The best thing to what to wear with orange plaid shorts is definitely anything that comes from the prep's wardrobe. Because of their unorthodox color and bold pattern, orange plaid shorts already encompass two, important properties of the prep's wardrobe, so it makes perfect sense to throw some additional prep clothes on your person. Prep clothes really make the man, so it is your good fortune to dress like a prep.
- Polo Ralph Lauren Men's Classic Fit Pony Polo Shirt. If you want to go prep for your look when you are wearing your orange plaid shorts, you can do yourself no bigger favor than by getting yourself the defining style of shirt that preps of all races love to wear: the polo shirt. With a beautiful placket, solid buttons that don't fall off and a mesh finish, this polo shirt just screams class and preppiness, making it a perfect companion for your orange plaid shorts.
- Polo Ralph Lauren Men's Kewzip II Oxford. The next thing you need to try to round off your prep look is a sweet pair of prep-like loafers, and there is no better candidate than this offering from Polo Ralph Lauren. Featuring the brilliant quality of loafers-which means you can just slip them on-these Men's Kewzip II Oxfords actually take the concept to the next level by including a smart, single zipper to give you extra support around your ankle. With leather materials and duck-stitch styling, this prep shoe is a great complement to your orange plaid shorts.
- Cable Tennis Sweater. If you are looking for the neatest way to complete your new-found and newly empowering prep look, then choose this cable tennis sweater to go with your orange plaid shorts. Long the go-to sweater and top for preppies of every race, color and creed, the cable tennis sweater is a very resourceful piece of clothing that not only looks classy and sophisticated, but it also gives you a sense of majesty and control that somehow compels total strangers into complimenting your wardrobe choice.