There are certain styles that transcend age and era. Nick Blake, owner and operator of Desmonds, created three similar looks for three generations. 

Opting for a more casual version of the classic button-down, the “hangin out” shirts by johnnie-O offer a more comfortable way to look and feel great. Paired with quality denim and genuine leather, men of any decade can pull off this sophisticated, yet functional, style.  

“Hangin Out” Button-Down Shirts, johnnie-O, $98-$115 

Denim, 34 Heritage, $165

Denim, Liverpool, $89 

Leathers, Scully and Missani, $475-$525