cool. It's also a foolproof way of pulling an acceptable summer outfit together in under five minutes.
High-tops
These are best with cropped skinny jeans since the tapered leg highlights the shoe's shape. Up top, keep things casual: the goal is to look effortless in an "Oh, I just grabbed the first thing in my closet and it happened to be awesome" kind of way.