Okay, Hannah Montana may not have anything to do with this Fashionisto’s look, but hey those lyrics are oh-so catchy and are relative to his collared shirt. On a rainy day like today, it’s too easy to burrow away in your comfy sweats and sneakers, but I admire this Fashionisto’s perseverance. Classically relaxed is definitely the way to go. From his collared shirt, to his comfortable zip-up sweatshirt and lastly to his stylish accessories, he knows how to dress for success on a damp day.

Collared shirts are the best choice for any guy because they can easily be dressed up or down depending on the occasion. While they’re perfectly acceptable and expected for more formal events, they are even better for a casual day like heading to class. They are a step above a T-shirt yet not too professional where it becomes stiff. By layering a cozy sweatshirt on top, this helps to echo the relaxed look.

By pairing this effortless and presentable look with a dynamic duo of accessories, this Fashionisto is all set to start his day. This Fashionisto’s watch is eye-catching and also seamlessly flows with the rest of his look. Like a collared shirt, the watch is also versatile where it can be worn either for a formal or an informal event. Same goes for the boat shoes. The best part about boat shoes is how comfortable they are, yet they also dress up any look and are appropriate for many events. A win-win in my book. This Fashionisto perfectly captures a comfortable rainy day look with his combination of dressy pieces matched with more relaxed items.

How To: Heading to a meeting with your professor? Have no fear! A collared shirt is the way to go. Depending on the topic of the meeting, you can either match your button-down with a pair of jeans or khakis. Follow this Fashionisto’s lead for accessories and you’re ready to go.