It’s back to school for teachers and children around the country and for Billy Madison too. This 1995 comedy was a fun take on what it would be like to repeat your entire education spending just two weeks per grade. We love all the quotable lines and Billy’s casual style. We took inspiration from his look to create a modern, more feminine version.

The key piece to Billy’s look is his plaid shirt. We took that idea and morphed it into a plaid shirt dress. Not only does it show off a woman’s curves, but it can be buttoned high or low depending on your comfort level. And who knew plaid could be sexy?

Next we added a short brown boot to the dress to play off of Billy’s practical work boots. These shoes have both masculine and feminine qualities to them which make them perfect for this outfit. We also accessorized with a baseball style cap but chose one that was quilted to give it a unique edge. Lastly we added a blue crossbody bag to keep some minor school supplies and maybe an apple for Ms. Vaughn.

Check out this great crossbody bag and other clothing and accessories at Chicastic.