Get a running start on the athletic aesthetic with the varsity jacket (our pick: Coach, $1,098; coach.com). Instead of committing to a full-on sport-inspired theme, layer it with a LBD, like Emma Roberts.
Instead of the usual pleats, try a fit-and-flared skirt on for size (we like Le Fou by Wilfred, $60; aritzia.com). Pair it with a casual tee or, for a more polished spin, a printed blouse like Olivia Palermo's.
Add some flair to your wardrobe with amped-up tees. This one by Rebecca Taylor ($195; rebeccataylor.com) achieves the right amount of glam. Take a cue from Jaime King and pair it with distressed jeans.
Dressed-up shorts, like these checkered ones ($25; mango.com) speak to a sophisticated side. Copy Nikki Reed and tailor the look for the workplace with a pair in a conservative black and white print.