While WTVOX reports that the stylish hoodie under a blazer is an outfit that would be difficult for you to mess up, there are a few things you should keep in mind before trying the unexpected trend the first time. First, nearly any hooded sweatshirt can fit under a boxy jacket. However, if you have a more tailored version, you could also pair it with a fitted hoodie. According to Unfused, the modern street style mixes formal clothing with casual to create something unique. 

Whether you choose to wear a luxury hoodie or something a bit more affordable, you should consider a darker, solid-colored hooded sweatshirt to keep the look sleek, especially when pairing it with a tailored blazer. Second, Unfused suggests wearing the same color for both layers with lighter-colored pants for a slightly more casual look. However, Who What Wear also indicates that a sleeker, lighter-colored ensemble can elevate the style.

Slacks, jeans, shorts, or skirts work for this trend, and the nice thing is, if you get lighter-weight pieces, you can wear them in warmer weather, too, saving heavier layering pieces for the cooler months (via Who What Wear). Of course, as with any fashion trend, you should feel comfortable with your outfit, first and foremost.