Newsboy

You don't have to have a paper route to wear a newsboy cap, actually, you probably wouldn't be able to even afford one if you did. Newsboy caps are an easy way to make yourself look a bit more distinguished, even with a simple T-shirt, you'll look like a boss. Try this lightweight version from Brixton, and you'll be all set for any occasion. 

Brixton Barrel Cap
Buy It Now at Brixton, $34

Miansai by Michael Saiger Tiller Bracelet
Buy It Now at Miansai, $185  

Apolis Global Standard Issue Shorts
Buy It Now at Apolis, $168