I was asked where my next vacation will be and although we have yet to talk about where we will go on our first vacation, I know that it must be perfect for sun so that there's tons of beach time! If I had to choose super cute items for him to wear, I'd go with this - only he could say whether he would wear some or all of these but I am super excited that I think he would definitely wear it! I'm a huge fan of Mosley Tribes which is a fab old school vibe that he could rock. You always have to have a bag as sometimes not all of my items fit in my tote but how can you now love this Ben Sherman bag available at Asos. A party isn't a party without these Fyasko boardshorts which are super retro and of course I LOVE this Robert Graham Fedora which ties in the amazing color story that is going on here. Of course to complete the look would be a cigar of course!