Hey Skool Girl
I don't think I will ever be able to give up highwaisted Levi's. I know people hate them and guys think they are awful but there is just something about them (when worn correctly) that I adore. Goodwill is the place to score them. Making them DIY is the best, and cheapest, way to go. Mine cost $5.99 for Levi's pants that I then transformed into shorts.
Shorts: DIY Levi's
Shoes: DSW (old) similar here
Blazer: Andrea Behar/Boston Proper*
Sunglasses: House of Harlow
*items from Jane Pabon Boutique