This Paul Smith print may look like misshapen polka dots from afar, but up close, it reveals dainty, Carmen Miranda-inspired pineapples. Roll up the sleeves, tuck it into some Topman chinos, and finish the look with a belt stolen from your boyfriend’s closet.
A soft T-shirt is just the excuse we need to go to New York’s Saturdays surf shop, where the employees are as easy on the eyes as the clothes (another great reason to shop menswear). Layer Pyrrha necklaces over it and top with a Block straw hat.
Plaid button-ups aren’t just for lumberjacks and hipsters. The small sizes at Brooklyn Tailors, J.Crew, and Jeremy Argyle fit our frame just right, though we don’t recommend wearing more than one at a time (as shown).