20. The Navy Blazer — Where would we be without this piece? Seriously, these blazers are so optimal because you can stuff them in your bag and smarten up a look in a snap. A favorite travel companion, we also love the navy blazer's timeless aesthetic and ability to slim down any extra-poundage you may still be Barry's Bootcamping away.

Windsor Custom For Safira Nautical Blazer, $675, available at Safira; Frank & Oak Terry Blazer in Navy, $95, available at Frank & Oak.